Pyrimidines

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. 90914-41-3, name is 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine. A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine

To a stirred solution of 3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine (3.5 g, 15.02 mmol, 1 equiv) in DMF (60 mL) was added sodium hydride (0.72 g, 18.02 mmol, 1.2 equiv) at 0C. The reaction mixture was stirred for 15 mm at 0C. Methyl iodide (1.12 mL, 18.02 mmol, 1.2 equiv) was added to the reaction mixture at 0C. The reaction mixture was warmed to room temperature and stirred for 3h. The reaction mixture was quenched with ice water and extracted in ethyl acetate. The organic layer was dried over sodium sulphate and evaporated to obtain crude product, which was purified over silica gel flash column chromatography. The compound eluted out in 30% EtOAc in n-Hexane. Fractions obtained were concentrated to give 3-bromo-4-chloro- 1-methyl-i H-pyrazolo[3,4- d]pyrimidine (2.0 g, 57%) as pale yellow solid. LCMS (ES) m/z = 247.4, 249.4 [M+H. ]. 1H NMR (400 MHz, DMSO-d6) O ppm -4.03 (5, 3H), 8.88 (5, 1H)

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Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AXTEN, Jeffrey Michael; FAUCHER, Nicolas Eric; DAUGAN, Alain Claude-Marie; (110 pag.)WO2017/46738; (2017); A1;,
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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. 31169-25-2, name is 7-Bromothieno[3,2-d]pyrimidin-4(3H)-one. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 31169-25-2

Dimethylformamide (25.8 mL, 0.33 mol) and dichloromethane (150 mL) were added to a reactor. Oxalyl chloride (46.4 mL, 0.53 mol) diluted with dichloromethane (150 mL) at room temperature was added to the reactor for about 30 minutes. 7-bromothieno[3,2- d]pyrimidin-4(3H)-one (35 g, 0.15 mol) was added thereto, and then, the reaction solution was heated to reflux for 3 hours. The temperature of the reaction solution was lowered and water was carefully added thereto. The organic layer was separated, and the aqueous layer was subjected to extraction using dichloromethane. The extracted organic layer was dried over anhydrous sodium sulfate. The dried organic layer was filtered and distilled under reduced pressure, and dried with nitrogen gas to obtain the title compound (30.5 g, 85percent). 1H-NMR Spectrum (300 MHz, DMSO-: delta 9.16 (s, 1H), 8.79 (s, 1H)

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Reference:
Patent; HANMI PHARM CO., LTD.; BAE, In Hwan; SON, Jung Beom; HAN, Sang Mi; KWAK, Eun Joo; KIM, Ho Seok; SONG, Ji Young; BYUN, Eun Young; JUN, Seung Ah; AHN, Young Gil; SUH, Kwee Hyun; WO2013/100632; (2013); A1;,
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Synthetic Route of 56844-12-3, 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 56844-12-3, name is 6-Bromo-4-chlorothieno[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 6-Bromo-4-chlorothieno[2,3-d]pyrimidine(5a) (200 mg, 0.802 mmol) was mixed with 1-phenylethanol (2a) (118 mg, 0.962 mmol), Cs2CO3( 313 mg, 0.962 mmol) and acetonitrile (2 mL). The reaction was then stirredunder nitrogen atmosphere at reflux and followed by GC. The mixture was cooledto rt, diluted with EtOAc (40 mL), washed with sat. aq. KHCO3 (20mL), water (2×20 mL) and brine (30 mL). The combined organic fractions weredried over Na2SO4 and concentrated in vacuum. Crudeproduct was absorbed onto Celite 545 and purified by silica gel columnchromatography (n-pentane/EtOAc,6/1). This gave 245 mg (0.730 mmol, 91%) of 6a as an off-white solid.

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 56844-12-3, 6-Bromo-4-chlorothieno[2,3-d]pyrimidine.

Reference:
Article; Han, Jin; Sundby, Eirik; Hoff, Bage H.; Journal of Fluorine Chemistry; vol. 153; (2013); p. 82 – 88;,
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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.1683-75-6, name is 2-Amino-4-chloro-5-fluoropyrimidine, molecular formula is C4H3ClFN3, molecular weight is 147.54, as common compound, the synthetic route is as follows.Formula: C4H3ClFN3

[00306] A mixture of 4-chloro-5-fluoropyrimidin-2-amine (3) (O. lg, 0.64 mmol) and 3,4- dichlorophenyl isocyanate (0.24g, 1.29 mmol) in dioxane (3 mL) was heated overnight at 90 C. The mixture was chromatographed in 0-60% ethyl acetate in hexanes to afford the title product (167). (75mg, 35%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1683-75-6, 2-Amino-4-chloro-5-fluoropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; CURTANA PHARMACEUTICALS, INC.; BEATON, Graham; MCHARDY, Stanton F.; LOPEZ JR., Ambrosio; CAMPOS, Bismarck; WANG, Hua-Yu Leo; (143 pag.)WO2019/169112; (2019); A1;,
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Electric Literature of 1211443-61-6, 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 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.

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.

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 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;,
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Application of 7226-23-5, 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. 7226-23-5, name is 1,3-Dimethyltetrahydropyrimidin-2(1H)-one, molecular formula is C6H12N2O, 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.

A solution of diisopropylamine (344 muL, 2.45 mmol) in dry tetrahydrofuran (2.9 mL) was cooled to -78 C. under nitrogen and then treated with a 2.5M solution of n-butyllithium in hexanes (981 muL, 2.45 mmol). The reaction mixture was stirred at -78 C. for 15 min and then treated dropwise with a solution of (4-morpholin-4-yl-phenyl)-acetic acid methyl ester (549.9 mg, 2.34 mmol) in dry tetrahydrofuran (2 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (1 mL). The resulting reaction mixture was allowed to stir at -78 C. for 30 min, at which time, a solution of iodomethylcyclopentane (540.0 mg, 2.57 mmol) in a small amount of dry tetrahydrofuran was added dropwise. The reaction mixture was then allowed to warm to 25 C. where it was stirred for 67 h. The reaction mixture was quenched with water and then concentrated in vacuo to remove tetrahydrofuran. The aqueous residue was diluted with ethyl acetate (200 mL). The organic phase was washed with a saturated aqueous sodium chloride solution (1*100 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 3/1 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-morpholin-4-yl-phenyl)-propionic acid methyl ester (381.4 mg, 51%) as a white solid: mp 68-70 C.; EI-HRMS m/e calcd for C19H27NO3 (M+) 317.1991, found 317.2001.

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 7226-23-5, 1,3-Dimethyltetrahydropyrimidin-2(1H)-one.

Reference:
Patent; Corbett, Wendy L.; Haynes, Nancy-Ellen; Sarabu, Ramakanth; US2002/2190; (2002); A1;,
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Adding a certain compound to certain chemical reactions, such as: 55583-59-0, 2,5-Diamino-4,6-dichloropyrimidine, 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, Formula: C4H4Cl2N4, blongs to pyrimidines compound. Formula: C4H4Cl2N4

In the reaction vessel, 4,6-dichloropyrimidine-2,5-diamine(500 mg, 2.79 mmol), 3-thienylboronic acid(0.821 g, 6.42 mmol), sodium carbonate(1.48 g, 14.0 mmol), and tetrakis (triphenylphosphine) palladium (0) (162 mg, 0.140 mmol) in toluene (28 mL) in ethanol (7 mL),And distilled water (7 mL) were added at room temperature, and the reaction solution was cooled to room temperature after stirring for 20 hours under heating reflux conditions under an argon atmosphere.Add distilled water (8 mL), stir, separate the aqueous layer with ethyl acetateIt extracted 3 times with (12 mL). After that, combine all organic layers,Saturated aqueous sodium chloride solution (12 mL) is added thereto, and the mixture is stirred for washing, and the separated organic layer is dried over anhydrous sodium sulfate.The filtrate after filtration was concentrated under reduced pressure. The concentrate thus obtained is purified by flash column chromatography (silica gel, n-hexane / ethyl acetate),4,6-di (thiophen-3-yl) pyrimidine-2,5-diamine(0.737 g, 96% yield).

