Category: pyrimidines

Electric Literature of 42839-08-7, 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.42839-08-7, name is Ethyl pyrimidine-2-carboxylate, molecular formula is C7H8N2O2, molecular weight is 152.15, as common compound, the synthetic route is as follows.

A mixture of ethyl pyrimidin-2-carboxylate (100 gm) and hydrazine hydrate (50 ml in ethanol (500 ml) was stirred at 30 C over a period of 14 h. The suspension was filtered at suction and the wet cake washed with small quantity of ethanol (25 ml) followed by diethyl ether (50 ml) to provide title compound in 80 gm quantity (88%) as a white solid.Mass: m/z: 139.0 (M+l)IH NMR: (400 Mhz, DMSO d6): 4.60 (br s, 2H, exchangeable), 7.64 (t, IH), 8.91 (d, 2H),10.00 (br s, IH, exchangeable)

The chemical industry reduces the impact on the environment during synthesis 42839-08-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; WOCKHARDT RESEARCH CENTRE; TRIVEDI, Bharat Kalidas; PATEL, Mahesh Vithalbhai; WO2010/136971; (2010); A1;,
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Reference of 831203-15-7, 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.831203-15-7, name is 2-(5-Bromopyrimidin-2-yl)acetonitrile, molecular formula is C6H4BrN3, molecular weight is 198.02, as common compound, the synthetic route is as follows.

To a solution of 2-(5-bromopyrimidin-2-yl)acetonitrile (S2, 1 equiv) in DMF/H2O (9:1, 10 vol) was added compound S1 (1 equiv), K2CO3(2 equiv), and tetrakis(triphenylphosphine)palladium (0.1 equiv). The reaction mixture was stirred at 90 C. for 5 h and then concentrated under reduced pressure. The remaining residue was purified by column chromatography on silica gel to give compound S3.

Statistics shows that 831203-15-7 is playing an increasingly important role. we look forward to future research findings about 2-(5-Bromopyrimidin-2-yl)acetonitrile.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAK, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (905 pag.)WO2017/35353; (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. 29133-99-1, name is 4,6-Dichloro-2,5-diphenylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. name: 4,6-Dichloro-2,5-diphenylpyrimidine

General procedure: Intermediate 1-4 (5.0 g, 0.009 mol) in 2-methylpyrimidin-4-ylboronic acid (3.0 g, 0.021 mol), Pd (pph3) 4 (0.5 g, 0.0005 mol), potassium carbonate (2.5 g, into a 110 mL THF to 0.018 mol), on reaction with stirring for 18 hours at 65 It turned on. After the reaction cooled to H20: delamination after column purification (n-Hexane: MC) in MC by Compound 130 to 3.8 g (71%) to give Respectively. Intermediates 33-2 (3.0 g, 0.010 mol) to 4, 6-diphenyl-1, 3, 5-triazin-2-ylboronic acid (3.2 g, 0.012 mol) in the embodiment 1-manufacturing e.g. for inserting and removing (5) the same method used in synthesis of intermediate that is 33-3 3.6g (m/z=497) is obtained (yield 73%)

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Reference:
Patent; PNH TECH; HYUN, SEO YONG; JUNG, SUNG OUK; LEE, RI NA; (142 pag.)KR2015/124637; (2015); A;,
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Synthetic Route of 29509-92-0, 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 29509-92-0, name is 4-Chloro-6-methyl-2-phenylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of 2-(4-bromophenyl)-4-chloro-6-methylpyrimidine (8a, 2.27 g) in acetonitrile (20 mL) was added ethanolamine (2.0 mL), and the mixture was stirred at 70 C for 14 h. To the reaction mixture was added additional ethanolamine (4.0 mL) and the mixture was stirred at 85 C for 6.5 h. The reaction mixture was cooled down to room temperature, and evaporated in vacuo. To the resulting residue was added 1 M aqueous sodium hydroxide (40 mL), and extracted with ethyl acetate. The organic layer was dried, and the desiccant was removed by filtration, and then the solvent was evaporated in vacuo. The resulting residue was purified by silica gel column chromatography (chloroform-methanol) to obtain 9a (2.03 g, 82%) as a white amorphous 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 29509-92-0, 4-Chloro-6-methyl-2-phenylpyrimidine.

Reference:
Article; Negoro, Kenji; Yonetoku, Yasuhiro; Maruyama, Tatsuya; Yoshida, Shigeru; Takeuchi, Makoto; Ohta, Mitsuaki; Bioorganic and Medicinal Chemistry; vol. 20; 7; (2012); p. 2369 – 2375;,
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Related Products of 85386-14-7, 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.85386-14-7, name is Ethyl 2-phenylpyrimidine-5-carboxylate, molecular formula is C13H12N2O2, molecular weight is 228.25, as common compound, the synthetic route is as follows.

To a solution of ethyl 2-phenylpyrimidine-5-carboxylate (4c) (0.080 g, 0.350 mmol) in ethanol(2 mL) was added hydrazine monohydrate 100% (0.351 g, 7.01 mmol). The reaction mixture was stirred at room temperature for 2 h. Ice was added to the reaction flask and the solid, filtered and washed with cold water. The title compound was obtained as a white amorphous solid in 85% yield.

The chemical industry reduces the impact on the environment during synthesis 85386-14-7, I believe this compound will play a more active role in future production and life.

Reference:
Article; Lopes, Alexandra Basilio; Miguez, Eduardo; Kuemmerle, Arthur Eugen; Rumjanek, Victor Marcos; Fraga, Carlos Alberto Manssour; Barreiro, Eliezer J.; Molecules; vol. 18; 10; (2013); p. 11683 – 11704;,
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Adding a certain compound to certain chemical reactions, such as: 26893-39-0, 2-Amino-1,4,5,6-tetrahydropyrimidine Hydrochloride, 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, SDS of cas: 26893-39-0, blongs to pyrimidines compound. SDS of cas: 26893-39-0

3.1. 2-(Pyridin-4-yl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one A mixture of 8.98g (46.5 mmol) of ethyl 3-(4-pyridyl)-3-oxopropionate and 8.0g (46.5 mmol) of 2-amino-3,4,5,6-tetrahydropyrimidine dihydrochloride (prepared according to J. Org. Chem. 1955, 20, 829.) and 19.3g (139.5 mmol) of potassium carbonate in 60ml of ethanol was heated at reflux temperature during 18 h. The solution cooled, was evaporated to remove solvent. The residue was treated with water and extracted with dichloromethane. The extracts were dried and evaporated to give 8.0g (75%) of product as a white powder. Mp: 219 ØC.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,26893-39-0, 2-Amino-1,4,5,6-tetrahydropyrimidine Hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; SANOFI-SYNTHELABO; MITSUBISHI PHARMA CORPORATION; EP1340758; (2003); A1;,
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Synthetic Route of 59864-30-1, 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 59864-30-1, name is 2,6-Dimethoxypyrimidine-4-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of 39b (278 mg, 0.47 mmol) in DMF (5.0 mL) wereadded 4,6-dimethoxypyrimidine-2-carboxylic acid (103 mg,0.56 mmol), DIPEA (160 muL, 0.93 mmol) and HATU (236 mg,0.62 mmol) in an ice-water bath. After stirring at room temperatureovernight, the mixture was quenched with NaHCO3 aq. and extractedwith CHCl3. The organic layer was washed with brine, dried overMgSO4 and concentrated in vacuo. The residue was purified by columnchromatography on silica gel (CHCl3/MeOH/28% NH3 aq.=100:0:0 to90:9:1). EtOAc/IPE was added to the residue, and the resulting precipitatewas filtered and dried. To the precipitate was added EtOH/EtOAc/MeCN, and the mixture was heated to 100 C. After cooling toroom temperature, the resulting precipitate was filtered and dried togive the product (96 mg, 27%) as a colorless solid. 1H NMR (DMSO-d6):delta 0.90 (3H, t, J = 7.2 Hz), 1.46-1.61 (2H, m), 1.74-1.86 (2H, m), 2.14(3H, s), 2.20-2.58 (11H, m), 2.74-2.85 (2H, m), 3.25-3.39 (2H, m),3.67 (3H, s), 4.03 (6H, s), 6.48 (1H, s), 6.82 (1H, d, J = 8.4 Hz),7.16-7.29 (3H, m), 7.51-7.62 (2H, m), 7.77 (1H, dd, J = 7.9, 1.5 Hz),8.13 (1H, s), 8.74-8.87 (1H, m), 9.14 (1H, br s), 9.27 (1H, s), 10.14(1H, br s); MS (ESI) m/z [M+H]+ 762; Anal. Calcd forC36H47N11O6S·1.7H2O: C, 54.56; H, 6.41; N, 19.44; S, 4.05. Found: C,54.55; H, 6.38; N, 19.45; S, 4.02.

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 59864-30-1, 2,6-Dimethoxypyrimidine-4-carboxylic acid.

Reference:
Article; Amano, Yasushi; Echizen, Yuka; Hirano, Masaaki; Hisamichi, Hiroyuki; Iikubo, Kazuhiko; Iwai, Yoshinori; Kameda, Minoru; Kawamoto, Yuichiro; Kikuchi, Shigetoshi; Kondoh, Yutaka; Kuriwaki, Ikumi; Moritomo, Hiroyuki; Noda, Atsushi; Suzuki, Tomoyuki; Tateishi, Yukihiro; Tomiyama, Hiroshi; Bioorganic and medicinal chemistry; (2020);,
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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. 274-71-5, name is Pyrazolo[2,3-a]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of Pyrazolo[2,3-a]pyrimidine

To a solution of pyrazolo[1,5-ajpyrimidine (1 g, 8.39 mmol) in acetonitrile (5 mL) was added NBS (1.494 g, 8.39 mmol) and the reaction mixture stirred at room temperature for 8 h. The reaction mixture was concentrated under reduced pressure and the residue purified by silica gel chromatography (0-30% petroleum ether/EtOAc) to afford 3-bromopyrazolo[1,5-ajpyrimidine (1.2 g, 6.06 mmol, 72% yield) as a brown solid. LCMS (ESI) m/e 198.0 [(M+H), calcd for C6H5BrN3198.01; LC/MS retention time (method A2): tR = 1.43 mm.

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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;,
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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. 149765-15-1, name is N-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropionamide. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 149765-15-1

In a 50 mL round-bottomed flask charged with (2R,3R,4R,5R)-4-(benzyloxy)-5- ((benzyloxy)methyl)-3-fluorotetrahydrofuran-2-ol(0.31 g, 0.94 mmol), N-(4-chloro-7H- pyrrolo[2,3-d]pyrimidin-2-yl)pivalamide (0.26 g, 1.03 mmol) and Ph3P (0.54 g, 2.07 mmol) was added dry THF (5 mL) to give a colorless solution under N2. This was cooled to 0C and then DIAD (0.4 mL, 2.07 mmol) was added dropwise to give a yellow solution. After 20 min, ice- water bath was removed and after stirring for 22 hours, solvent was removed in vacuo. The crude material was purified by Si02 column chromatography eluting from hexanes/EtOAc = 6/1 to 5/1 to 4/1 to afford N-(7-((2R,3R,4R,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-3- fluorotetrahydrofuran-2-yl)-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)pivalamide (0.22 g, 41%) as a white solid. 1H NMR (400 MHz, CDC13) 58.08 (s, 1H), 7.40 – 7.24 (m, 11H), 6.47 (dd, J = 3.8, 0.4 Hz, 1H), 6.26 (dd, J = 19.6, 1.6 Hz, 1H), 5.59 (ddd, J = 53.2, 4.4, 2.0 Hz, 1H), 4.93 (ddd, J = 19.6, 8.0, 4.4 Hz, 1H), 4.83 (d, J= 11.6 Hz, 1H), 4.75 (d, J = 11.6 Hz, 1H), 4.54 (d, J = 11.6 Hz, 1H), 4.49 (d, J= 12.0 Hz, 1H), 4.37 – 4.34 (m, 1H), 3.85 (dd, J= 10.8, 2.4 Hz, 1H), 3.70 (dd, J = 10.8, 4.8 Hz, 1H), 1.33 (d, J= 0.8 Hz, 9H). HRMS C3oH32ClFN404 [M+H+]; calculated: 567.2096, found 567.2180.

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, 149765-15-1, N-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropionamide.

Reference:
Patent; EMORY UNIVERSITY; LIOTTA, Dennis, C.; PAINTER, George, R.; BLUEMLING, Gregory, R.; WO2014/124430; (2014); 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. 87253-62-1, name is 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylic acid

General procedure: In 25ml RB flask to a solution of Compound 9 (200 mg) in dry DMF (5ml), EDCI (250 mg, 1.25eq) and DMAP (130 mg,1eq) were added followed by addition of Sulfonamide (1eq). RM was stirred at RT for 4hrs. Solvent from the reaction mixture was evaporated. To the residue water was added and acidified with 6N HCl, solid precipitated out. Solid was filtered and dried. Crude solid was purified by flash chromatography eluating with 4-8% MeOH/DCM as solvent system to give pure product.

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Reference:
Article; Patil, Vikas; Kale, Manoj; Raichurkar, Anandkumar; Bhaskar, Brahatheeswaran; Prahlad, Dwarakanath; Balganesh, Meenakshi; Nandan, Santosh; Shahul Hameed; Bioorganic and Medicinal Chemistry Letters; vol. 24; 9; (2014); p. 2222 – 2225;,
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