Pyrimidines

Application of 372118-67-7 ,Some common heterocyclic compound, 372118-67-7, molecular formula is C5H8ClN3, 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.

Tosyl chloride (254 mg, 1.33 mmol), K2CO3 (538 mg, 3.9 mmol) and compound 21 (500 mg, 1.33 mmol) were added to acetonitrile (10 mL) and stirred at room temperature overnight. Compound 23 (194 mg, 1.33 mmol) was added to the prepared mixed anhydride solution, stirred at room temperature for 20 minutes, and then detected by TLC. The reaction of the starting material was completed. The mixture was diluted with water and washed with ethyl acetate. The aqueous phase was extracted twice more with ethyl acetate. The combined organic phases were dried over anhydrous sodium sulfate and concentrated to give compound 24 (601 mg, 95% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,372118-67-7, its application will become more common.

Reference:
Patent; Anrun Pharmaceutical (Suzhou) Co., Ltd.; Hong Jian; Xu Xin; Liu Guobin; Liu Huahui; (14 pag.)CN104710411; (2017); B;,
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Pyrimidine – Wikipedia

Application of 4316-97-6, 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. 4316-97-6, name is 4,6-Dichloro-5-methylpyrimidine, molecular formula is C5H4Cl2N2, 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.

Description 95; 6-Chloro-5-methyl-N- [4-trifluoromethvlphenyl] pyrimidin-4- amine; A mixture of 4, 6-dichloro-5-methylpyrimidine (1.0 g, 6.15 mmol) and 4- aminobenzotrifluoride (0.77 ml, 6.15 mmol) in ethanol (12 ml) was heated at 150C for 15 min in a microwave reactor (Personal Chemistry-Emrys Optimizer). The solid which had formed was removed by filtration and dried to give the title compound (950 mg, 53%). 1H NMR (400 MHz, CDCl3) 2.36 (3 H, s), 6.70 (2 H, br s), 7.61 (2 H, d, J8.6), 7.73 (2 H, d, J8.6), 8.44 (1 H, s).

According to the analysis of related databases, 4316-97-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2005/47279; (2005); 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.954220-98-5, name is 2,4-Dichloro-5-fluoro-6-methylpyrimidine, molecular formula is C5H3Cl2FN2, molecular weight is 181, as common compound, the synthetic route is as follows.Formula: C5H3Cl2FN2

Preparation of compound 8: compound 6 (0.62 g, 3.43 mmol), 7 (0.67 g, 3.43 mmol 1) and triethylamine (1.14 g, 13.02 mmol) were dissolved in a mixed solvent of 15 mL of tetrahydrofuran and 0.8 mL of ethanol, and heated under reflux for 5 hours.After the reaction is finished, spin dry,The crude product was subjected to column chromatography to give 0.46 g of Compound 8. Yield: 32.2%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,954220-98-5, 2,4-Dichloro-5-fluoro-6-methylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Yinxingshu Pharmaceutical (Suzhou) Co., Ltd.; Chen Li; Shao Qing; Jiang Tao; Wu Jin; (20 pag.)CN109384783; (2019); A;,
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Pyrimidine – Wikipedia

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1211443-61-6, name is 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 1211443-61-6

General procedure: To a suspension of 2-chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (5) (586 mg, 2 mmol) in 20 mL 1,4-dioxane were added compound 3a-f, 3i-u(2 mmol), Pd(OAc)2 (11 mg, 0.05 mmol), BINAP (62 mg, 0.1 mmol) and Cs2CO3 (978 mg, 3 mmol) and the flask was purged with Ar. Then the flask was sealed and the mixture was heated for 12 h at 100. The reaction was cooled to rt, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 4a-f, 4i-o, 4r-u.

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, 1211443-61-6, 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide.

Reference:
Article; Li, Yongtao; Guo, Qingxiang; Zhang, Chao; Huang, Zhi; Wang, Tianqi; Wang, Xin; Wang, Xiang; Xu, Guangwei; Liu, Yanhua; Yang, Shengyong; Fan, Yan; Xiang, Rong; Bioorganic and Medicinal Chemistry Letters; vol. 27; 15; (2017); p. 3231 – 3237;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 22536-66-9, 2-Chloropyrimidine-4-carboxamide, 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, 22536-66-9, blongs to pyrimidines compound. name: 2-Chloropyrimidine-4-carboxamide

