Tag: M.W:200-300

Related Products of 114040-06-1, 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. 114040-06-1, name is 3-Bromo-5,7-dichloropyrazolo[1,5-a]pyrimidine. A new synthetic method of this compound is introduced below.

To a solution of 3-bromo-5,7-dichloropyrazolo[ l ,5-a]pyrimidine (2.67 g, 10 mmol) in DCM (30 mL) at 0 C was added (tetrahydro-2H-pyran-4- yl)methan-amine ( 1 .27 g, 1 1 mmol), followed by DIPEA (2.1 mL, 12 mmol). The resulting mixture was stirred at rt for l h and purified by flash chromatography (gradient: EtOAc hex 0-90%) to give the title compound as white solid (3.46 g, quantitative yield). NMR (400 MHz, CDCl3) delta ppm 7.96 (s, 1 H), 6.55-6.43 (m, 1 H), 6.00 (s, 1H), 4.08-4.00 (m, 2H), 3.43 (dt, J = 12.0, 1.7 Hz, 2H), 3.32 (t, J = 6.6 Hz, 2H), 2.06-1.94 (m, 1H), 1.78-1.71 (m, 2H), 1.51-1.38 (m, 2H); MS ESI [M + H]+345.1, calcd for [C12H14BrClN40+H]+344.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,114040-06-1, 3-Bromo-5,7-dichloropyrazolo[1,5-a]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; UNIVERSITY HEALTH NETWORK; LIU, Yong; PAULS, Heinz W.; LAUFER, Radoslaw; LI, Sze-Wan; SAMPSON, Peter Brent; FEHER, Miklos; NG, Grace; PATEL, Narendra Kumar B.; LANG, Yunhui; WO2014/75168; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 815610-16-3, 2-Amino-4-iodopyrimidine, 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, 815610-16-3, blongs to pyrimidines compound. Recommanded Product: 815610-16-3

A flask containing a solution of 55-iodide (4.09g, 18.5mmol) in NMP (75ml) was purged with argon for 5min. Zinc cyanide (2.28g, 19.4mmol) and tetrakis(triphenylphosphine)palladium (0) (1.71g, 1.48mmol) were added and the mixture was stirred at 80C for 2h. The mixture was cooled to room temperature, EtOAc (200ml) and 30% aqueous NH4OH (200ml) was added, and stirring was continued for 1h. The layers were separated, the aqueous layer was extracted with EtOAc (4×200ml), and the combined organic layers were concentrated under reduced pressure. Et2O (30ml) was added and the precipitate was collected by filtration and washed with Et2O to deliver 2-aminopyrimidine-4-carbonitrile (1.66g, 13.8mmol, 75% yield) as a white solid. 1H NMR (400MHz, DMSO-d6) delta ppm 8.51 (d, J=4.7Hz, 1H), 7.31 (br. s, 2H), 7.08 (d, J=4.7Hz, 1H). MS (ESI, pos. ion) m/z: 121.1 (M+1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,815610-16-3, its application will become more common.

Reference:
Article; Reichelt, Andreas; Bailis, Julie M.; Bartberger, Michael D.; Yao, Guomin; Shu, Hong; Kaller, Matthew R.; Allen, John G.; Weidner, Margaret F.; Keegan, Kathleen S.; Dao, Jennifer H.; European Journal of Medicinal Chemistry; vol. 80; (2014); p. 364 – 382;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 3974-16-1 , The common heterocyclic compound, 3974-16-1, name is 4,6-Dichloro-5-phenylpyrimidine, molecular formula is C10H6Cl2N2, 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.

C. Preparation of 4-chloro-6-(4-chlorophenyl)-5-phenylpyrimidine To a mixture of 4,6-dichloro-5-phenylpyrimidine (675 mg, 3.0 mmol), 4-chlorophenylboronic acid (704 mg, 4.5 mmol) and tetrakis(triphenylphosphine)palladium (173 mg, 0.15 mmol) in toluene (10 mL) at room temperature under argon was added aqueous Na2CO3 solution (2 M, 3 mL, 6 mmol). The resulting reaction mixture was stirred at 100 C. under argon for 5 h, after which time analysis by HPLC/MS indicated that the the reaction was complete. After cooling the reaction mixture to room temperature, water (15 mL) was added. The resulting mixture was extracted with EtOAc (2*25 mL). The combined organic layers were washed with saturated aqueous NaCl, then dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluted with ethyl acetate-hexanes to obtain 571 mg of the title compound as a white solid. HPLC/MS: retention time=3.85 min, [M+H]30 =301.

The synthetic route of 3974-16-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wu, Gang; Mikkilineni, Amarendra B.; Sher, Philip M.; Murugesan, Natesan; Gu, Zhengxiang; US2006/287341; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 886365-79-3 , The common heterocyclic compound, 886365-79-3, name is 5-Bromo-2-(2-methoxyethylamino)pyrimidine, molecular formula is C7H10BrN3O, 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.

Synthesis of 4-(4-{2-[(2-methoxyethyl)amino]pyrimidin-5-yl}phenyl)-N- [5-(2-methyl-l,3-thiazol-4-yl)pyridin-2-yl]tetrahydro-2H-pyran-4-carboxamide (example 207)To a solution of 1-105 (75 mg, 0.16 mmol), KOAc (157 mg, 1.6 mmol),PdCi2(dppf).CH2Ci2 (33 mg, 0.04 mmol) in dioxane (2.0 mL) at room temperature is added R-8 (115 mg, 0.46 mmol). The reaction mixture is heated at 100 C in a sealed tube for 16 hours. The reaction mixture is allowed to cool to room temperature, followed by the addition R-31 (88 mg, 0.38 mmol) in THF (2.0 mL), 20% Na2C03 solution (2.0 mL), and Pd(PPh3)4 (23 mg, 0.20 mmol). The reaction mixture is heated in the microwave at 120 C for 60 minutes, allowed to cool to room temperature, and partitioned between EtOAc and H20. The combined organics are washed with H20, dried with Na2S04, filtered, and concentrated in vacuo. The residue is purified by flash chromatography (Si02, 0-10% MeOH in EtOAc) to give the title compound 207 (36 mg).

The synthetic route of 886365-79-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BERRY, Angela; CHEN, Zhidong; DE LOMBAERT, Stephane; EMMANUEL, Michel Jose; LOKE, Pui Leng; MAN, Chuk Chui; MORWICK, Tina Marie; TAKAHASHI, Hidenori; WO2012/82817; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1189973-29-2, 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 1189973-29-2, name is (1-(5-Bromopyrimidin-2-yl)piperidin-3-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

Step 2: Synthesis of {l-[5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyrimidin-2- yl]piperidin-3-yl}methanol :; To a solution of [l-(5-bromopyrimidin-2-yl)piperidin-3-yl]methanol (0.5 g, 1.83 mmol) in 1,4 dioxane (25 mL) were added bispinacolatodiborane (0.46 g, 3.3 mmol), potassium acetate ( 0.53 g, 5.4 mmol) and Pd (dppf)Cl2 (0.14 g, 0.18 mmol) under argon at room temperature (~25 0C). The mixture was heated at 80-90 0C for about 6 hours. It was cooled to room temperature (-25 0C), concentrated under reduced pressure and then purified through filtering column using sintered funnel full of 230-400 mesh size silica gel. It was eluted with 50% ethyl acetate in hexane and concentrated to afford title compound (0.4 g). MS m/e 289.93 (MH+).

According to the analysis of related databases, 1189973-29-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; WO2009/156966; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.1211522-68-7, name is 4,6-Dichloro-3-methyl-1H-pyrazolo[3,4-d]pyrimidine, molecular formula is C6H4Cl2N4, molecular weight is 203.0288, as common compound, the synthetic route is as follows.Quality Control of 4,6-Dichloro-3-methyl-1H-pyrazolo[3,4-d]pyrimidine

To a solution of 2,4-dichloropyrrolo[1,2-f][1,2,4]triazine (4a) (0.5 g, 2.7 mmol) in 2-Propanol (6 mL) was added (S)-pyrrolidin-2-ylmethanol (0.39 mL, 4.0 mmol), DIPEA (1.39 mL, 8.0 mmol) and heated at 90 C for 1 hr. The reaction was cooled to room temperature and solid obtained was collected by filtration to afford (S)-(l-(2-chloropyrrolo[2,l-f][l,2,4]triazin-4- yl)pyrrolidin-2-yl)methanol (96a) (0.49 g, 73 % yield) as a white solid; NMR (300 MHz, DMSO-i/e): delta 7.70 (dd, J= 2.6, 1.4 Hz, 1H), 6.97 (dd, J= 4.7, 1.6 Hz, 1H), 6.80 – 6.57 (m, 1H), 5.15 (t, J = 5.7 Hz, 1H, D2O exchangeable), 4.87 (t, J= 5.7 Hz, 1H), 4.44 (d, J= 17.8 Hz, 1H), 4.05 – 3.82 (m, 1H), 3.72 – 3.39 (m, 2H), 2.22 – 1.84 (m, 4H). MS (ES+): 253.3, 255.3 (M+2); MS (ES-): 287.2, 289.2 (M+Cl).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1211522-68-7, 4,6-Dichloro-3-methyl-1H-pyrazolo[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.313339-35-4, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid, molecular formula is C6H4Cl2N2O2S, molecular weight is 239.08, as common compound, the synthetic route is as follows.name: 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid

Thionyl chloride (1.6 mL, 22.1 mmol) and DMF (0.025 mL) were added to 4,6-dichloro-2-(methylthio)-pyrimidine-5-carboxylic acid (528 mg, 2.21 mmol) obtained in Reference Example 4, and the mixture was stirred at 90C for 4 hours. The mixture was concentrated under reduced pressure, and the residue was dried for 12 hours under reduced pressure. The resulting residue was dissolved in dichloromethane (11 mL), and the mixture was stirred at -78C for 30 minutes after triethylamine (0.25 mL, 1.76 mmol), and a dichloromethane (11 mL) solution of the (S)-2-(aminomethyl)pyrrolidine-1-carboxylic acid tert-butyl ester (295 mg, 1.47 mmol) obtained in Reference Example 6 were added at -78C. Thereafter, a saturated aqueous ammonium chloride solution and ethyl acetate were added to separate the organic layer. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give (S)-N-[(1-tert-butoxycarbonylpyrrolidin-2-yl)methyl]-4,6-dichloro-2-methylthiopyrimidine-5-carboxylic acid amide (538 mg, 87%). ESI-MS: m/z 421 [M + H]+. 1H-NMR (CDCl3) delta(ppm): 1.43 (s, 9H), 1.70-2.00 (m, 3H), 2.08 (m, 1H), 2.58 (s, 3H), 3.32-3.46 (m, 3H), 3.60 (m, 1H), 4.10 (m, 1H), 8.24 (brs, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,313339-35-4, 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2163554; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia