Pyrimidines

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.1211443-61-6, name is 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide, molecular formula is C14H17ClN4O, molecular weight is 292.76, as common compound, the synthetic route is as follows.SDS of cas: 1211443-61-6

2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-6-carboxamide (500 mg, 1.71 mmol) was suspended in 20 mL of 1,4 – in dioxane,2-Amino-5-nitropyridine (356 mg, 2.56 mmol), Pd(OAc) 2 (9.6 mg, 0.043 mmol),BINAP (53 mg, 0.09 mmol) and Cs2CO3 (834 mg, 2.56 mmol) were applied to argon for 3 times and warmed to 100 C overnight.After cooling to room temperature, the reaction mixture was concentrated under reduced pressure.The crude silica gel column was chromatographed to give 200 mg of desired product 3-7.Yellow solid with a yield of 30%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1211443-61-6, 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide, and friends who are interested can also refer to it.

Reference:
Patent; Nankai University; Xiang Rong; Fan Yan; Li Yongtao; Guo Qingxiang; Huang Zhi; Wang Xin; Zhang Chao; Liu Yanhua; (32 pag.)CN108929324; (2018); A;,
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Synthetic Route of 302964-08-5, 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.302964-08-5, name is 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, molecular formula is C16H13Cl2N5OS, molecular weight is 394.2783, as common compound, the synthetic route is as follows.

Compound I is prepared according to the procedure described in US/2006/0004067A1 (Bang-Chi Chen, et al, published Jan. 05, 2006).

Statistics shows that 302964-08-5 is playing an increasingly important role. we look forward to future research findings about 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/219370; (2007); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 871254-61-4, 2,4-Dichloropyrimidine-5-carbaldehyde, 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, Recommanded Product: 871254-61-4, blongs to pyrimidines compound. Recommanded Product: 871254-61-4

The mixture of 9 (8.8 g, 50.0 mmol) and Et3N (15.2 g, 150.0 mmol)in THF (150 mL) was stirred at 0 C for 10 min under argon. To the solution was added 3-nitrobenzylhydrazine dihydrochloride (11.2 g,55.0 mmol) and then warm to r.t. and stirred for 4 h. The solvent wasremoved in vacuo, and the residue was partitioned between CH2Cl2(50 mL) and H2O (100 mL). The layers were separated, and the aqueouslayer was extracted with CH2Cl2 (2 × 50 mL). The combined organiclayers were dried over anhydrous sodium sulfate, filtered, and concentratedto provide the crude product, which was purified by silica gelcolumn chromatography (eluting with 0-10% MeOH in DCM) to provide10a, white solid, yield 62% (9.0 g, 31.1 mmol). 1H NMR(300 MHz, CDCl3) delta 8.93 (s, 1H), 8.25 (m, 1H), 8.18 (m, 1H), 8.07 (s,1H), 7.71 (d, J = 9 Hz, 1H), 7.53 (t, J = 9 Hz, 1H), 5.71 (s, 2H); MS(ESI) m/z: 290.1 [M+H]+.

The synthetic route of 871254-61-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yin, Yuan; Chen, Cheng-Juan; Yu, Ru-Nan; Shu, Lei; Wang, Zhi-Jian; Zhang, Tian-Tai; Zhang, Da-Yong; Bioorganic Chemistry; vol. 98; (2020);,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 62802-38-4, 5-Bromo-2-fluoropyrimidine, 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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

[Step 1] Production of 2-fluoro-5-(trimethylstannanyl)pyrimidine To 5-bromo-2-fluoropyrimidine (300 mg), hexamethylditin (841 mg) and Pd(PPh3)4 (202 mg) was added 1,4-dioxane (33 mL), and the mixture was stirred under Ar atmosphere at 100C for 10 hours, and stirred at room temperature for 2 days. The solvent of the reaction mixture was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give the title compound (361 mg) as colorless oil.

The synthetic route of 62802-38-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nippon Shinyaku Co., Ltd.; TSUJI, Takashi; SHIRAI, Masaaki; EP2891656; (2015); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 2972-52-3, 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.2972-52-3, name is 2,4-Dichloro-5-pyrimidinecarbonyl chloride, molecular formula is C5HCl3N2O, molecular weight is 211.43, as common compound, the synthetic route is as follows.

Amberlyst A-21 ion exchange resin (1. 8 g) was added to a solution of 2,4- DICHLOROPYRIMIDINE-5-CARBONYL chloride (18.3 g, 86. 6 mmol) in ethyl acetate (400 mL). More ethyl acetate (50 mL) was added and 2,6-dimethylaniline (10.5 g, 10.7 mL, 86. 6 mmol) was added dropwise at room temperature. The reaction mixture was heated at 50 C overnight then cooled and quenched with water and extracted extracted with ethyl acetate (3 x 100 mL). The organic layer was washed with 1 N HC1 (30 mL), 1 M NaOH (30 mL) and brine (30 mL). The organic layer was then dried on sodium sulfate, filtered and concentrated in vacuo. The crude product was washed with dichloromethane (2 X 30 ML) to afford the title compound as a pale yellow solid NMR (400 MHz, CDC13) : 9. 08 (1H, s), 7.71 (1H, s), 7.15-7. 23 (3H, m), 2.32 (6H, s); 13C NMR (400 MHz, CDC13) : 19.12, 127.56, 128. 78, 129.00, 132.75, 135.81, 158. 61,160. 25,162. 23,162. 41; MS: 296 [M+H+]

Statistics shows that 2972-52-3 is playing an increasingly important role. we look forward to future research findings about 2,4-Dichloro-5-pyrimidinecarbonyl chloride.

Reference:
Patent; AMGEN INC.; WO2005/9443; (2005); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 14394-70-8, 2-Chloro-5-methylpyrimidin-4-amine, 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: C5H6ClN3, blongs to pyrimidines compound. Formula: C5H6ClN3

[0126] 2-chloro-5-methyl-pyrimidin-4-ylamine (0.408 g, 2.83 mmol, 1 equiv), 4-Bromo- 1,2-dichloro-benzene (0.704 g, 3.12 mmol, 1.1 equiv), cesium carbonate (2.8 g, 8.49 mmol, 3 equiv), 4,5-bis(diphenylphosrhohino)-9,9-dimethyl xanthene (0.328 g5 0.57 mmol, 0.2 equiv) and tris(dibenzylideneacetone) dipalladium (0.26 g, 0.283 mmol, 0.1 equiv) were combined in 30ml microwave vessel. Reactants were then diluted with 12ml dioxane and microwaved for 25 minutes at 160 0C. Reaction vessel was then spun down, decanted and evaporated to dryness. Resulting solids were diluted with DCM and adsorbed onto silica gel. Chromatography (gradient of 15% ethyl acetate in hexanes up to 80% ethyl acetate in hexanes) afforded the title intermediate 19 as a pale yellow powder (0.366 g, 45% yield). MS (ESI+): 287.97 (M+H), r.t. = 3.12 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14394-70-8, 2-Chloro-5-methylpyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; TARGEGEN, INC.; WO2007/53452; (2007); A1;,
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Pyrimidine – Wikipedia

