Tag: M.W:200-300

Synthetic Route of 114040-06-1 , The common heterocyclic compound, 114040-06-1, name is 3-Bromo-5,7-dichloropyrazolo[1,5-a]pyrimidine, molecular formula is C6H2BrCl2N3, 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 3-bromo-5,7-dichloropyrazolo[l,5-a]pyrimidine (5.0 g, 19 mmol) in DCM (50 mL) was added cyclopropylmethanamine (1.48 g, 21 mmol), and DIPEA (6.6 mL, 38 mmol). The reaction was stirred at rt for 2 h. Water and DCM were added to separate the phases and the aqueous phase was extracted with DCM. The combined organic extracts were dried over NaSC>4, filtered and concentrated. The crude product was purified by flash chromatography (gradient: EtO Ac/hex 0-50%) to give the title compound as a yellow solid (5.25 g, 92%). NMR (400 MHz, CDCl3) delta ppm 7.97 (s, 1H), 6.50 (br. s, 1H), 5.97 (s, 1H), 3.25 (dd, J = 7.3, 5.5 Hz, 2H), 1.26-1.13 (m, 1H), 0.74-0.65 (m, 2H), 0.37 (q, J= 5.0 Hz, 2H); MS ESI [M + H]+ 301.0, calcd for [Ci0Hi0BrClN4 + H]+ 301.0.

The synthetic route of 114040-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY HEALTH NETWORK; LAUFER, Radoslaw; NG, Grace; LI, Sze-Wan; PAULS, Heinz W.; LIU, Yong; PATEL, Narendra Kumar B.; WO2015/70349; (2015); A1;,
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Synthetic Route of 13544-44-0, Adding some certain compound to certain chemical reactions, such as: 13544-44-0, name is 2,4-Dichloro-5-iodopyrimidine,molecular formula is C4HCl2IN2, 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 13544-44-0.

To a solution of 2,4-dichloro-5-iodopyrimidine (27, 8.7 g, 31.6 mmol) and tert-butyl ((4-aminotetrahydro-2H-pyran-4-yl)methyl)carbamate (26, 5 g, 21.7 mmol) in DMAc (200 mL) was added NaHC03 (11.1 g, 132 mmol). After stirring at 80 C for 12 h, the reaction mixture was quenched with water (50 mL) and extracted with EtOAc (300 mL x 3). The combined organic phases were washed with water (200 mL x 2) and brine (100 mL), dried over Na2S04, filtered and concentrated in vacuo. The resulting residue was purified by column chromatography to provide tert-butyl ((4-((2-chloro-5-iodopyrimidin-4-yl)amino)tetrahydro- 2H-pyran-4-yl)methyl) carbamate (28, 5.02 g, 10.7 mmol).

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. 13544-44-0, 2,4-Dichloro-5-iodopyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; G1 THERAPEUTICS, INC.; STRUM, Jay, Copelnad; (156 pag.)WO2018/5863; (2018); 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. 814918-95-1, name is 5-Bromo-4-chlorothieno[2,3-d]pyrimidine, the common compound, a new synthetic route is introduced below. Application In Synthesis of 5-Bromo-4-chlorothieno[2,3-d]pyrimidine

i) 5-bromo-4-[4-(2-pyrrolidin- 1 -ylethoxymethyl)- 1 -piperidyl]thieno[2,3-d]pyrimidine5-Bromo-4-chlorothieno[2,3-d]pyrimidine (828 mg 3.33 mmol) in dry acetonitrile (13 mL) was treated with 4-(2-pyrrolidin- 1 -ylethoxymethyl)piperidine (1.057 g, 5.0 mmol,) and potassium carbonate (687 mg, 5.0 mmol) and heated at 110 C for 30 min in a microwave. The reaction was then poured into ethyl acetate (50 mL) and water (30 mL) and the ethyl acetate layer separated, dried over sodium sulphate and concentrated in vacuum to give 5- bromo-4-[4-(2-pyrrolidin-l -ylethoxymethyl)- l-piperidyl]thieno[2,3-d]pyrimidine (1.322 g, 3.11 mmol, 93%). LCMS RT = 2.91 min. M+l = 427.

The synthetic route of 814918-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; XENTION LIMITED; MADGE, David; CHAN, Fiona; JOHN, Derek Edward; EDWARDS, Simon D.; BLUNT, Richard; HARTZOULAKIS, Basil; BROWN, Lindsay; WO2013/72694; (2013); A1;,
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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. 1211443-61-6, name is 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide, molecular formula is C14H17ClN4O, 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. COA of Formula: C14H17ClN4O

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.

