Pyrimidines

Reference of 1558-17-4 ,Some common heterocyclic compound, 1558-17-4, molecular formula is C6H8N2, 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.

General procedure: Preparation of 1a’-3f’ and 1g-5g. A mixture of pyrimidines (2.00 mmol) and benzaldehydes (4.00 mmol) in 5 N NaOH solution (20 mL) containing tetrabutylammonium hydrogen sulfate (0.10 g, 0.29 mmol) was refluxed. After cooling, the precipitates were filtered off. The products were purified by recrystallization from EtOAc. Otherwise, the mixture was extracted with CH2Cl2. Then, the organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography to give the products.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1558-17-4, its application will become more common.

Reference:
Article; Lee, Yun Suk; Kim, Hye Yun; Kim, Youngsoo; Seo, Jae Hong; Roh, Eun Joo; Han, Hogyu; Shin, Kye Jung; Bioorganic and Medicinal Chemistry; vol. 20; 16; (2012); p. 4921 – 4935;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 444731-75-3, 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.444731-75-3, name is N-(2-Chloropyrimidin-4-yl)-N,2,3-trimethyl-2H-indazol-6-amine, molecular formula is C14H14ClN5, molecular weight is 287.75, as common compound, the synthetic route is as follows.

Example 69 5-({4-[(2,3-dimethyl-2H-indazol-6-yl)(methyl)amino]pyrimidin-2-yl}amino)-2-methylbenzenesulfonamide To a solution of Intermediate Example 13 (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 conc. HCl. 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. HCl 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, 1H), 8.55 (br s, 1H), 7.81 (d, J = 6.2 Hz, 1H), 7.75 (d, J = 8.7 Hz, 1H), 7.69 (m, 1H), 7.43 (s, 1H), 7.23 (s, 2H), 7.15 (d, J = 8.4 Hz, 1H), 6.86 (m, 1H), 5.74 (d, J = 6.1 Hz, 1H), 4.04 (s, 3H), 3.48 (s, 3H), 2.61 (s, 3H), 2.48 (s, 3H). MS (ES+, m/z) 438 (M+H).

Statistics shows that 444731-75-3 is playing an increasingly important role. we look forward to future research findings about N-(2-Chloropyrimidin-4-yl)-N,2,3-trimethyl-2H-indazol-6-amine.

Reference:
Patent; Novartis AG; Boloor, Amogh; Cheung, Mui; Davis, Ronda; Harris, Philip Anthony; Hinkle, Kevin; Mook, Robert Anthony Jr; Stafford, Jeffery Alan; Veal, James Martin; EP2311825; (2015); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 57054-92-9, 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. 57054-92-9, name is 5-Bromo-2-chloro-4-methoxypyrimidine. A new synthetic method of this compound is introduced below.

Step Y1 : 2-(5-Bromo-4-methoxy-pyrimidin-2-ylamino)-ethanol A mixture of 5-bromo-2-chloro-4-methoxypyrimidine (5 g, 22.4 mmol) and 2-amino ethanol (1.76 mL, 29.1 mmol) in THF (50 mL) was stirred for 18 h at rt. 2-Amino ethanol (2 mL) was added. The reaction mixture was stirred for 18 h at rt and concentrated. The residue was purified by flash chromatography (hexane/EtOAc, 3:2) to afford 4.08 g of the title compound. tR: 0.70 min (LC-MS 2); ESI-MS: 248.2 [M+H]+ (LC-MS 2); Rf: 0.06 (hexane/EtOAc 3:2).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,57054-92-9, 5-Bromo-2-chloro-4-methoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; GUAGNANO, Vito; HOLZER, Philipp; KALLEN, Joerg; LIAO, Lv; MAH, Robert; MAO, Liang; MASUYA, Keiichi; SCHLAPBACH, Achim; STUTZ, Stefan; VAUPEL, Andrea; WO2013/111105; (2013); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 5305-59-9 , The common heterocyclic compound, 5305-59-9, name is 6-Chloropyrimidin-4-amine, molecular formula is C4H4ClN3, 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 solution of 6-chloropyrimidin-4-amine (500 mg) and N,N-dimethylaminopyridine (47.2 mg) in acetonitrile (5.0 mL) was added di-tert-butyl dicarbonate (2.24 mL) at room temperature. The reaction mixture was stirred at room temperature for 3 days, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.13 g). MS (ESI+) : [M+H]+330.2

