Category: pyrimidines

Application of 17326-27-1 , The common heterocyclic compound, 17326-27-1, name is 2-Chloro-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde, molecular formula is C10H7ClN2O2, 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.

222.6mg (1mmol) 2- chloro-3-aldehyde-4-carbonyl methylpyridine -4H-9- [1,2-alpha] pyrimidine 5mL of absolute ethanol was added a solution of 484.7mg (4mmol ) phenethylamine, rt 12h, after the reaction was filtered, the solid washed thoroughly with ethanol to give a pale yellow solid 320.2mg, 78% yield.

The synthetic route of 17326-27-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Chinese Academy Of Sciences Beijing Genome Institute; Yang Caiguang; Liu Jiang; Luo Cheng; Guo Zhongqiang; Gong Shouzhe; Li Jiafei; Zheng Tong; Jiang Hualiang; (46 pag.)CN107141287; (2017); A;,
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Application of 29939-37-5, 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 29939-37-5 as follows.

A mixture comprising 5.0 g (39.6 mmol) 6-hydrazinopyrimidin-4-ol/6-hydrazinopyrimidin- 4(1 H)-one (CAS-No: 29939-37-5), 5.12 g pentan-3-one and 80.8 mL ethanol was heated under reflux for 2 hours. After cooling to 3C, the precipitated solid was filtered off and washed with diethyl ether to give 5.82 g (72%) of the title compound

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,29939-37-5, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KLAR, Ulrich; WORTMANN, Lars; KETTSCHAU, Georg; GRAHAM, Keith; RICHTER, Anja; LIENAU, Philip; PUEHLER, Florian; PETERSEN, Kirstin; SIEGEL, Franziska; SUeLZLE, Detlev; WO2015/4024; (2015); A1;,
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Electric Literature of 60025-06-1, Adding some certain compound to certain chemical reactions, such as: 60025-06-1, name is 1-(4,6-Dichloropyrimidin-5-yl)ethanone,molecular formula is C6H4Cl2N2O, 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 60025-06-1.

3.82 g (20.0 mmol) of 1-(4,6-dichloropyrimidine-5-yl)ethane-1-one was dissolved in 30 mL of dichloromethane, which was cooled down to 0 C., to which 3.88 g (30.0 mmol) of diisopropylethylamine and 3.29 g (24.0 mmol) of p-methoxybenzylamine (PMBNH2) were added stepwise. 1 hour later, the reaction mixture was heated to room temperature, followed by stirring at room temperature for 6 hours. Water and ethylacetate were added to the reaction mixture, followed by extraction. The extracted organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was separated by column chromatography (SiO2, eluent: hexane/ethylacetate, 3/1) to give 5.54 g of the target compound 1-(4-chloro-6-((4-methoxybenzyl)amino)pyrimidine-5-yl)ethane-1-one as a white solid (19.0 mmol, yield: 95%). 1H NMR(300 MHz, CDCl3) delta 9.07 (br s, 1H, NH), 8.38 (s, 1H), 7.25 (d, J=8.1 Hz, 2H), 6.88 (d, J=8.1 Hz, 2H) , 4.67 (d, J=4.8 Hz, 2H) , 3.81 (s, 3H) , 2.74 (s, 3H).

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. 60025-06-1, 1-(4,6-Dichloropyrimidin-5-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; Lee, Ge Hyeong; Lim, Hee-Jong; Cho, Heeyeong; Park, Woo Kyu; Kim, Seong Hwan; Choi, Jung Hwan; (148 pag.)US2018/105527; (2018); A1;,
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Electric Literature of 1245506-61-9, 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 1245506-61-9, name is 2-Chloro-5-methoxy-4-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To a -78 C solution of Intermediate 3B (1.60 g, 10.09 mmol) in DCM (20 mL) was added BBr3 (3.82 mL, 40.4 mmol) dropwise. The reaction mixture was allowed to slowly warm to RT and stirred for 16 h at RT, then was cautiously quenched with satd aq. NaHC03 (pH adjusted to ~4) and partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc (2x), and the combined organic layers were dried (MgS04) and concentrated in vacuo. The crude product was chromatographed (40 g S1O2; continuous gradient from 0-100% EtOAc in Hexane over 15 min) to afford the title compound (1.33 g, 9.20 mmol, 91 % yield) as a white solid. NMR (400 MHz, DMSO- d6) d 10.63 (s, 1H), 8.11 (s, 1H), 2.34 (s, 3H).

According to the analysis of related databases, 1245506-61-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SHI, Yan; CHENG, Peter Tai Wah; ZHANG, Hao; LI, Jun; FANG, Tianan; CORTE, James R.; (135 pag.)WO2019/126103; (2019); 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.93587-23-6, name is 7-Bromo-1H-pyrrolo[3,2-d]pyrimidin-4(5H)-one, molecular formula is C6H4BrN3O, molecular weight is 214.02, as common compound, the synthetic route is as follows.COA of Formula: C6H4BrN3O

Under argon atmosphere, a solution of 7-Bromo-3,5-dihydro-pyrrolo[3,2-d]pyrimidin-4-one (500 mg, 2.33 mmol) in phosphorus(V) oxychoride (6 rriL) was refluxed for 2 hours. The reaction mixture was then cooled to room temperature, concentrated and the residue was diluted with ethyl acetate. The organic layer was washed with a solution of sodium bicarbonate, brine, dried over sodium sulfate, filtered and evaporated under reduced pressure to afford compound (66a) as a pale solid (490 mg, 2.10 mmol, 90%) without further purification. lH NMR (400 MHz, DMSO-i delta 8.24 (d, J = 3.0 Hz, 1H), 8.72 (s, 1H), 12.95 (bs, 1H). MS m/z ([M+H]+) 232/234

At the same time, in my other blogs, there are other synthetic methods of this type of compound,93587-23-6, 7-Bromo-1H-pyrrolo[3,2-d]pyrimidin-4(5H)-one, and friends who are interested can also refer to it.

Reference:
Patent; LABORATOIRE BIODIM; ATAMANYUK, Dmytro; CHEVREUIL, Francis; FAIVRE, Fabien; GERUSZ, Vincent; GOLD, Johan; MOREAU, Francois; SIMON, Christophe; WO2015/128334; (2015); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 98138-75-1, name is 6-Chloro-4-methoxy-1H-pyrazolo[3,4-d]pyrimidine, the common compound, a new synthetic route is introduced below. HPLC of Formula: C6H5ClN4O

Step 2: To a solution of 6-chl oro-4-m ethoxy- li7-pyrazolo[3,4- (1227) 1.7 g, 9.2 mmol) in DMF (20 mL) was added NaH (552.6 mg, 13.8 mmol, 60% in mineral oil). After 10 min, SEM-C1 (2.3 g, 13.8 mmol, 2.5 mL) was added. The reaction mixture was stirred at 25 C for 1 hour under an atmosphere of nitrogen. The reaction mixture was concentrated under reduced pressure. The residue was diluted with water (30 mL) and extracted with EtOAc (2 x 30 mL). The combined organic layers were washed with water (2 x 30 mL), dried over anhydrous Na2S04, filtered, and concentrated under reduced pressure to give a residue, which was purified by column chromatography (5-20% EtO Ac/petroleum ether). The desired 6-chl oro-4-methoxy-l -((2-(tri methyl si lyl)ethoxy)methyl)- l H- pyrazolo[3,4-i/]pyrimidine (1.3 g, 45.0% yield) was obtained as a light pink solid along with major impurity 6-chl oro-4-methoxy-2-((2-(tri methyl si lyl)ethoxy)methyl)-2//-pyrazolo[3, 4- i/]pyrimidine (520.0 mg, 17.9% yield), which was obtained as a light yellow solid.

The synthetic route of 98138-75-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; WALTERS, W., Patrick; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; TAYLOR, Alexander, M.; PIERCE, Levi Charles, Thomas; MURCKO, Mark, Andrew; GIORDANETTO, Fabrizio; GREISMAN, Jack, Benjamin; MARAGAKIS, Paul; BHAT, Sathesh; KONZE, Kyle; DAHLGREN, Markus, Kristofer; THERRIEN, Eric; (0 pag.)WO2019/165073; (2019); 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 122567-97-9, name is ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate

5-methyl thymine 20-2 as a raw material, the reaction steps are as follows:(3) Synthesis of compound 21-3 (d4T):Compound 21-2 (0.288 g, 0.88 mmol) was added to the reactor,Saturated methanolic methanol solution 30mL, stirring at room temperature reaction,TLC tracks the reaction to the end. The solvent was removed by concentration,Column chromatography (MeOH: CHCl3 = 5: 100)To give the target product 21-3 (yield 75%).

With the rapid development of chemical substances, we look forward to future research findings about 122567-97-9.

Reference:
Patent; Soochow University (Suzhou); Zou Jianping; Zhang Peizhi; Li Jianan; (13 pag.)CN106496130; (2017); A;,
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Synthetic Route of 216309-28-3 ,Some common heterocyclic compound, 216309-28-3, molecular formula is C9H12N2Si, 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.

b) 5-Ethynyl-pyrimidine; Potassium carbonate (7.38 g, 53.4 mmol) was added in one portion to a stirred solution of 5-trimethylsilanylethynyl-pyrimidine (4.71 g, 26.7 mmol) in methanol (10 ml). The reaction mixture was stirred for 2 hours at room temperature then concentrated in vacuo. The residue was suspended in dichloromethane and the inorganic solids were removed by filtration. The filtrate was concentrated in vacuo to remove ca. 95% of the solvent to afford 5-ethynyl-pyrimidine as a brown oil in crude form. This material was used in the subsequent Sonogashira reaction without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,216309-28-3, its application will become more common.