With the rapid development of chemical substances, we look forward to future research findings about 1211443-61-6.

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;,
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Reference of 161489-05-0, 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 161489-05-0, name is 4-Iodo-6-methoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of(S)-4-(difluoromethyl)-N-(6-(3,4-dimethylpiperazin-1- yl)-2,4-difluoro-3 -(1,2,3 ,6-tetrahydropyridin-4-yl)phenyl)-6-oxo- 1 ,6-dihydropyridine- 3-carboxamide (31.5 mg, 0.064 mmol, preparation described in Example 34) and 2- bromo-5-methoxypyrimidine (16.89 mg, 0.089 mmol) in 2-propanol (2.5 mL) at RT was added N,N-diisopropylethylamine (0.022 ml, 0.128 mmol). After heating in a microwave reactor at 170 C for 2 h, the reaction mixture was purified on preparatory column eluting with water (containing 0.1% HCOOH)/acetonitrile (containing 0.1% HCOOH) gradient (85/55). The title compound was isolated as an yellow powder (20 mg, 50%). LCMS [M+1j 602.5.

According to the analysis of related databases, 161489-05-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PROPELLON THERAPEUTICS INC.; AL-AWAR, Rima; ISAAC, Methvin; JOSEPH, Babu; LIU, Yong; MAMAI, Ahmed; PODA, Gennady; SUBRAMANIAN, Pandiaraju; UEHLING, David; WILSON, Brian; ZEPEDA-VELAZQUEZ, Carlos Armando; (311 pag.)WO2019/46944; (2019); A1;,
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Synthetic Route of 145783-15-9 ,Some common heterocyclic compound, 145783-15-9, molecular formula is C7H9Cl2N3S, 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.

23.80 g of 4,6-dichloro-2-propylthio-5-aminopyrimidine was added to the reaction flask.51.7 g of N,N-diisopropylethylenediamine, 9.36 g of cyclopentylamine and 200 ml of DMF,Stir and heat to 90 C, TLC control reaction is complete, cooled to room temperature,The reaction solution was poured into 100 ml of cold water and extracted with ethyl acetate (30 ml ¡Á 3).The organic phase was dried over anhydrous magnesiumYield 24.38 g of a nearly brown solid III-1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,145783-15-9, its application will become more common.

Reference:
Patent; Tianjin Pharmaceutical Institute Co., Ltd.; Liu Bingni; Liu Dengke; Zhi Shuang; Shang Qian; (19 pag.)CN109516990; (2019); A;,
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Electric Literature of 1211443-61-6, Adding some certain compound to certain chemical reactions, such as: 1211443-61-6, name is 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide,molecular formula is C14H17ClN4O, 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 1211443-61-6.

Under nitrogen, 2-chloro-7-cyclopentyl–N,N- dimethyl -7H- pyrrolo [2,3-d] pyrimidine-6-carboxamide (125mg, 0.43mmol), 4-(5 -Amino-pyrazine-2-carbonyl)piperazine-1-carboxylate (150mg, 0.60mmol, cesium carbonate (300mg, 0.92mmol),BINAP (70mg, 0.11mmol), palladium acetate (25mg, 0.11mmol)was dissolved in 1,4-dioxane (35mL) was stirred and heated to 110 , reaction 13h. Completion of the reactionAfter the reaction was cooled to roomtemperature, filtered through Celite, and the filtrate was concentrated underreduced pressure and the solvent was distilled off, the residue was separatedby column chromatography (methylene chloride / methanol (V / V)= 10/1) to give a pale yellow solid (140mg,64.86%)

According to the analysis of related databases, 1211443-61-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; East Sunshine Pharmaceutical Co., Ltd.; Liu, Bing; Zhang, Yingjun; Nie, Linlin; Bai, Shun; Zheng, Changchun; Nie, biao; Li, Zhiyong; Tan, Yumei; (61 pag.)CN105294737; (2016); A;,
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Synthetic Route of 776-53-4, Adding some certain compound to certain chemical reactions, such as: 776-53-4, name is Ethyl 4-amino-2-(methylthio)pyrimidin-5-carboxylate,molecular formula is C8H11N3O2S, 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 776-53-4.