The synthetic route of 5305-59-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; NAGAMIYA, Hiroyuki; YOSHIDA, Masato; SETO, Masaki; MARUI, Shogo; ODA, Tsuneo; ISHICHI, Yuji; SUZUKI, Hideo; KUSUMOTO, Tomokazu; YOGO, Takatoshi; RHIM, Chul Yun; YOON, Cheolhwan; LEE, Gil Nam; KANG, Hyun Bin; KIM, Kwang Ok; JEON, Hye Sun; EP2818473; (2014); A1;,
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Application of 26032-72-4, Adding some certain compound to certain chemical reactions, such as: 26032-72-4, name is 2,4-Dichloro-6-phenylpyrimidine,molecular formula is C10H6Cl2N2, 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 26032-72-4.

The compound 2,4-dichloro-6-phenylpyrimidine (1.52 g, 6.7 mmol),(+/-)-trans-3-aminobicyclo[2.2.2]octane-2-carboxylic acid methyl ester(1.84 g, 10.0 mmol) was dissolved in N,N-dimethylformamide (10 mL).Potassium carbonate (0.92 g, 6.7 mmol) was then added to the reaction mixture.The resulting mixture was stirred at room temperature overnight. After the reaction is complete,It was diluted with H2O (50 mL), and the mixture was extracted with ethyl acetate (40mL×3).The combined organic phases were washed with saturated brine (50 mL).Dry with anhydrous sodium sulfate, filter, and concentrate the filtrate under reduced pressure.The residue was purified by silica gel column chromatography(n-hexane/ethyl acetate (v/v) = 20/1-10/1)The title compound was obtained as a white solid(1.65g, 66%).

According to the analysis of related databases, 26032-72-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ren Qingyun; Tang Changhua; Yin Junjun; Yi Kai; Lei Yibo; Wang Yejun; Zhang Yingjun; (138 pag.)CN108276401; (2018); A;,
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Pyrimidine – Wikipedia

Reference of 5177-27-5, 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 5177-27-5, name is 5-Amino-2,4-dichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 2,4-dichloropyrimidin-5-amine (0.5 g, 3.04 mmol), sodium methoxide (0.66 g, 12.19 mmol) and methanol (10 ml) was refluxed for 16 hours. The solvent was removed under reduced pressure. Water was added and the aqueous phase was extracted with ethyl acetate. The organic phase was washed with water and brine, dried over sodium sulphate and concentrated under reduced pressure. The yield of 2-chloro-4-methoxypyrimidin-5-amine after flash chromatography (100-200 mesh size silica gel, 20-25% ethyl acetate in hexane) was 0.35 g. N-Bromosuccinimide (67 mg, 0.37 mmol) was added to a solution of 2-chloro-4-methoxypyrimidin-5-amine (50 mg, 0.31 mmol) in chloroform (2 ml) and the resulting mixture was stirred at RT for 3 hours. Water was added and the mixture extracted with chloroform. The organic phase was washed with water and brine, dried over sodium sulphate and concentrated under reduced pressure. The yield of 4-bromo-2-chloro-6-methoxypyrimidin-5-amine was 60 mg.

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 5177-27-5, 5-Amino-2,4-dichloropyrimidine.

Reference:
Patent; MEDEIA THERAPEUTICS LTD; RATILAINEN, Jari; GOLDSTEINS, Gundars; WO2014/191632; (2014); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 13223-25-1, 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.

L-methyl lactate 0.46g (0.005 mol) and 2-Chloro-4,6-dimethoxy-pyrimidine 0.88g (0.005 mol) were dissolved in DMF 20 ml, K2CO3 0.52g (0.75 eq) was added thereto, and sodium methane sulfinate 0.1g was added thereto, followed by stirring at 120C for 5 hours. The reacted solution was cooled to room temperature, and distilled under reduced pressure to obtain residue. The residue was extracted with cold water and ethylacetate (EA) three times, and washed with brine twice, the organic layer was dried with MgSO4, and the solvent was removed under reduced-pressure. Through purification with silica gel column chromatography, a target material 0.66g (54%) was obtained.: 1H NMR (300MHz, CDCl3) delta: 1.63(d, 3H), 3.73(s, 3H), 3.89(s, 6H), 5.22(q, 1H), 5.72(s, 1H).

According to the analysis of related databases, 13223-25-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SNU R&DB Foundation; Korea Research Institute Of Chemical Technology; EP2497768; (2012); A2;,
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Pyrimidine – Wikipedia

Electric Literature of 13162-26-0, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 13162-26-0 as follows.

Cyclopentylamine(5.2ml) and N,N-diisopropylethylamine(13.2ml) were dissolved into 150ml dichloromethane. The mixture was added dropwise to a solution of 2,4-dichloro-5-nitro-6-methylpyrimidine(10.7g) in dichloromethane(30ml) at 0C. After the completion of the dropwise addition, the mixture was kept at the same temperature to react for 1 hour. Purification was conducted by a column chromatography to obtain a bright-yellow solid(11.2g) in a yield of 84.8%. 1H NMR(400 MHz, CDCl3): delta 8.44(s, 2H), 4.41(m, 1H), 2.64(s,3H), 2.01-2.15(m, 2H), 1.61-1.76(m, 4H), 1.45-1.63(m, 2H)ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13162-26-0, its application will become more common.

Reference:
Patent; Si Chuan University; CSPC Zhongqi Pharmaceutical Technology (Shijiazhuang) Co., Ltd.; YANG, Shengyong; WEI, Yuquan; EP2578584; (2013); A1;,
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Application of 60025-09-4, 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 60025-09-4, name is 4-Amino-6-chloropyrimidine-5-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To the solution of 44 (200 mg, 0.664 mmol, 1.1 eq) in t-BuOH(4 mL) were added 6-chloro-9H-purine (93 mg, 0.604 mmol, 1.0 eq)and DIPEA (149 mL, 0.906 mmol, 1.5 eq). The resultant mixture was stirred at 80 C under N2 atmosphere for 8 h and concentrated in vacuo. To the residue was added DCM, and the mixture was washed successively with saturated NaHCO3 solution, dilute hydrochloric acid (0.5 N) and brine. The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. Flash column chromatography utilizing EA/PE (1:1e3:1) and EA/AcOH (80:1) as the eluent afforded a light yellow oil. It was then dissolved in DCM, and the resulting solution was washed successively with saturated NaHCO3 solution, brine, dried over anhydrous Na2SO4, and concentrated in vacuo to afford 3-(1-((9H-purin-6-yl)amino)ethyl)-2-phenyl-2Hbenzo[e][1,2,4]thiadiazine 1,1-dioxide 55 as a light yellow solid.Yield 28%;

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 60025-09-4, 4-Amino-6-chloropyrimidine-5-carbonitrile.

Reference:
Article; Ma, Xiaodong; Wei, Jun; Wang, Chang; Gu, Dongyan; Hu, Yongzhou; Sheng, Rong; European Journal of Medicinal Chemistry; vol. 170; (2019); p. 112 – 125;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 22536-61-4, 2-Chloro-5-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, 22536-61-4, blongs to pyrimidines compound. SDS of cas: 22536-61-4

2-Chloro-5-methyl-pyrimidine (18 mL, 151 mmol), potassium (Z)-but-2-en-2- yltrifluoroborate (commercially available from Sigma Aldrich, 31 g, 191 mmol), tricyclohexylphosphine (8.5 g, 30.2 mmol) and Pd2(dba)3 (13.82 g, 15.09 mmol) were added to a flask, which was then degassed and backfilled with nitrogen. To the flask was added 1,4-dioxane (252 mL) and aqueous potassium phosphate tribasic (37.5 mL, 453 mmol). The resulting reaction was heated at 100 C for 16 h. The reaction was then cooled to RT. The residue was filtered through a plug of silica gel and then loaded onto silica gel (0-20% EtOAc in heptanes) to afford (E)-2-(but-2-en-2-yl)-5-methylpyrimidine 27.01 (19 g, 125 mmol, 83% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22536-61-4, its application will become more common.

Reference:
Patent; AMGEN INC.; CHEN, Yinhong; CHENG, Alan C.; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; HARVEY, James S.; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; LAI, Su-Jen; MA, Zhihua; PATTAROPONG, Vatee; SWAMINATH, Gayathri; KREIMAN, Charles; MOEBIUS, David C.; SHARMA, Ankit; (543 pag.)WO2018/93580; (2018); A1;,
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Pyrimidine – Wikipedia