Pyrimidines

Application of 330786-24-8, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 330786-24-8, name is 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

The 3- (4-phenoxyphenyl) -1H-pyrazolo [3,4-d]pyrimidin-4-amine(compound 2a)(2.12g,7mmol), 3-hydroxypiperidine-1- tert-Butyl formate(1.55g,7.7mmol), Triphenylphosphine(2.75g,10.5mmol)and Azobisisobutyronitrile (2.12g,10.5mmol) dissolved in THF (250ml), keep thereaction at room temperature for 12h(TLC thin layer chromatography monitoringreaction is complete or not). After the completion of the reaction , solventwas recovered under reduced pressure. into the remaining reaction mixture added100 ethyl acetate, organic layer was extracted three times with Saturatedsodium carbonate solution 100ml*3, organic phases were combined, washed oncewith saturated sodium chloride and dried over anhydrous sodium sulfate. The solvent was recovered under reducedpressure to give 1.12 g of a brown solid in 33% yield.

According to the analysis of related databases, 330786-24-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HANGZHOU HERTZ PHARMACEUTICAL CO LTD; ZHOU, XINGLU; HAN, LING; GE, ZHEN; LIU, XINGGUO; LUO, WENHUA; LIU, WENHUA; (27 pag.)CN104844609; (2016); B;,
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Application of 583878-42-6, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.583878-42-6, name is Ethyl 4-chloro-6-methyl-2-(methylthio)pyrimidine-5-carboxylate, molecular formula is C9H11ClN2O2S, molecular weight is 246.71, as common compound, the synthetic route is as follows.

Intermediate 1 1Ethyl 4-({3-r3-({r(1 , 1-dimethylethyl)oxylcarbonyl}amino)propyllphenyl}amino)-6-methyl-2-(methylthio)-5-pyrimidinecarboxylateTo a solution of 1 ,1-dimethylethyl [3-(3-aminophenyl)propyl]carbamate (390 mg, 1.558 mmol) in DMF (5 ml.) were added ethyl 4-chloro-6-methyl-2-(methylthio)-5- pyrimidinecarboxylate (307 mg, 1.246 mmol) and DIEA (0.298 ml_, 1.714 mmol), and the reaction mixture was stirred at 75 0C overnight. The reaction was then concentrated and the residue was purified using column chromatography (silica gel, 0% to 50% EtOAc gradient in hexane) to afford the product (210 mg, 29% yield). MS: M(C23H32N4O4S) = 460.59, (M+H)+ = 461.6 1 H NMR (400 MHz, CD3OD) delta ppm 1.44 – 1.47 (m, 12 H), 1.77 – 1.85 (m, 3 H), 2.52 (s, 3 H), 2.62 (s, 3 H), 2.65 (d, J = 8.6 Hz, 2 H), 3.09 (t, J = 7.0 Hz, 2 H), 4.45 (q, J = 7.2 Hz, 2 H), 4.64 (br. s., 1 H), 7.01 (d, J = 7.6 Hz, 1 H), 7.28 (t, J = 7.8 Hz, 1 H), 7.42 (d, J = 1.3 Hz, 1 H), 7.55 – 7.58 (m, 1 H).

The chemical industry reduces the impact on the environment during synthesis 583878-42-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; ATKINSON, Francis, Louis; AXTEN, Jeffrey, Michael; CICHY-KNIGHT, Maria; MOORE, Michael, Lee; PATEI, Vipulkumar, Kantibhai; TIAN, Xinrong; WELLAWAY, Christopher, Roland; DUNN, Allison, K.; WO2010/19637; (2010); A1;,
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The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 13223-25-1, name is 2-Chloro-4,6-dimethoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 13223-25-1

Example 5 Synthesis of 3-(4,6-dimethoxy-2-pyrimidinyloxy)-2-pyridinecarboxaldehyde diethylacetal (Compound No. 3) Step (d)] Sodium hydride (7.0 g) was added under stirring to 300 ml of dimethylimidazolidinone, followed by the gradual addition of 37.5 g of 3-hydroxy-2-pyridinecarboxaldehyde diethylacetal at room temperature. Heat was evolved with bubbling so that the temperature of the mixture arose to 55 C. After the mixture was heated for 1 hour at 90-95 C., 31.6 g of 2-chloro-4,6-dimethoxypyrimidine were added. The reaction mixture was heated at 100-120 C. for 8 hours so that the reaction was brought to completion. The reaction mixture was cooled to room temperature, added with 500 ml of water, and then extracted three times with 700 ml portions of ethyl acetate. The organic layers were combined, washed with water and then dried over anhydrous sodium sulfate. The solvent was then distilled out, whereby 87.4 g of an oily residue were obtained. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate=1:1) so that 54.6 g of 3-(4,6-dimethoxy-2-pyrimidinyloxy)-2-pyridinecarboxaldehyde diethylacetate were obtained (yield: 90%).

With the rapid development of chemical substances, we look forward to future research findings about 13223-25-1.

Reference:
Patent; Mitsui Toatsu Chemicals Incorporated; US5129937; (1992); A;,
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Electric Literature of 444731-75-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 444731-75-3, name is N-(2-Chloropyrimidin-4-yl)-N,2,3-trimethyl-2H-indazol-6-amine, molecular formula is C14H14ClN5, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of Intermediate Example 4 (200 mg, 0.695 mmol) and 5-amino-2- methylbenzenesulfonamide (129.4 mg, 0.695 mmol) in isopropanol (6 ml) was added 4 drops of cone. HCI. The mixture was heated to reflux overnight. The mixture was cooled to rt and diluted with ether (6 ml). Precipitate was collected via filtration and washed with ether. The hydrochloride salt of 5-({4-[(2,3-dimethyl-2H-indazol-6- yl)(methyl)amino]-pyrimidin-2-yl}amino)-2-methylbenzenesulfonamide was isolated as an off-white solid. 1H NMR (400 MHz, d6DMSO+NaHCO3) delta 9.50 (br s, 1 H), 8.55 (br s, 1 H), 7.81 (d, J = 6.2 Hz, 1 H), 7.75 (d, J = 8.7 Hz, 1 H), 7.69 (m, 1 H), 7.43 (s, 1 H), 7.23 (s, 2H), 7.15 (d, J = 8.4 Hz, 1 H), 6.86 (m, 1 H), 5.74 (d, J = 6.1 Hz, 1 H), 4.04 (s, 3H), 3.48 (s, 3H), 2.61 (s, 3H), 2.48 (s, 3H). MS (ES+, m/z) 438 (M+H).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 444731-75-3, N-(2-Chloropyrimidin-4-yl)-N,2,3-trimethyl-2H-indazol-6-amine.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/20564; (2006); A1;,
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With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.205672-25-9, name is 4-Amino-5-bromo-2-chloropyrimidine, molecular formula is C4H3BrClN3, molecular weight is 208.44, as common compound, the synthetic route is as follows.Computed Properties of C4H3BrClN3

Synthesis of 2-Chloro-5- (2-ethoxyvinyl)-pyrimidin-4-ylamine (2):; A 500 mL round bottomed flask is charged with 5-bromo-2-chloropyrimidin-4-ylamine (1) (lOg, 48 mmol), tetrakis (triphenylphosphine) palladium (0) (2.8g, 2.5 mmol), and toluene (200 mL). Tributyl- (2-ethoxyvinyl)-stannane (22g, 60 mmol) is added and the reaction heated to 110C with stirring for approximately 15 hours. After cooling to room temperature, the solution is diluted with 100 mL ethyl acetate and washed with water and brine. The organic extract is dried over Na2S04, filtered, and concentrated under reduced pressure. Purification by column chromatography (Si02, Hexane: Ethyl acetate/5: 1) provides 2 (4.4 g, 46%) as a yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,205672-25-9, 4-Amino-5-bromo-2-chloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; IRM LLC; WO2005/80393; (2005); A1;,
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Synthetic Route of 25193-95-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 25193-95-7, name is 5-(Hydroxymethyl)pyrimidine, molecular formula is C5H6N2O, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Into 2 g of N,N-dimethylformamide were dissolved 219 mg of 5-chloro-3-benzylthio-1,2,4-thiadiazole and 200 mg of 5-pyrimidylmethyl alcohol, 44 mg of sodium hydride (60% in oil) was added thereto under ice-cooling, and the reaction mixture was stirred for 30 minutes. After stirring for 5 hours at room temperature, the reaction mixture was added to saturated sodium chloride aqueous solution, and extracted with t-butyl methyl ether. The organic layer was concentrated, and the residue obtained was subjected to silica gel column chromatography to give 130 mg of 5-(5-pyrimidylmethyloxy)-3-benzylthio-1,2,4-thiadiazole (hereinafter, referred to as the present compound (38)). [] 1H-NMR: 9.25 (s, 1H), 8.86 (s, 2H), 7.43-7.24 (m, 5H), 5.53 (s, 2H), 4.41 (s, 2H)

According to the analysis of related databases, 25193-95-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP1475374; (2004); A1;,
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Reference of 4316-97-6, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.4316-97-6, name is 4,6-Dichloro-5-methylpyrimidine, molecular formula is C5H4Cl2N2, molecular weight is 163.01, as common compound, the synthetic route is as follows.

1-Methyl-1 ,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole bis-hydrochloride salt (2.00 g,10.2 mmol) and 4,6-dichloro-5-methylpyrimidine (1.66 g, 10.2 mmol) were suspended tetrahydrofuran (51 ml.) at room temperature. To this was added triethylamine (4.41 ml_, 31.6 mmol), which caused cloudiness in the mixture and led to a brown solid sticking to the flask walls. This mixture was stirred at room temperature for 4 hours and then heated 50 degrees Celsius for an additional 19 hours. The reaction mixture was cooled to room temperature and diluted with water (100 ml_). This mixture was extracted with ethyl acetate (3 x 100 ml_). The organic extracts were pooled, washed with brine, dried over sodium sulfate, and filtered. The filtrate was reduced to dryness under vacuum to yield the title compound as a light brown solid (1 .95 g, 78%), which was used in the next step without further purification.1 H NMR (500 MHz, deuterochloroform) delta 2.54 (s, 3 H) 3.88 (s, 3 H) 4.90 (app. d, J=3.66 Hz, 4 H) 7.28 (s, 1 H) 8.29 (s, 1 H).

The chemical industry reduces the impact on the environment during synthesis 4316-97-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PFIZER INC.; MASCITTI, Vincent; MCCLURE, Kim Francis; MUNCHHOF, Michael John; ROBINSON, Ralph Pelton, Jr.; WO2012/69948; (2012); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 51940-64-8, name is Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate. A new synthetic method of this compound is introduced below., category: pyrimidines

a) (S)-Ethyl 2-chloro-4-(1 -(5-fluoropyridin-2-yl)ethylamino)pyrimidine-5- carboxylateA solution of ethyl 2,4-dichloropyrimidine-5-carboxylate (prepared as described in WO2009/131687, 0.29 g, 1.31 mmol), (S)-1 -(5-fluoropyridin-2-yl)ethanamine hydrochloride (prepared as described in WO2006/1231 13, 0.28 g, 1.59 mmol) and diisopropylethylamine (0.69 ml_, 3.96 mmol) in acetonitrile (3 mL) was stirred overnight at ambient temperature. Water was then added and the reaction mixture was extracted with diethyl ether. The organic phase was washed with water and brine, dried (MgS04), filtered and the solvents evaporated under reduced pressure to yield the title compound (0.49 g, 85%) as an oil.LRMS (m/z): 325 (M+1 )+.1H-NMR delta (CDCIs): 1 .41 (t, 3H), 1 .58 (d, 3H), 4.39 (q, 2H), 5.42-5.55 (m, 1 H),7.31 (dd, 1 H), 7.39 (dd, 1 H), 8.49 (d, 1 H), 8.69 (s, 1 H), 9.37 (d, 1 H

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 51940-64-8, Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate.

Reference:
Patent; ALMIRALL, S.A.; EASTWOOD, Paul Robert; BACH TANA, Jordi; PAGES SANTACANA, Lluis Miquel; WO2013/17461; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 20781-06-0, 2,4-Diaminopyrimidine-5-carboxaldehyde, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Formula: C5H6N4O, blongs to pyrimidines compound. Formula: C5H6N4O

General procedure: Appropriate substituted benzoyl hydrazine 4 (1 equiv) was added to a solution of intermediate 2 (1mmol) in ethanol (10mL). The reaction mixture was stirred for 3h at reflux under the condition of the presence of acetic acid as catalyzer, then poured into cold water and the resulting solid was collected by filtrated, washed with EtOH (10mL), and dried in the atmospheric pressure to give the desired title compounds A, B, and C.

The synthetic route of 20781-06-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; He, Haifeng; Xia, Hongying; Xia, Qin; Ren, Yanliang; He, Hongwu; Bioorganic and Medicinal Chemistry; vol. 25; 20; (2017); p. 5652 – 5661;,
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Adding a certain compound to certain chemical reactions, such as: 99469-85-9, 4,5-Dichloro-2-(methylthio)pyrimidine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Safety of 4,5-Dichloro-2-(methylthio)pyrimidine, blongs to pyrimidines compound. Safety of 4,5-Dichloro-2-(methylthio)pyrimidine

Compound 51. To a mixture of compound 49 (976 mg, 5.13 mmol, 2 eq.), compound 50 (0.5 g, 2.56 mmol, 1 eq.) , Pd(PPh3)2Cl2 (360 mg, 512 mumol, 0.2 eq.), and CuI (244 mg, 1.28 mmol, 0.5 eq.) in THF (10 mL) was added TBAF (1 M, 2.56 mL, 1 eq.) in one portion at 0 C under N2. The reaction mixture was stirred at 60 C under N2 for 10 h. The mixture was partitioned between H2O(100 mL) and EtOAc(200 mL). The combined organic phase were washed with brine (200 mL), dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, PE/EtOAc: 1/0 to 50 /1) and prep- TLC (PE/EtOAc: 20:1) to afford compound 51 (0.3 g, 1.26 mmol, 49% yield) as a brown oil. 1H NMR (CDCl3, 400 MHz) delta 8.47 (s, 1H), 2.61 (d, J = 5.9 Hz, 2H), 2.56 (s, 3H), 1.13-1.03 (m, 1H), 0.61-0.52 (m, 2H), 0.36 (q, J = 4.9 Hz, 2H).

The synthetic route of 99469-85-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM LTD.; SNIR-ALKALAY, Irit; VACCA, Joseph; BEN-NERIAH, Yinon; (238 pag.)WO2019/155468; (2019); A1;,
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