1.2.2 Synthesis of Compound 2 4.12 g (19.3 mmol) of Compound 1 was dissolved in 15 mL of methanol.3 mL of a 0.50 g / mL lithium hydroxide aqueous solution was added dropwise to the reaction solution, and the reaction was performed at 50 C for 5 hours.After the reaction is completed, 30 mL of a saturated ammonium chloride solution is added to the reaction solution to quench the reaction, and the mixture is extracted with ethyl acetate (20 mL ¡Á 3).The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The residue was separated and purified by column (PE / EA, 1: 3) to obtain 3.25 g of a white solid with a yield of 91.0 %

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. 776-53-4, Ethyl 4-amino-2-(methylthio)pyrimidin-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Mudanjiang Normal College; Jing Yunrong; Wei Jicheng; Hao Jingwei; (15 pag.)CN110256445; (2019); A;,
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Adding a certain compound to certain chemical reactions, such as: 13162-26-0, 2,4-Dichloro-6-methyl-5-nitropyrimidine, 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 2,4-Dichloro-6-methyl-5-nitropyrimidine, blongs to pyrimidines compound. Safety of 2,4-Dichloro-6-methyl-5-nitropyrimidine

2,4-Dibenzyloxypyrrolo[3,2-d]pyrimidine was prepared by the method used for the preparation of 2,4-dimethoxypyrrolo[3,2-d]pyrimidine as described in Cupps, T. L., Wise, D. S. and Townsend, L. B. J. Org. Chem., 1983, 48, 1060-1064 and references therein. A solution of sodium benzoxide was prepared by adding sodium (4.5 g) to benzyl alcohol (100 ml) and heating under argon with stirring until all the sodium had reacted. This was added slowly to a solution of 2,4-dichloro-6-methyl-5-nitropyrimidine (17 g) in benzyl alcohol (80 ml). When the exothermic reaction was complete, ether (500 ml) was added and the resulting solution was washed with water, dried (MgSO4), and evaporated, excess benzyl alcohol being removed by distillation under high vacuum. Dimethylformamide dimethyl acetal (25 ml) was added to a solution of the crude residue in dry DMF (100 ml). The resulting solution was heated at 100 C. for 3 h, then evaporated to dryness under high vacuum. The solid residue was triturated with hot ethanol, cooled and filtered to yield 2,4-dibenzyloxy-6-(2-dimethylaminoethenyl)-5-nitropyrimidine as an orange solid (24.5 g). A suspension of this product (20 g) in acetic acid (300 ml) was stirred with zinc dust (30 g), the reaction being cooled in an ice-bath during an exothermic reaction, when the reaction temperature rose to 50 C. The reaction mixture was allowed to attain room temperature for 2 h, and was then filtered, evaporated and partitioned between chloroform and aqueous bicarbonate. The organic phase was washed with water, dried (MgSO4) and evaporated to give 2,4-dibenzyloxypyrrolo[3,2-d]pyrimidine as a solid (15.2 g).

The synthetic route of 13162-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Industrial Research Limited; Albert Einstein College of Medicine of Yesheva University; US6693193; (2004); B1;,
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Application of 35265-83-9, Adding some certain compound to certain chemical reactions, such as: 35265-83-9, name is 2,4-Dichloro-7-methylthieno[3,2-d]pyrimidine,molecular formula is C7H4Cl2N2S, 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 35265-83-9.

Reference Example 35 2-Chloro-7-methyl-4-piperidinoaminothieno[3,2-d] pyrimidine In DMF (N,N-dimethylformamide) was dissolved 700 mg (3.4 mmol) of 2,4-dichloro-7-methylthieno[3,2-d] pyrimidine, and then a solution of 751 mg (7.5 mmol) of 1-aminopiperidine was added dropwise to the resulting solution under ice cooling over 5 minutes. The reaction solution was stirred at 0C. for one hour and then allowed to resume room temperature, followed by stirring for further one hour. After completion of the reaction, ice water was added to the reaction mixture, followed by extraction with ethyl acetate (50 ml*3). After the organic layer was washed successively with 1N hydrochloric acid, water and brine and dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane= 1/8) to give 573 mg (yield: 59.4%) of the title compound. NMR (delta, CDCl3): 1.20-1.28 (1H, m), 1.76-1.91 (5H, m), 2.41 (3H, s), 2.44-2.49 (2H, m), 3.17-3.20 (2H, m), 6.46 (1H, s), 7.46 (1H, s)

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. 35265-83-9, 2,4-Dichloro-7-methylthieno[3,2-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NAKASHIMA, YOSHIHARU; FUJITA, TAKASHI; HIZUKA, MICHIYO; IKAWA, HIROSHI; HIRUMA, TORU; US2001/6969; (2001); A1;,
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