Reference:
Patent; Hebeisen, Paul; Roever, Stephan; US2008/70931; (2008); A1;,
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Electric Literature of 19808-30-1, 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.19808-30-1, name is 5-Bromopyrimidin-4(3H)-one, molecular formula is C4H3BrN2O, molecular weight is 174.9834, as common compound, the synthetic route is as follows.

Reference Example 3 5-Bromopyrimidin-4(3H)-one (578 mg) was dissolved in N,N-dimethylformamide (15 mL), and potassium carbonate (685 mg) and methyl iodide (247 muL) were added, followed by stirring at room temperature for 24 hours. Water was added to the reaction mixture, followed by extraction with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 1:1) to obtain 5-bromo-3-methylpyrimidin-4(3H)-one (337 mg) as a white solid.

The chemical industry reduces the impact on the environment during synthesis 19808-30-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Astellas Pharma Inc.; EP1947086; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 313339-35-4, 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. 313339-35-4, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid, molecular formula is C6H4Cl2N2O2S, 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.

Method same In Example 1, 0.49 g (2.03 mmol) of 4,6-dichloro-2-(methylsulfanyl)pyrimidine-5-carboxylic acid was dissolved in 20 mL of methylene chloride solvent, 0.52 g (4.06 mmol) of oxalyl chloride was added, DMF, stirred for 5 h at room temperature and the solvent and excess oxalyl chloride removed in vacuo to give a yellow solid; this was dissolved in 20 mL of dichloromethane and then 0.37 g (2.03 mmol) of 5-[(methylamino)methyl]-1H-imidazole-4-ethylformate,0.35g (3.45mmol) of triethylamine, stirred at room temperature After the reaction was completed, it was poured into 30mL of saturated sodium bicarbonate solution, extracted with dichloromethane (20mLX2), combined organic phase, dried over anhydrous sodium sulfate, filtered After the solvent was distilled off under reduced pressure, 5-((4,6-dichloro-N-methyl-2-(methylsulfanyl)pyrimidine-5-carboxamido)methyl)-1H-imidazole-4-ethylformate was obtained, used directly in the next reaction.5-((4,6-dichloro-N-methyl-2-(methylsulfanyl)pyrimidine-5-carboxamido)methyl)-1H-imidazole-4-ethylformate was dissolved in 20 mL of acetonitrile , 0.98g (7. 10mmol) of anhydrous potassium carbonate was added and the mixture was stirred at room temperature until the reaction was completed. The solvent was distilled off under reduced pressure.This was dissolved in 20 mL of methylene chloride, washed with 30 mL of saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure and the residue was purified by column chromatography (CH2C12: CH3COCH3 = 60: 1) to give a white solid The yield is 27%.0.35g (1.71mmol) of 4-chloro-2-(methylsulfanyl)pyrimidine-5-carboxylic acid was dissolved in 20mL dichloromethane solvent, 0.37g (2.94mm0l) oxalyl chloride was added, 1 drop DMF, stirred at room temperature for 6h and then under reduced pressure Evaporation of solvent and excess oxalyl chloride gave a yellow solid;This was dissolved in 20 mL of dichloromethane and then 0.22 g (1.21 mmol) of 5-[(methylamino)methyl]-1H-imidazole-4-ethylformate and 0.21 g (2.05 mmol) of triethylamine were added and stirred at room temperature After the reaction, it was poured into 30 mL of saturated sodium bicarbonate solution and extracted with dichloromethane (20 mL × 2). The combined organic phase was dried over anhydrous sodium sulfate and filtered. The solvent was evaporated under reduced pressure to give 5-((4-chloro-N-methyl-2-(methylsulfanyl)pyrimidine-5-carboxamido)methyl)-1H-imidazole-4-ethylformate was used directly in the next reaction.A solution of ethyl 5-((4-chloro-N-methyl-2-(methylsulfanyl)pyrimidine-5-carboxamido)methyl)-1H-imidazole-4-ethylformate in 20 mL of acetonitrile was added 0.58 g 4.22 mmol) anhydrous potassium carbonate and stirred at room temperature until the reaction was completed. The solvent was distilled off under reduced pressure.The residue was dissolved in 20 mL of methylene chloride, washed with 30 mL of saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure and the residue was purified by column chromatography (CH2C12: CH3COCH3 = 10: 1) to give a white solid The yield is 60%.

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 313339-35-4, 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid.

Reference:
Patent; Beijing Normal University; The Chinese People’s Liberation Army Military Academy Of Medical Sciences Poison Pharmaceutical Institute; Zhang Zhanbin; Yu Gang; Li Yi; Xiao Guiying; Cao Yanqing; Su Ruibin; Zheng Zhibing; Zhou Xinbo; (12 pag.)CN107312012; (2017); A;,
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