The synthetic route of 55583-59-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Microbial Chemistry Research Foundation; Kumagai, Naoya; Noda, Hidetoshi; Asada, Yasuko; Shibazaki, Masakatsu; (48 pag.)JP2019/64981; (2019); A;,
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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. 7461-50-9, name is 2-Chloropyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

2-Chloropyrimidin-4-ylamine (3.5 g, 27.0 mmol), 4-methoxypiperidine hydrochloride (4.09 g, 27.0 mmol) and Cs2C03 (26.4 g, 81.0 mmol) were suspended in DMF (60 mL) and heated at 120 C for 18 h. The reaction mixture was partitioned between water and EtOAc. The aqueous phase was washed with EtOAc (x 2) and the combined organic phases were washed with brine, dried (MgSO i), and concentrated in vacuo affording the title compound as a solid (2.5 g). The aqueous phase was concentrated in vacuo and the slurry was extracted with EtOAc. The volatiles were removed in vacuo and the resulting residue was purified by chromatography (Si-PCC, gradient 0- 100% EtOAc in cyclohexane) and then triturated with cyclohexane affording a second batch of the title compound (2.38 g, 87% combining the two batches). lH NMR (400 MHz, CDC13) delta: 7.94 (1H, d, J=5.60 Hz), 5.74 (1H, d, J=5.60 Hz), 4.53 (2H s), 4.33-4.24 (2H, m), 3.47-3.37 (4H, m), 3.33-3.24 (2H, m), 1.98-1.87 (2H, m), 1.60-1.47 (2H, m).

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Reference:
Patent; GENENTECH, INC.; BRYAN, Marian C.; CHAN, Bryan; HANAN, Emily; HEFFRON, Timothy; PURKEY, Hans; ELLIOTT, Richard Leonard; HEALD, Robert; KNIGHT, Jamie; LAINCHBURY, Michael; SEWARD, Eileen M.; WO2014/81718; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1074-40-4, 4,6-Dichloro-2-methoxypyrimidine, 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, COA of Formula: C5H4Cl2N2O, blongs to pyrimidines compound. COA of Formula: C5H4Cl2N2O

Step 3. To a solution of 4,6-dichloro-2-methoxy-pyrimidine (0.606 g, 3.38 mmol, Intermediate (4)] and 2-(2,2-difluoro-benzo[l,3]dioxol-5-yl)-ethylamine hydrochloride (0.884 g, 3.72 mmol, Intermediate (62)]) in EtOH (11 mL) is added sodium bicarbonate (0.85 g, 10.14 mmol) and heated to reflux for 4 hours. The reaction mixture is filtered and filtrate is concentrated, residue solid is washed with small amount of EtOH to yield (6-chloro-2-methoxy-pyrimidin-4-yl)-[2-(2.2-difluoro- benzori.31dioxol-5vn-ethyl]-amine [0.918 g, 79%, Intermediate (63)] as a solid. LC/MS: MS: 344 (M+H).

The synthetic route of 1074-40-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AVENTIS PHARMACEUTICALS INC.; WO2006/44732; (2006); A2;,
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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. 876343-10-1, name is 4-Chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below., HPLC of Formula: C6H3ClIN3

4-(3-Hydroxypropyl)benzeneboronic acid (2.51 1 g, 13.95 mmol) and 4-chloro-6-iodo-7H- pyrrolo[2,3-d]pyrimidine (3.44 g, 12.31 mmol) were dissolved in 1 -propanol (100 ml) at RT and an aq. solution of Na2CC>3(2 M) (13.54 ml, 27.1 mmol) was added. Argon was bubbled through the mixture for 5 min and PdCI2(PPh3)2(0.432 g, 0.615 mmol) was added. The RM was stirred at 105C for 22 h and then allowed to cool to RT overnight. The solvent was removed and the residue was sonicated in a mixture of water and THF (3:2). The mixture was filtered, the solids were washed with water and dried to afford the title compound as a solid (2.4 g). Method A: Rt = 0.86 min; [M+H]+= 288.2

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Reference:
Patent; NOVARTIS AG; ARISTA, Luca; HEBACH, Christina; HOLLINGWORTH, Gregory John; HOLZER, Philipp; IMBACH-WEESE, Patricia; LORBER, Julien; MACHAUER, Rainer; SCHMIEDEBERG, Niko; VULPETTI, Anna; ZOLLER, Thomas; (178 pag.)WO2019/186343; (2019); A1;,
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