General procedure: To a suspension of (S)-(5 -(5 -fluoropyridin-3 -yl)-4,5 -dihydro- 1H-pyrazol- 1 -yl)(pipendin-4- yl)methanone, 1R-(-)-camphor-10-sulphonic acid salt (500 mg, 0.983 mmol) in MeCN (10 mL) was added 6-chloropynmindine-4-carboxaminde (155 mg, 0.98 mmol) and DIPEA (0.429 mL, 2.46 mmol). The reaction was sealed and stirred at 120 C for 2 h. The reaction minxturewas evaporated in vacuo. The residue was purified by normal phase column chromatography (DCminMeOH 100/0 to 95/5). The appropriate fractions were combined, concentrated in vacuo, and recrystallized from MeCN to afford (S)-6-(4-(5-(5-fluoropyndin-3-yl)-4,5- dihydro- 1H-pyrazole- 1 -carbonyl)pipendin- 1 -yl)pynmindine-4-carboxaminde (200 mg, 0.503 mmol, purity: 100 %, recovery: 51 %) as a white powder. LCMS (m/z) 398 (M+H),retention time: 1.52 min LC/MS Method 1. ?H NMR (400 MHz, DMSO-d6) delta ppm 8.54 (s,1H), 8.47 (d, J=2.6 Hz, 1H), 8.29 (s, 1H), 8.05 (s, 1H), 7.74 (s, 1H), 7.48 (dd, J=9.8, 1.8 Hz,1H), 7.30 (s, 2H), 5.41 (dd, J=12.2, 5.2 Hz, 1H), 4.45 (m, 2H), 3.53 (ddd, J 19.0, 12.1, 1.1Hz, 1H), 3.41 (m, 1H), 3.09 (m, 2H), 2.84 (dd, J19.0, 5.2, 1.5 Hz, 1H), 1.91 (d, J12.0 Hz,1H), 1.82 (d, J=12.2 Hz, 1H), 1.47 (sextuplet of d, J12.5, 3.6 Hz, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22536-66-9, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DAUGAN, Alain Claude-Marie; DONCHE, Frederic G.; FAUCHER, Nicolas Eric; GEORGE, Nicolas S.; (243 pag.)WO2018/92089; (2018); A1;,
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Pyrimidine – Wikipedia

Application of 939986-65-9 , The common heterocyclic compound, 939986-65-9, name is 6-Chloropyrimidine-4-carbonitrile, molecular formula is C5H2ClN3, 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.

To a suspension of (S)-(5 -(3,5 -difluorophenyl)-4,5-dihydro- 1H-pyrazol- 1 -yl)(piperidin-4- yl)methanone, 1R-(-)-camphor-10-sulphonic acid salt (300 mg, 0.57 mmol) in MeCN (30mL) was added 6-chloropyrimindine-4-carbonitrile (80 mg, 0.57 mmol) and DIPEA (0.25 mL,1.43 mmol) The vessel was sealed and heated at 80C for 2 h. The reaction minxture was evaporated in vacuo. This residue was purified by normal phase column chromatography [CyHI(EtOAc/EtOH 3:1) 100/0 to 70/301. A trituration into iPr2O afforded, after filtration, (S)-6-(4-(5 -(3 ,5-difluorophenyl)-4,5 -dihydro- 1H-pyrazole- 1 -carbonyl)piperidin- 1-yl)pyrimindine-4-carbonitrile (130 mg, 0.33 mmol, purity: 100 %, recovery: 58 %) as a light yellow powder. LCMS (m/z) 397 (M+H), retention time: 2.48 min LC/MS Method 1. ?H NMR (400 min-Tz, DMSO-d6) delta ppm 8.54 (s, 1H), 7.57 (s, 1H), 7.26 (s, 1H), 7.12 (tt, J9.4, 2.1 Hz, 1H), 6.84 (d, J=6.5 Hz, 2H), 5.34 (dd, J=12.0, 4.9 Hz, 1H), 4.47 (br.s, 2H), 3.49 (ddd, J=19.0, 12.0, 1.0 Hz, 1H), 3.43 (tt, J=11.4, 3.7 Hz, 1H), 3.13 (brs, 2H), 2.75 (ddd, J19.2,4.9, 1.5 Hz, 1H), 1.95 (d, J=12.7 Hz, 1H), 1.81 (d, J=12.7 Hz, 1H), 1.48 (m, 2H).

The synthetic route of 939986-65-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DAUGAN, Alain Claude-Marie; DONCHE, Frederic G.; FAUCHER, Nicolas Eric; GEORGE, Nicolas S.; (243 pag.)WO2018/92089; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 14080-59-2, name is 4-Chlorothieno[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H3ClN2S

General procedure: alpha,beta-unsaturated tosylhydrazones 1 (0.11 mmol, 1.1 equiv), heteroaryl chlorides 2 (0.1 mmol, 1 equiv), Cs2CO3 (0.25 mmol, 2.5 equiv) and MeCN (1 mL) were added to a tube. The mixture was stirred at 60 C until the heteroaryl chlorides was completely disappeared for 4-8h. After cooling to room temperature, the mixture was quenched with NH4Cl (2 mL, saturated aqueous solution) and extracted with CH2Cl2 (3 ¡Á 2 mL). The combined organic phases were dried over Na2SO4 and solvents removed in vacuo. The residue was purified by flash column chromatography on silica gel with ethyl acetate/petroleum ether (1:10-1:4, V/V) as the eluent, affording the desired product 3 and 4.

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, 14080-59-2, 4-Chlorothieno[2,3-d]pyrimidine.

Reference:
Article; Zeng, Lin; Guo, Xiao-Qiang; Yang, Zai-Jun; Gan, Ya; Chen, Lian-Mei; Kang, Tai-Ran; Tetrahedron Letters; vol. 60; 33; (2019);,
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Adding a certain compound to certain chemical reactions, such as: 3438-46-8, 4-Methylpyrimidine, 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, Quality Control of 4-Methylpyrimidine, blongs to pyrimidines compound. Quality Control of 4-Methylpyrimidine

General procedure: Methyldiazine derivative (1mmol) and compound 3 (1.1equiv per methyl group) were dissolved in THF (20mL). tBuOK (1.5equiv per methyl group) was slowly added at room temperature. The solution, which immediately turned brown, was then refluxed overnight. After cooling, water was added, THF was evaporated and the mixture extracted with CH2Cl2, dried over MgSO4 and the solvent removed under vacuum.

The synthetic route of 3438-46-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Achelle, Sylvain; Kahlal, Samia; Saillard, Jean-Yves; Cabon, Nolwenn; Caro, Bertrand; Robin-Le Guen, Francoise; Tetrahedron; vol. 70; 17; (2014); p. 2804 – 2815;,
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Synthetic Route of 105806-13-1, 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.105806-13-1, name is 4,6-Dichloro-5-fluoro-2-methylpyrimidine, molecular formula is C5H3Cl2FN2, molecular weight is 181, as common compound, the synthetic route is as follows.

Part C: 4-Chloro-6-[(3R)-3,4-dimethyl-1-piperazinyl]-5-fluoro-2-methylpyrimidine. To a solution of 4,6-dichloro-5-fluoro-2-methylpyrimidine (0.181 g, 1.0 mmol) and (2R)- 1 ,2-dimethylpiperazine dihydrochloride (0.189 g, 1.0 mmol) in THF (10 mL) was added triethylamine (0.42 mL, 3.0 mmol). MeOH (1 mL) was added to improve solubility. Reaction left to stir overnight. The solvent was removed in vacuo, and THF and ether were added to the resulting residue, which was washed with water. The organics were dried (Na2SO4) and concentrated in vacuo to provide 4-chloro-6-[(3R)-3,4-dimethyl-1- piperazinyl]-5-fluoro-2-methylpyrimidine as a yellow oil (0.242 g, 94%). LCMS: (M+H)+ = 259.3.

The chemical industry reduces the impact on the environment during synthesis 105806-13-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/61879; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 739364-95-5, 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. 739364-95-5, name is 2-Methylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid. A new synthetic method of this compound is introduced below.

(Intermediate Example 113) 2-Methylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid (4-amino-4-methylpentyl)amide 2-Methylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid (177 mg) was suspended in tetrahydrofuran (5 ml), and N,N-dimethylformamide (1 drop) was added thereto. Oxalyl chloride (100 mul) was added thereto with ice cooling, and the mixture was stirred for 30 minutes at room temperature. The mixture was cooled again on ice, and 4-methyl-1,4-pentane< >diamine (116 mul) and triethylamine (0.21 ml) were added thereto and stirred overnight at room temperature. By adding water and 2 N hydrochloric acid, the reaction mixture was acidified, followed by washing with chloroform. The aqueous phase was alkalinized by 5 N sodium hydroxide solution, extracted with chloroform, and the extract was dried over sodium sulfate anhydrous. The product was concentrated under reduced pressure to give the title compound (151 mg, Y.: 55%) as pale yellow crystals. 1H NMR; (CDCl3) delta (ppm): 1.1 (6H, s), 1.7 (4H, m), 2.5 (3H, s), 3.4 (2H, dd), 6.5 (1H, s), 8.4 (1H, brs), 8.7 (1H, d), 9.1 (1H, d). ESI/MS (m/z): 276 (M+H)+, 274 (M-H)-.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,739364-95-5, its application will become more common.

Reference:
Patent; SANWA KAGAKU KENKYUSHO CO., LTD.; EP1595866; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia