Tag: 200-300

2-Substituted-5-nitropyrimidines by the condensation of sodium nitromalonaldehyde with amidines was written by Fanta, Paul E.;Hedman, Edward A.. And the article was included in Journal of the American Chemical Society in 1956.Application of 51488-33-6 This article mentions the following:

p-MeC₆H₄C(:NH)NH₂ (I) (1.86 g.) and 1.57 g. Na[C(NO₂)(CHO)₂] (II) mixed in 25 cc. H₂O at room temperature gave I-II salt, fine white needles, m. 148-50鎺?(from H₂O), which, heated 2 h. at 70鎺?in aqueous Triton B, yielded 5-nitro-2-p-tolylpyrimidine (III), m. 217鎺? PhC(:NH)NH₂.HCl (IIIa) and II mixed in H₂O at room temperature darkened and resinified on standing and the product was characterized only by conversion to 5-nitro-2-phenylpyrimidine (IV) on heating in aqueous Triton B. IIIa.2H₂O and II.H₂O heated 4 h. with aqueous Triton B at 70鎺?gave 79% IV; IIIa and II heated similarly with aqueous K₂CO₃ gave 66% IV and with aqueous NaOH 42% IV (NH₃ evolved during the reaction); II and IIIa refluxed 4 h. with aqueous NaOH gave no IV but NH₃ was evolved during the reaction and BzOH was isolated from the mixture II and IIIa heated 15 min. at 80鎺?with Ac₂O-pyridine yielded 85% IV; a similar run but without the pyridine gave only 40% IV. II and IIIa refluxed 2 h. with EtOH and NaOEt, or kept 12 h. at 0鎺?with alc. HCl gave no IV. IIIa.2H₂O.HCl (1.94 g.) and 1.57 g. II in 25 cc. H₂O treated with 1 cc. Triton B, heated 4 h. at 65-70鎺? and refrigerated overnight yielded 1.50 g. IV, pale tan microcrystals, m. 222-3.5鎺? II (2.8 g.) mixed intimately with 1.8 g. MeC(:NH)NH₂.HCl, treated with a few drops piperidine, heated 1 h. on the steam bath, treated with 1 g. Na₂CO₃, heated 0.5 h., dissolved in a small amount of H₂O, the solution cooled, filtered, and the residue extracted with ligroine gave less than 1% 2-methyl-5-nitropyrimidine, m. 186-7鎺?(from ligroine); a similar run with NaOH in EtOH gave no better yields. II treated with concentrated NH₄OH or with NH₄Cl, NH₄OAc, or AcNH₂ in the presence of Triton B gave an intractable resin. The appropriate nitrile (0.5 mol) and 0.5 mol absolute MeOH treated with a slight excess of dry HCl in 25 cc. absolute Et₂O, and the resulting solid imidic ester HCl salt decomposed with 10% NH₃ in absolute MeOH gave the corresponding amidines which were isolated as their HCl salts and converted by the method described for the preparation of III to the corresponding 2-substituted-5-nitropyrimidines (V); in this manner were prepared the following arylamidine HCl salts and V (aryl group of amidine = 2-substituent of V, m.p. of amidine HCl salt, m.p. and % yield of V given): Ph, 70-3鎺? 222-3.5鎺? 79; p-MeC₆H₄, 215-16鎺? 249-50鎺? 87; p-MeOC₆H₄, 216-18鎺? 216-18鎺? 30; p-BrC₆H₄, 261-3鎺? 225-7鎺? 89; p-ClC₆H₄, 240-4鎺? 170-1.5鎺? 81; p-FC₆H₄, 209-11鎺? 154-5鎺? 71; p-O₂NC₆H₄, 294-5鎺? 235-7鎺? 48; p-H₂NO₂SC₆H₄, 207-9鎺? 268-70鎺? 41; p-PhC₆H₄, 245-9鎺? 253-4鎺? 85; m-O₂NC₆H₄, 238-42鎺? 133-4鎺? 79; 3,4-(MeO)₂C₆H₃, 234鎺? 182-3鎺? 67; 3-C₅H₄N, 190-4鎺? 202-3鎺? 36; PhCH₂, 151-3鎺? 170鎺? 77 (picrate, m. 228-30鎺?; 3,4-(MeO)₂C₆H₃CH₂, 153-5鎺? 235鎺? 38; PhCH:CH, 68-70鎺? 219-20鎺? 81; BzCH₂, -, 210-11鎺? 70 (free amidine, m. 185-7鎺?. The following aliphatic amidine HCl salts (alkyl group and m.p. given) did not condense with II: Me, 164-6鎺? Bu, oil (picrate, m. 193-5鎺?; C₁₁H₂₃, 125-7鎺? MeCH(OH), 162-6鎺? HOCH₂CH₂, 81-2鎺? IV (0.20 g.) in 0.40 g. NaOH in 10 cc. H₂O treated with warming and stirring with 1.05 g. Na₂S₂O₄, centrifuged to remove a small amount of brown solid, cooled to 5鎺? and treated with 2 cc. Ac₂O yielded the 5-AcNH analog of IV, shiny white platelets, m. 208-9鎺?(from 20% aqueous EtOH). IV (2.00 g.) in 200 cc. absolute EtOH hydrogenated 0.5 h. at room temperature and 3 atm. pressure over 0.6 g. 5% Pd-C, the suspension evaporated to dryness in vacuo on the steam bath, the residue extracted with boiling C₆H₆, and the extract cooled yielded 1.50 g. 5-amino-2-phenylpyrimidine (VI), m. 90.5-92鎺? Similarly was obtained 5-amino-2-(p-tolyl)pyrimidine, 95%, m. 183.5-84鎺? VI diazotized under various conditions and each reaction mixture tested for the presence of aromatic diazonium salt with an alk. solution of 2-C₁₀H₇OH in no case gave a color. In the experiment, the researchers used many compounds, for example, 3,4-Dimethoxybenzimidamide hydrochloride (cas: 51488-33-6Application of 51488-33-6).

3,4-Dimethoxybenzimidamide hydrochloride (cas: 51488-33-6) belongs to ethers. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides. Ethers feature bent C閳ユ彊閳ユ弲 linkages. In dimethyl ether, the bond angle is 111鎺?and C閳ユ彊 distances are 141 pm. The barrier to rotation about the C閳ユ彊 bonds is low. The bonding of oxygen in ethers, alcohols, and water is similar. In the language of valence bond theory, the hybridization at oxygen is sp3.Application of 51488-33-6

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Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Structure-activity relationship investigation for imidazopyrazole-3-carboxamide derivatives as novel selective inhibitors of Bruton’s tyrosine kinase was written by Zhang, Dandan;Xu, Guiqing;Zhao, Jie;Wang, Yue;Wu, Xiaofang;He, Xing;Li, Wei;Zhang, Shuting;Yang, Shouning;Ma, Chunhua;Jiang, Yuqin;Ding, Qingjie. And the article was included in European Journal of Medicinal Chemistry in 2021.Related Products of 54916-28-8 This article mentions the following:

BTK (Bruton’s tyrosine kinase) inhibitors are the most promising drugs for the treatment of hematol. tumors. A high selectivity of BTK inhibitors ensures reduced side effects from off-targeting. Accordingly, here, based on Zanubrutinib, we designed and synthesized a new range of I, II and III. as novel BTK inhibitors that retained the amide group for improved selectivity. These compounds revealed potent inhibitory activity against BTK in vitro. Remarkably, compounds I [R¹ = acryloyl, R² = R³ = H; m = 1, n = 2] (IC₅₀ 5.2 nM) and I [R¹ = but-2-ynoyl, R² = R³ = H; m = 1, n = 2] (IC₅₀ 4.9 nM) possessed the highest kinase selectivity. Both of these effectively inhibited the auto-phosphorylation of BTK, blocked the cell cycle in G0/G1 phase, and induced apoptosis in the TMD8 cells. In a TMD8 cells xenograft model, a twice-daily dose of compound I [R¹ = acryloyl, R² = R³ = H; m = 1, n = 2] at 25 mg/kg and a thrice-daily dose of compound I [R¹ = but-2-ynoyl, R² = R³ = H; m = 1, n = 2] at 15 mg/kg significantly suppressed the tumor growth without obvious toxicity. Collectively, I [R¹ = acryloyl, R² = R³ = H; m = 1, n = 2] and I [R¹ = but-2-ynoyl, R² = R³ = H; m = 1, n = 2] are the potential selective BTK inhibitors that can be developed further. In the experiment, the researchers used many compounds, for example, 1-(4-(4-Methoxyphenoxy)phenyl)ethanone (cas: 54916-28-8Related Products of 54916-28-8).

1-(4-(4-Methoxyphenoxy)phenyl)ethanone (cas: 54916-28-8) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. Ethyl ether is an excellent solvent for extractions and for a wide variety of chemical reactions. It is also used as a volatile starting fluid for diesel engines and gasoline engines in cold weather. Dimethyl ether is used as a spray propellant and refrigerant. Methyl t-butyl ether (MTBE) is a gasoline additive that boosts the octane number and reduces the amount of nitrogen-oxide pollutants in the exhaust. The ethers of ethylene glycol are used as solvents and plasticizers.Related Products of 54916-28-8

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

FeCl₃/PPh₃-catalyzed Sonogashira coupling reaction of aryl iodides with terminal alkynes was written by Sawant, Dinesh N.;Tambade, Pawan J.;Wagh, Yogesh S.;Bhanage, Bhalchandra M.. And the article was included in Tetrahedron Letters in 2010.SDS of cas: 75581-11-2 This article mentions the following:

Conditions for a FeCl₃/PPh₃-catalyzed and palladium-, copper-, amine free-Sonogashira coupling reaction of aryl halides with terminal alkynes are reported. The protocol was applicable to a wide variety of substituted aryl iodides and alkynes with different steric and electronic properties and gave excellent yields of the desired coupling products. In the experiment, the researchers used many compounds, for example, 4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2SDS of cas: 75581-11-2).

4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2) belongs to ethers. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides. Electron-deficient reagents are also stabilized by ethers. For example, borane (BH3) is a useful reagent for making alcohols. Pure borane exists as its dimer, diborane (B2H6), a toxic gas that is inconvenient and hazardous to use. Borane forms stable complexes with ethers, however, and it is often supplied and used as its liquid complex with tetrahydrofuran (THF).SDS of cas: 75581-11-2

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Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

C-5-Disubstituted Barbiturates as Potential Molecular Probes for Noninvasive Matrix Metalloproteinase Imaging was written by Breyholz, Hans-Joerg;Schaefers, Michael;Wagner, Stefan;Hoeltke, Carsten;Faust, Andreas;Rabeneck, Helmut;Levkau, Bodo;Schober, Otmar;Kopka, Klaus. And the article was included in Journal of Medicinal Chemistry in 2005.Application In Synthesis of 1-(4-(4-Methoxyphenoxy)phenyl)ethanone This article mentions the following:

Studies have demonstrated a pos. correlation between inflammation, metastasis, or atherosclerosis and the unbalanced or culminated expression of matrix metalloproteinases (MMPs). The mol. imaging of locally upregulated MMP activity in vivo is a clin. challenge. Actually, radioligands based on nonpeptidyl MMP inhibitors (MMPIs) are currently in development as putative radiopharmaceutical agents for the noninvasive in vivo assessment of activated MMPs. Nonpeptidyl MMPIs bind to the zinc active site of the activated enzyme via mono- (e.g. carboxylate) or bidentate (e.g. hydroxamate) complexation thereby exhibiting a broad-spectrum MMP binding potency. Thus, these mentioned endopeptidase inhibitors should be useable lead compounds for the redevelopment as diagnostic MMPI radiotracers. Recently, the non-hydroxamate C-5-disubstituted pyrimidine-2,4,6-triones were disclosed as subgroup-selective MMP inhibitors. We here describe a set of fine-tuned barbiturates as a new class of MMPI radiotracers for the noninvasive in vivo visualization of activated MMPs using scintigraphic techniques such as SPECT or PET. In the experiment, the researchers used many compounds, for example, 1-(4-(4-Methoxyphenoxy)phenyl)ethanone (cas: 54916-28-8Application In Synthesis of 1-(4-(4-Methoxyphenoxy)phenyl)ethanone).

1-(4-(4-Methoxyphenoxy)phenyl)ethanone (cas: 54916-28-8) belongs to ethers. The oxygen atom in ethers are more electronegative than carbon, thus the hydrogens which are alpha to the ethers are more acidic than the simple hydrocarbons. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides.Application In Synthesis of 1-(4-(4-Methoxyphenoxy)phenyl)ethanone

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Ab initio and density functional theoretical design and screening of model crown ether based ligand (host) for extraction of lithium metal ion (guest): effect of donor and electronic induction was written by Boda, Anil;Ali, Sk. Musharaf;Rao, Hanmanth;Ghosh, Sandip K.. And the article was included in Journal of Molecular Modeling in 2012.Application In Synthesis of 1,4,7,10-Tetraoxa-13-azacyclopentadecane This article mentions the following:

The structures, energetic and thermodn. parameters of model crown ethers with different donor, cavity and electron donating/ withdrawing functional group were determined with ab initio MP2 and d. functional theory in gas and solvent phase. The calculated values of binding energy/enthalpy for lithium ion complexation are marginally higher for hard donor based aza and oxa crown compared to soft donor based thia and phospha crown. The calculated values of binding enthalpy for lithium metal ion with 12C4 at MP2 level of theory is in good agreement with the available exptl. result. The binding energy is altered due to the inductive effect imparted by the electron donating/ withdrawing group in crown ether, which is well correlated with the values of electron transfer. The role of entropy for extraction of hydrated lithium ion by different donor and functional group based ligand was demonstrated. The HOMO-LUMO gap is decreased and dipole moment of the ligand is increased from gas phase to organic phase because of the dielec. constant of the solvent. The gas phase binding energy is reduced in solvent phase as the solvent mols. weaken the metal-ligand binding. The theor. values of extraction energy for LiCl salt from aqueous solution in different organic solvent is validated by the exptl. trend. The study presented here should contribute to the design of model host ligand and screening of solvent for metal ion recognition and thus can contribute in planning the experiments In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3Application In Synthesis of 1,4,7,10-Tetraoxa-13-azacyclopentadecane).

1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3) belongs to ethers. The oxygen atom in ethers are more electronegative than carbon, thus the hydrogens which are alpha to the ethers are more acidic than the simple hydrocarbons. At room temperature, ethers are pleasant-smelling colourless liquids. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil.Application In Synthesis of 1,4,7,10-Tetraoxa-13-azacyclopentadecane

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthesis and bioactivity of erythromycin derivatives was written by Chen, Mingwei;Muri, Estela M. F.;Jacob, Melissa;Williamson, John S.. And the article was included in Medicinal Chemistry Research in 2003.Recommanded Product: 1,1-Diisopropoxycyclohexane This article mentions the following:

A small series of semisynthetic 6-O-alkylated erythromycin derivatives were synthesized and evaluated for their antimicrobial activity. A dichlorobenzenyl 6-O-allyl erythromycin derivative (I) was found to be active against Cryptococcus neoformans (IC₅₀ 5.0 娓璯/mL), Staphylococcus aureus (IC₅₀ 5.0 娓璯/mL), and methicillin-resistant S. aureus (IC₅₀ 5.0 娓璯/mL). In the experiment, the researchers used many compounds, for example, 1,1-Diisopropoxycyclohexane (cas: 1132-95-2Recommanded Product: 1,1-Diisopropoxycyclohexane).

1,1-Diisopropoxycyclohexane (cas: 1132-95-2) belongs to ethers. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. At room temperature, ethers are pleasant-smelling colourless liquids. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil.Recommanded Product: 1,1-Diisopropoxycyclohexane

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthesis and conformational structure of hydrazo-bridged homo calix[2]pyridine[2]triazines was written by Liang, Dong-Dong;Wang, Mei-Xiang. And the article was included in Organic Chemistry Frontiers in 2017.Reference of 60221-37-6 This article mentions the following:

The practical synthesis and conformational structure of hydrazo-bridged homo calix[4]arenes I (R = Bu, 1-butyl-pentyl, 2-(2-[2-(oxan-2-yloxy)ethoxy]ethoxy)ethyl; X = H, Me) are presented. The step-wise fragment coupling method based on the nucleophilic aromatic substitution reaction of 2,6-dihydrazinylpyridine with 6-alkoxy-2,4-dichlorotriazine e.g., 2-butoxy-4,6-dichlorotriazine afforded effectively hydrazo-linked homo calix[2]pyridine[2]triazines I (R = Bu, 1-butyl-pentyl, 2-(2-[2-(oxan-2-yloxy)ethoxy]ethoxy)ethyl; X = H). The exhaustive methylation of -NHNH- linkages led to lipophilic macrocycles, while the introduction of a THP-protected triglyme moiety on a triazine ring produced a water soluble hydrazo-bridged homo calix[2]pyridine[2]triazine I R = (2-(2-[2-(oxan-2-yloxy)ethoxy]ethoxy)ethyl; X = H). The acquired hydrazo-bridged homo calix[4]arenes I adopted a cone conformational structure with two nitrogen atoms of the hydrazine linkage forming resp. a conjugation system with pyridine and triazine rings. The unique macrocyclic conformation and multidentate binding sites would render hydrazo-bridged homo calix[2]pyridine[2]triazines powerful hosts in mol. recognition and self-assembly. In the experiment, the researchers used many compounds, for example, 2-(2-(2-((Tetrahydro-2H-pyran-2-yl)oxy)ethoxy)ethoxy)ethan-1-ol (cas: 60221-37-6Reference of 60221-37-6).

2-(2-(2-((Tetrahydro-2H-pyran-2-yl)oxy)ethoxy)ethoxy)ethan-1-ol (cas: 60221-37-6) belongs to ethers. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly autoxidize to form hydroperoxides and dialkyl peroxides. If concentrated or heated, these peroxides may explode. To prevent such explosions, ethers should be obtained in small quantities, kept in tightly sealed containers, and used promptly.Reference of 60221-37-6

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Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

A Unified Approach for the Stereoselective Total Synthesis of Pyridone Alkaloids and Their Neuritogenic Activity was written by Jessen, Henning Jacob;Schumacher, Andreas;Shaw, Travis;Pfaltz, Andreas;Gademann, Karl. And the article was included in Angewandte Chemie, International Edition in 2011.Computed Properties of C14H15BO4 This article mentions the following:

The stereoselective total syntheses of the pyridone alkaloids pretenellin B (I), farinosone A (II), militarinone D (III), and the unknown precursor prebassianin B (IV), as well as their resp. enantiomers have been reported. These pyridone polyenes display general neuritogenic activity in the PC-12 cell model. In addition, the previously unknown absolute configuration of the natural products was assigned. In the experiment, the researchers used many compounds, for example, (4-((4-Methoxybenzyl)oxy)phenyl)boronic acid (cas: 156635-90-4Computed Properties of C14H15BO4).

(4-((4-Methoxybenzyl)oxy)phenyl)boronic acid (cas: 156635-90-4) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. At room temperature, ethers are pleasant-smelling colourless liquids. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil.Computed Properties of C14H15BO4

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Sulfoxides as stereochemical controllers in intermolecular Heck reactions was written by Buezo, Nuria Diaz;De la Rosa, Juan Carlos;Priego, Julian;Alonso, Ines;Carretero, Juan Carlos. And the article was included in Chemistry – A European Journal in 2001.Application In Synthesis of 4-Iodo-1-methoxy-2-methylbenzene This article mentions the following:

The study of a variety of substituted sulfoxides as chiral auxiliaries in intermol. Heck reactions of sulfinyldihydrofurans and sulfinylcyclopentenes with different iodoarenes is reported. In the presence of [Pd(OAc)₂]/Ag₂CO₃ and a bidentate phosphine ligand, synthetically useful yields and asym. inductions were obtained. By far the best diastereoselectivities were obtained by the use of the palladium-coordinating o-(N,N-dimethylamino)phenylsulfinyl group. By final removal of the chiral auxiliary, these sulfoxide-stereocontrolled asym. Heck processes were applied to the enantioselective synthesis of 1-aryl-substituted and 1,3-diaryl-substituted dihydrofurans and cyclopentenes. In the experiment, the researchers used many compounds, for example, 4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2Application In Synthesis of 4-Iodo-1-methoxy-2-methylbenzene).

4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2) belongs to ethers. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive. Ethyl ether is an excellent solvent for extractions and for a wide variety of chemical reactions. It is also used as a volatile starting fluid for diesel engines and gasoline engines in cold weather. Dimethyl ether is used as a spray propellant and refrigerant. Methyl t-butyl ether (MTBE) is a gasoline additive that boosts the octane number and reduces the amount of nitrogen-oxide pollutants in the exhaust. The ethers of ethylene glycol are used as solvents and plasticizers.Application In Synthesis of 4-Iodo-1-methoxy-2-methylbenzene

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

2-Substituted-5-nitropyrimidines by the condensation of sodium nitromalonaldehyde with amidines was written by Fanta, Paul E.;Hedman, Edward A.. And the article was included in Journal of the American Chemical Society in 1956.Application of 51488-33-6 This article mentions the following:

p-MeC₆H₄C(:NH)NH₂ (I) (1.86 g.) and 1.57 g. Na[C(NO₂)(CHO)₂] (II) mixed in 25 cc. H₂O at room temperature gave I-II salt, fine white needles, m. 148-50° (from H₂O), which, heated 2 h. at 70° in aqueous Triton B, yielded 5-nitro-2-p-tolylpyrimidine (III), m. 217°. PhC(:NH)NH₂.HCl (IIIa) and II mixed in H₂O at room temperature darkened and resinified on standing and the product was characterized only by conversion to 5-nitro-2-phenylpyrimidine (IV) on heating in aqueous Triton B. IIIa.2H₂O and II.H₂O heated 4 h. with aqueous Triton B at 70° gave 79% IV; IIIa and II heated similarly with aqueous K₂CO₃ gave 66% IV and with aqueous NaOH 42% IV (NH₃ evolved during the reaction); II and IIIa refluxed 4 h. with aqueous NaOH gave no IV but NH₃ was evolved during the reaction and BzOH was isolated from the mixture II and IIIa heated 15 min. at 80° with Ac₂O-pyridine yielded 85% IV; a similar run but without the pyridine gave only 40% IV. II and IIIa refluxed 2 h. with EtOH and NaOEt, or kept 12 h. at 0° with alc. HCl gave no IV. IIIa.2H₂O.HCl (1.94 g.) and 1.57 g. II in 25 cc. H₂O treated with 1 cc. Triton B, heated 4 h. at 65-70°, and refrigerated overnight yielded 1.50 g. IV, pale tan microcrystals, m. 222-3.5°. II (2.8 g.) mixed intimately with 1.8 g. MeC(:NH)NH₂.HCl, treated with a few drops piperidine, heated 1 h. on the steam bath, treated with 1 g. Na₂CO₃, heated 0.5 h., dissolved in a small amount of H₂O, the solution cooled, filtered, and the residue extracted with ligroine gave less than 1% 2-methyl-5-nitropyrimidine, m. 186-7° (from ligroine); a similar run with NaOH in EtOH gave no better yields. II treated with concentrated NH₄OH or with NH₄Cl, NH₄OAc, or AcNH₂ in the presence of Triton B gave an intractable resin. The appropriate nitrile (0.5 mol) and 0.5 mol absolute MeOH treated with a slight excess of dry HCl in 25 cc. absolute Et₂O, and the resulting solid imidic ester HCl salt decomposed with 10% NH₃ in absolute MeOH gave the corresponding amidines which were isolated as their HCl salts and converted by the method described for the preparation of III to the corresponding 2-substituted-5-nitropyrimidines (V); in this manner were prepared the following arylamidine HCl salts and V (aryl group of amidine = 2-substituent of V, m.p. of amidine HCl salt, m.p. and % yield of V given): Ph, 70-3°, 222-3.5°, 79; p-MeC₆H₄, 215-16°, 249-50°, 87; p-MeOC₆H₄, 216-18°, 216-18°, 30; p-BrC₆H₄, 261-3°, 225-7°, 89; p-ClC₆H₄, 240-4°, 170-1.5°, 81; p-FC₆H₄, 209-11°, 154-5°, 71; p-O₂NC₆H₄, 294-5°, 235-7°, 48; p-H₂NO₂SC₆H₄, 207-9°, 268-70°, 41; p-PhC₆H₄, 245-9°, 253-4°, 85; m-O₂NC₆H₄, 238-42°, 133-4°, 79; 3,4-(MeO)₂C₆H₃, 234°, 182-3°, 67; 3-C₅H₄N, 190-4°, 202-3°, 36; PhCH₂, 151-3°, 170°, 77 (picrate, m. 228-30°); 3,4-(MeO)₂C₆H₃CH₂, 153-5°, 235°, 38; PhCH:CH, 68-70°, 219-20°, 81; BzCH₂, -, 210-11°, 70 (free amidine, m. 185-7°). The following aliphatic amidine HCl salts (alkyl group and m.p. given) did not condense with II: Me, 164-6°; Bu, oil (picrate, m. 193-5°); C₁₁H₂₃, 125-7°; MeCH(OH), 162-6°; HOCH₂CH₂, 81-2°. IV (0.20 g.) in 0.40 g. NaOH in 10 cc. H₂O treated with warming and stirring with 1.05 g. Na₂S₂O₄, centrifuged to remove a small amount of brown solid, cooled to 5°, and treated with 2 cc. Ac₂O yielded the 5-AcNH analog of IV, shiny white platelets, m. 208-9° (from 20% aqueous EtOH). IV (2.00 g.) in 200 cc. absolute EtOH hydrogenated 0.5 h. at room temperature and 3 atm. pressure over 0.6 g. 5% Pd-C, the suspension evaporated to dryness in vacuo on the steam bath, the residue extracted with boiling C₆H₆, and the extract cooled yielded 1.50 g. 5-amino-2-phenylpyrimidine (VI), m. 90.5-92°. Similarly was obtained 5-amino-2-(p-tolyl)pyrimidine, 95%, m. 183.5-84°. VI diazotized under various conditions and each reaction mixture tested for the presence of aromatic diazonium salt with an alk. solution of 2-C₁₀H₇OH in no case gave a color. In the experiment, the researchers used many compounds, for example, 3,4-Dimethoxybenzimidamide hydrochloride (cas: 51488-33-6Application of 51488-33-6).

3,4-Dimethoxybenzimidamide hydrochloride (cas: 51488-33-6) belongs to ethers. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides. Ethers feature bent C–O–C linkages. In dimethyl ether, the bond angle is 111° and C–O distances are 141 pm. The barrier to rotation about the C–O bonds is low. The bonding of oxygen in ethers, alcohols, and water is similar. In the language of valence bond theory, the hybridization at oxygen is sp3.Application of 51488-33-6

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem