Day: December 24, 2020

Related Products of 862730-04-9, 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.862730-04-9, name is 3-Iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine, molecular formula is C8H10IN5, molecular weight is 303.1, as common compound, the synthetic route is as follows.

Synthesis of 3-(3-bromo-5-methoxyphenyl)-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (BA85); A solution of 2-(3-bromo-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (137 mg, 0.43 mmol) in EtOH (3.3 ml) was added to a solution of 3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (65 mg, 0.216 mmol) in DME (12 ml). Pd(PPh3)4 (30 mg, 0.03 mmol) and saturated Na2CO3 (1.9 ml) were added and the reaction was heated to 80 C. under an argon atmosphere overnight. After cooling, the reaction was extracted with saturated NaCl and CH2Cl2. Organic phases were combined, concentrated in vacuo and purified by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA85 (28 mg, 36% yield). ESI-MS (M+H)+ m/z calcd 362.1, found 362.0.

Statistics shows that 862730-04-9 is playing an increasingly important role. we look forward to future research findings about 3-Iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine.

Reference:
Patent; Regents of the University of California; US2007/293516; (2007); 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. 7752-82-1, name is 5-Bromopyrimidin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C4H4BrN3

General procedure: A mixture of bromo compound (1 .0 eq.) and bis(pinacolato)diboron (1 .1 eq.) and potassium acetate (2.0 eq.) dissolved in 1 ,4-dioxane (10 vol) was degassed with argon gas for 15 mm. Subsequently, PdCI2(dppf)CH2C12 (0.05 eq.) was added and the reaction mixture was stirred at 85-100 CC for 16 h. The reaction mixture (generally black color) was filtered and concentrated under reduced pressure. The resulting black mixture was used further without any purification. Intermediate 1-40 was prepared according to the general boronic ester synthesis procedure A by utilizing 5-bromopyrimidin-2-amine (reaction time: 5 h, temperature: 100C). 1H NMR (400 MHz, DMSO) 68.59(s, 2H), 5.43 (brs, 2H), 1.32 (5, 12H);

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, 7752-82-1, 5-Bromopyrimidin-2-amine.

Reference:
Patent; IRM LLC; NOVARTIS AG; CHATTERJEE, Arnab Kumar; NAGLE, Advait Suresh; PARASELLI, Prasuna; KONDREDDI, Ravinder Reddy; LEONG, Seh Yong; MISHRA, Pranab Kumar; MOREAU, Robert Joseph; ROLAND, Jason Thomas; SIM, Wei Lin Sandra; SIMON, Oliver; TAN, Liying Jocelyn; YEUNG, Bryan KS; ZOU, Bin; BOLLU, Venkatataiah; WO2014/78802; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 58347-49-2, 7-Chloropyrazolo[1,5-a]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, 58347-49-2, blongs to pyrimidines compound. Formula: C6H4ClN3

A solution of 7-chloropyrazolo[1,5-ajpyrimidine (0.05 g, 0.326 mmol), (8)-tert-butyl (1 -(2-chloro-4-(4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)phenoxy)-2,4-dimethylpentan-2-yl)carbamate (prepared as described in Example 260, Part A and B) (0.152 g, 0.326 mmol), C52CO3 (0.212 g, 0.65 1 mmol), and KBr (0.039 g, 0.326 mmol) in 1,4-dioxane (10 mL) and water (1 mL) was purged with nitrogen gas for 30 mi PdC12 (dppf)-CH2C12 adduct (0.027 g, 0.033 mmol) was added to the reactionmixture and the solution was purged with nitrogen gas again for 10 mm. The reaction mixture was heated at 80 C for 12 h. The reaction mixture was concentrated and the residue obtained was dissolved in ethyl acetate (30 mL) and water (30 mL). The biphasic mixture was filtered through diatomaceous earth. The diatomaceous earth was washed with ethyl acetate (50 mL). The organic layer wasseparated, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford cmde product as a brown solid which was purified by silica-gel column chromatography (pet ether/ethyl acetate) to afford (5)-tert-butyl (1 -(2-chloro-4- (pyrazolo [1,5 -aj pyrimidin-7-yl)phenoxy)-2,4-dimethylpentan-2-yl)carbamate (0.08 g, 0.174 mmol, 54% yield) as an off-white solid. LCMS (ESI) m/e 459.2 [(M+H) ,calcd for C24H32C1N403 459.21; LC/MS retention time (Method Al): tR = 3.28 mm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58347-49-2, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BRONSON, Joanne J.; CHEN, Ling; DITTA, Jonathan L.; DZIERBA, Carolyn Diane; JALAGAM, Prasada Rao; LUO, Guanglin; MACOR, John E.; MAISHAL, Tarun Kumar; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; SISTLA, Ramesh Kumar; THANGAVEL, Soodamani; (318 pag.)WO2017/59080; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1193-21-1, 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. 1193-21-1, name is 4,6-Dichloropyrimidine, molecular formula is C4H2Cl2N2, 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.

Sodium thiomethoxide (28.2 g, 0.403 mol) was suspended in 350 mL of THF and stirred at ambient temperature under a blanket of nitrogen gas while 4,6- dichloropyrimidine (50 g, 0.33 mol) was added. After the addition was completed, the reaction was stirred and heated at 60 0C for 4 hours. The solvent was removed under reduced pressure and the residue was dissolved into 500 mL of 0.25N sodium hydroxide and extracted 3 times with ethyl acetate. The organics were combined and backwashed with water, brine, and 1: 1 brine/lN HCl. The combined organic layer was dried (Na2SO4 anh.) and the solvent was removed under reduced pressure. The crude material was re- crystallized from hot petroleum ether to afford ~24 g of material. LC/MS (M+l): 161.

According to the analysis of related databases, 1193-21-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2009/85913; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
Pyrimidine | C4H4N2 – PubChem,
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;,
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.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;,
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. 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;,
Pyrimidine | C4H4N2 – PubChem,
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