Category: pyrimidines

Reference of 1224944-77-7 ,Some common heterocyclic compound, 1224944-77-7, molecular formula is C9H8ClN3O2, 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.

ompound 4 (2 g, 10.5 mmol) and Compound 7 (2.4 g, 10.5 mmol)Add to n-butanol (50 mL) in turn, then add diisopropylethylamine (10.8 g, 84 mmol).The temperature was raised to 120 C and stirred overnight, and TLC showed that the starting material disappeared.N-butanol is removed under reduced pressure,Water (50 mL) was added to the residue.Extracted with ethyl acetate (50 mL*3).The organic phases were combined and dried over anhydrous magnesium sulfate.Filtration, concentration, silica gel column chromatography (PE: EA = 1:1)Obtained a white solid 8 (3.1 g),The generation rate is 97%.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 1224944-77-7, Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhengzhou Taijihongnuo Pharmaceutical Co., Ltd.; Wu Yusheng; Zhi Wubin; Li Jingya; Wang Xin; Wu Shiyong; Liang Apeng; Guo Ruiyun; (31 pag.)CN109516999; (2019); A;,
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. 7752-72-9, name is 5-Chloro-6-methylpyrimidin-4(3H)-one. This compound has unique chemical properties. The synthetic route is as follows. name: 5-Chloro-6-methylpyrimidin-4(3H)-one

14.5g (0.1mol) 4- hydroxy-5-chloro-6-methylpyrimidine dissolved in 50ml of toluene, was added dropwise with stirring to the reaction flask 50ml phosphorus oxychloride, after dropwise addition the reaction heated at reflux for 5-7 hours, TLC monitored after completion of the reaction. Toluene was evaporated under reduced pressure and excess phosphorus oxychloride, with stirring the reaction was poured into ice water, the aqueous phase was extracted with ethyl acetate (3 × 50ml), the combined organic phase was dried over anhydrous magnesium sulfate, filtered, and dissolved. The residue was purified by column chromatography (eluent, ethyl acetate and petroleum ether (boiling range 60-90 deg. C), the volume ratio of 1: 4) was isolated as a yellow liquid 14.43g, yield 88.5%.

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, 7752-72-9, 5-Chloro-6-methylpyrimidin-4(3H)-one.

Reference:
Patent; Sinochem Agrochemicals R & D Co., Ltd.; Guan, Aiying; Yang, Fan; Wang, Junfeng; Chen, Wei; Fan, Xiaoxi; Wang, Xiuli; Chen, Xuanming; Li, Keke; Li, Zhinian; Liu, Zhangling; (73 pag.)CN105732585; (2016); A;,
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Electric Literature of 1780-26-3, 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.1780-26-3, name is 2-Methyl-4,6-dichloropyrimidine, molecular formula is C5H4Cl2N2, molecular weight is 163.0047, as common compound, the synthetic route is as follows.

To 12 ml of 1,4-dioxane, 0.75 g of phenylboronic acid, 1.67 g of potassium carbonate, 0.13 g of dichlorobis (triphenylphosphine) palladium and 1 g of 4,6- dichloro-2-methylpyrimidine were added. This mixture was stirred at 60C for 3 hours and then stirred at 800C for 6 hours. The reaction mixture was left standing to cool to room temperature, poured into an aqueous saturated ammonium chloride solution and then extracted three times with tert- butyl methyl ether. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography to obtain 0.64 g of 4-chloro-2-methyl- 6-phenylpyrimidine.4-chloro-2-methyl-6-rhohenylpyrimidine 1 H-NMR : 2 . 78 ( s , 3H ) , 7 . 49-7 . 56 (m, 4H ) , 8 . 04 -8 . 07 (m, 2H )

Statistics shows that 1780-26-3 is playing an increasingly important role. we look forward to future research findings about 2-Methyl-4,6-dichloropyrimidine.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; MIZUNO, Hajime; WO2010/134478; (2010); A1;,
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Application of 3932-97-6, 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 3932-97-6 as follows.

Step 1: To a solution of 60_1 (2.00 g, 9.22 mmol, 1.00 eq) in THF (40 mL) was added ZnCi2-Et20 (1 M, 11.06 mL, 1.20 eq) at 0C under nitrogen protection. The mixture was stirred for 2 hours at 0C. Methylsulfanylsodium (646.23 mg, 9.22 mmol, 02429524H5-01 – TO SS?.48 muL·, 1.00 eq) was added. The resulting mixture was stirred at 20C for 16 hours. TLC (pure PE) showed reactant 1 (Rf=0.5) consumed and product (Rf=0.3) formed. The mixture was quenched with 1M HC1 (20 mL) and concentrated. The aqueous layer was extracted with DCM (20 mL*3). The combined organic layer was concentrated and purified by silica gel column (PE: EA=1 :0~50: 1) to give 60_2 (1.00 g, 1.97 mmol, 21.4% yield, 45.1% purity) as colorless oil. LCMS: RT = 0.794 min, mlz 228.9 [M+H]+ NMR (CDC13, 400 MHz) delta 8.67 (s, 1H), 2.62 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3932-97-6, its application will become more common.

Reference:
Patent; YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM LTD; BEN NERIAH, Yinon; BRACHYA, Guy; BURSTAIN, Ido; MINZEL, Waleed; SNIR-ALKALAY, Irit; VACCA, Joseph; LI, Dansu; (129 pag.)WO2017/21969; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 125401-75-4, 2,6-Bis((4,6-dimethoxypyrimidin-2-yl)oxy)benzoic acid, 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 2,6-Bis((4,6-dimethoxypyrimidin-2-yl)oxy)benzoic acid, blongs to pyrimidines compound. Quality Control of 2,6-Bis((4,6-dimethoxypyrimidin-2-yl)oxy)benzoic acid

EXAMPLE 8 Ammonium 2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate (Compound No. 22) 2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoic acid (5.1 g) and 28% aqueous ammonia (1.7 g) were mixed with a solvent mixture of THF/ethanol. Precipitated crystals were washed with acetone to obtain the above identified compound as white crystals (3.7 g). (Melting point: 135-140 C.

The synthetic route of 125401-75-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kumiai Chemical Industry Co., Ltd.; Ihara Chemical Industry Co., Ltd.; US4906285; (1990); A;,
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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. 54535-00-1, name is (5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanol. A new synthetic method of this compound is introduced below., Recommanded Product: (5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanol

Under ice bath, intermediate b3 (2.0 g, 11.0mmol) was solubilized in dichloromethane (10 mL). a solution ofthionyl chloride (12.0 mmol) in dichloromethane (10 mL) wasadded drop-wise. The mixture was stirred at rt for 3 h. After that,the solvent was removed under reduced pressure and ethyl acetatewas added, then the mixture was washed by saturated sodiumbicarbonate solution followed by brine, and dried with Na2SO4, filteredand evaporated in vacuo to get yellow solid (1.9 g, 89%). MS[M+H]+ m/z: 197.

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, 54535-00-1, (5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanol.

Reference:
Article; Liu, Moyi; Xu, Qiaoling; Guo, Su; Zuo, Ruixi; Hong, Yue; Luo, Yong; Li, Yingxiu; Gong, Ping; Liu, Yajing; Bioorganic and Medicinal Chemistry; vol. 26; 9; (2018); p. 2621 – 2631;,
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Application of 1197953-49-3, 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 1197953-49-3, name is (2-((2,5-Dichloropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide. This compound has unique chemical properties. The synthetic route is as follows.

171 mg of compound c25-12 and 165 mg of compound b3-1 were dissolved in 13 mL of ethylene glycol monomethyl ether and 0.43 mL of ethanol, and 0.26 mL of a hydrogen chloride solution (5.6 M) was added thereto, and the mixture was reacted at 120 C for 18 hours.The solvent was removed under reduced pressure, water was added to PH 9 with potassium carbonate, extracted with dichloromethane, dried, concentrated, obtained by column chromatography 24mg compound c-25;

According to the analysis of related databases, 1197953-49-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhejiang Tongyuankang Pharmaceutical Co., Ltd.; Wu Yusheng; Zhi Wubin; Wang Xin; Wu Shiyong; Li Jingya; Guo Ruiyun; Zheng Maolin; Liang Apeng; Wang Guohui; Chen Mingtao; Ma Jie; Niu Chengshan; (65 pag.)CN108689994; (2018); A;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 153435-63-3, 2-(Tributylstannyl)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 2-(Tributylstannyl)pyrimidine, blongs to pyrimidines compound. Safety of 2-(Tributylstannyl)pyrimidine

EXAMPLE 889-Amino-2-cyclobutyl-5-pyrimidin-2-yl-2,3-dihydropyrrolo[3,4-b]quinolin-1-one9-amino-5-bromo-2-cyclobutyl-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-one (306 mg, 0.92 mmol), CombiPhos-Pd6 (46.1 mg, 0.09 mmol), 2-(tributylstannyl)-pyrimidine (680 mg, 1.84 mmol) and N,N-dicyclohexylmethylamine (252 mg, 1.29 mmol) in DMF (5 mL) were heated at 100 C. for 48 hours. Then, the reaction mixture was cooled to room temperature, diluted with methylene chloride (100 ml), washed with water, dried through magnesium sulfate and evaporated to dry. The crude product was purified by column chromatography three times eluted with 20-100% ethyl acetate in hexane, 0-100% CAN in chloroform and 0-5% methanol in methylene chloride to afford the title compound as a yellow solid (26 mg, 8.5%). 1H NMR (500 MHz, CHLOROFORM-d) delta ppm 8.93 (d, J=4.9 Hz, 2 H) 7.96 (t, J=7.2 Hz, 2 H) 7.56 (dd, J=8.2, 7.3 Hz, 1 H) 7.33 (t, J=5.0 Hz, 1 H) 6.41 (br. s., 2 H) 4.90 (quintet, J=8.7 Hz, 1 H) 4.46 (s, 2 H) 2.19-2.30 (m, 4 H) 1.71-1.83 (m, 2 H). MS APCI, m/z=332.3 (M+H). HPLC 1.63 min.

The synthetic route of 153435-63-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; US2008/318943; (2008); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 6693-08-9, 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. 6693-08-9, name is 2,4,6-Trichloro-5-fluoropyrimidine. A new synthetic method of this compound is introduced below.

2,4,6-trichloro-5-fluoropyrimidine (1.54 g, 7.65 mmol),(2S,3S)-3-Aminobicyclo[2.2.2]octane-2-carboxylic acid ethyl ester hydrochloride (1.79 g, 7.65 mmol)And K2CO3 (2.64 g, 19.12 mmol) was suspended in DMF (15 mL).The resulting mixture was stirred at room temperature overnight.The reaction solution was quenched by adding H 2 O (50 mL).Extract with ethyl acetate (50 mL × 3),The combined organic phases were washed with saturated brine (100 mL×3).Dry over anhydrous sodium sulfate, filter, and concentrate the filtrate.The residue was purified by silica gel column chromatography (EtOAc /EtOAcThe title compound was obtained as a pale yellow solid(0.69g, 25%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6693-08-9, 2,4,6-Trichloro-5-fluoropyrimidine, and friends who are interested can also refer to it.

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 5424-21-5, 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.5424-21-5, name is 2,4-Dichloro-6-methylpyrimidine, molecular formula is C5H4Cl2N2, molecular weight is 163.0047, as common compound, the synthetic route is as follows.

A mixture of 2,4-dichloro-6-methyl-pyrimidine (40 g, 245 mmol) in NH3.H2O (500 mL) was stirred at 25 C for 44 h. The crude product was filtered and the resulting solution was concentrated under reduced pressure. The remaining residue was purified by silica gel chromatography to afford 2-chloro-6-methyl-pyrimidin-4-amine (10.4 g, 72.4 mmol, 30% yield) as a white solid. LCMS (ESI): m/z: [M +H] calculated for C5H7QN3 : 144.0; found 144.3.

The chemical industry reduces the impact on the environment during synthesis 5424-21-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; REVOLUTION MEDICINES, INC.; KOLTUN, Elena S.; AAY, Naing N.; BUCKL, Andreas; MELLEM, Kevin T.; BLANK, Brian R.; PITZEN, Jennifer; WANG, Gang; JOGALEKAR, Ashutosh S.; WON, Walter S.; TZITZILONIS, Christos; LI, Jie Jack; GILL, Adrian Liam; CREGG, James Joseph; (207 pag.)WO2019/118909; (2019); A1;,
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Pyrimidine – Wikipedia