Reference of 1195768-23-0 , The common heterocyclic compound, 1195768-23-0, name is N-(3-(2-(tert-Butyl)-5-(2-chloropyrimidin-4-yl)thiazol-4-yl)-2-fluorophenyl)-2,6-difluorobenzenesulfonamide, molecular formula is C23H18ClF3N4O2S2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Step D: A/-{3-[5-(2-amino-4-pyhmidinyl)-2-(1 ,1 -dimethylethyl)-1 ,3-thiazol-4-yl]-2- fluorophenyl}-2,6-difluorobenzenesulfonannideIn 1 gal pressure reactor, a mixture of A/-{3-[5-(2-chloro-4-pyrinnidinyl)-2-(1 ,1 – dimethylethyl)-1 ,3-thiazol-4-yl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide (120 g) prepared in accordance with Step C, above, and ammonium hydroxide (28-30%, 2.4 L, 20 vol) was heated in the sealed pressure reactor to 98-103 C and stirred at this temperature for 2 hours. The reaction was cooled slowly to room temperature (20 C) and stirred overnight. The solids were filtered and washed with minimum amount of the mother liquor and dried under vacuum. The solids were added to a mixture of EtOAc (15 vol)/ water (2 vol) and heated to complete dissolution at 60-70 C and the aqueous layer was removed and discarded. The EtOAC layer was charged with water (1 vol) and neutralized with aq. HCI to ~pH 5.4-5.5. and added water (1 vol). The aqueous layer was removed and discarded at 60-70 C. The organic layer was washed with water (1 vol) at 60-70 C and the aqueous layer was removed and discarded. The organic layer was filtered at 60 C and concentrated to 3 volumes. EtOAc (6 vol) was charged into the mixture and heated and stirred at 72 C for 10 min , then cooled to 20C and stirred overnight. EtOAc was removed via vacuum distillation to concentrate the reaction mixture to ~3 volumes. The reaction mixture was maintained at ~65-70C for ~30mins. Product crystals having the same crystal form as those prepared in Example 58b (and preparable by the procedure of Example 58b), above, in heptanes slurry were charged. Heptane (9 vol) was slowly added at 65-70 C. The slurry was stirred at 65-70 C for 2- 3 hours and then cooled slowly to 0-5C. The product was filtered, washed withEtOAc/heptane (3/1 v/v, 4 vol) and dried at 45C under vacuum to obtain A/-{3-[5-(2- amino-4-pyrimidinyl)-2-(1 ,1 -dimethylethyl)-1 ,3-thiazol-4-yl]-2-fluorophenyl}-2,6- difluorobenzenesulfonamide (102.3 g, 88%).

The synthetic route of 1195768-23-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; DUMBLE, Melissa; KUMAR, Rakesh; LAQUERRE, Sylvie; LEBOWITZ, Peter; WO2011/47238; (2011); A1;,
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Reference of 934524-10-4, Adding some certain compound to certain chemical reactions, such as: 934524-10-4, name is 2,4-Dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine,molecular formula is C13H9Cl2N3O2S, 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 934524-10-4.

To a stirred solution of 4-methoxyphenol (87 mg, 0.70 mmol) in DMF (10 mL) was added Cs2CO3 (229 mg, 0.70 mmol). After 10 min, 2,4-dichloro-N-tosylpyrrolopyrimidine 3 (200 mg, 0.58 mmol) was added and the mixture was stirred at room temperature for 30 min. The reaction mixture was diluted with H2O (40 mL) and extracted with EtOAc (2 * 30 mL). The combined organic extracts were washed with brine (6 * 25 mL), dried, filtered and the solvent was removed in vacuo to give a grey residue. The residue was purified by flash chromatography (20% EtOAc/Hexanes) and recrystallised from n-PrOH to give 5c (150 mg, 51%) as a white solid; mp 161-164 C; deltaH (CDCl3): 8.10 (2H, d, J 8.0 Hz), 7.55 (1H, d, J 4.0 Hz), 7.32 (2H, d, J 8.0 Hz), 7.06 (2H, d, J 9.0 Hz), 6.90 (2H, d, J 9.0 Hz), 6.41 (1H, d, J 4.0 Hz), 3.81 (3H, s), 2.40 (3H, s); deltaC (CDCl3): 163.0, 157.5, 154.1, 153.2, 146.2, 145.5, 134.3, 129.9, 128.7, 124.9, 122.2, 114.7, 106.6, 102.3, 55.6, 21.7; m/z (ESI): 430.0 (M[35Cl]H+), 432.0 (M[37Cl]H+); HRMS (ESI): M[35Cl]H+, found 430.0636. C20H17ClN3O4S+ requires 430.0623.

According to the analysis of related databases, 934524-10-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; O’Brien, Nathan J.; Brzozowski, Martin; Buskes, Melissa J.; Deady, Leslie W.; Abbott, Belinda M.; Bioorganic and Medicinal Chemistry; vol. 22; 15; (2014); p. 3879 – 3886;,
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Pyrimidine – Wikipedia

Reference of 18740-38-0, 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.18740-38-0, name is Thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione, molecular formula is C6H4N2O2S, molecular weight is 168.1732, as common compound, the synthetic route is as follows.

To a solution of 1H-thieno[2,3-d]pyrimidine-2,4-dione (62) (92.8 mg, 0.552 mmol) in toluene (1 mL) were added N,N-dimethylaniline (0.140 mL, 1.10 mmol) and phosphoryl chloride (0.280 mL, 3.00 mmol). The reaction mixture was warmed to 100 C and stirred for 3 h. After cooling to room temperature, H2O was added to the reaction mixture and the mixture was extracted with CHCl3. The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo to give 2,4-dichlorothieno[2,3-d]pyrimidine (63). This compound was used for the next reaction without further purification.To a solution of 63 in DMF (4 mL) was added ethyl 2-(4-aminophenyl)acetate (95.2 mg, 0.531 mmol) and the reaction mixture was stirred at 65 C for 2.5 h. After cooling, H2O was added to the reaction mixture and the mixture was extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was chromatographed (EtOAc/hexane = 0% to 100%) to give the title compound (85.9 mg, 0.247 mmol, 45%) as a colorless solid. 1H NMR (CDCl 3) delta: 1.28 (3H, t, J = 7.4 Hz), 3.64 (2H, s), 4.18 (2H, q, J = 7.4 Hz), 7.03 (1H, d, J = 5.7 Hz), 7.21 (1H, s), 7.29 (1H, d, J = 5.7 Hz), 7.32 (2H, d, J = 8.6 Hz), 7.56 (2H, d, J = 8.6 Hz).

Statistics shows that 18740-38-0 is playing an increasingly important role. we look forward to future research findings about Thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione.

Reference:
Article; Goto, Taiji; Shiina, Akiko; Yoshino, Toshiharu; Mizukami, Kiyoshi; Hirahara, Kazuki; Suzuki, Osamu; Sogawa, Yoshitaka; Takahashi, Tomoko; Mikkaichi, Tsuyoshi; Nakao, Naoki; Takahashi, Mizuki; Hasegawa, Masashi; Sasaki, Shigeki; Bioorganic and Medicinal Chemistry Letters; vol. 23; 11; (2013); p. 3325 – 3328;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 18592-13-7, 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. 18592-13-7, name is 6-(Chloromethyl)pyrimidine-2,4(1H,3H)-dione. A new synthetic method of this compound is introduced below.

6-[(4-Fluorophenyl)sulfanylmethyl]-1H-pyrimidine-2,4-dione DBU (4.02 mL, 26.91 mmol) was added to 4-fluorobenzenethiol (3.45 g, 26.91 mmol), in DMF (90 mL) at RT. The resulting solution was stirred at 20 C. for 15 minutes. 6-(Chloromethyl)-1H-pyrimidine-2,4-dione (2.88 g, 17.94 mmol) was then added and the reaction stirred for 4 hours. The reaction mixture was concentrated and diluted with DCM (100 mL), and washed with water (100 mL). The aqueous layer was acidified with 2M hydrochloric acid to give a white solid which was filtered and washed with water then dried under vacuum to give desired product (2.5 g). NMR Spectrum: 1H NMR (400.132 MHz, DMSO-d6) delta 3.80 (2H, s), 5.20 (1H, s), 7.18-7.23 (2H, m), 7.45-7.49 (2H, m), 10.90 (1H, s), 10.93 (1H, s)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,18592-13-7, its application will become more common.

Reference:
Patent; AstraZeneca AB; US2009/18134; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia