Category: pyrimidines

935534-47-7 , The common heterocyclic compound, 935534-47-7, name is 5-Bromo-4-(trifluoromethyl)pyrimidin-2-amine, molecular formula is C5H3BrF3N3, 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.

[0252] To a dry 50O mL flask was added 5-bromo-4-(trifluoromethyl)-2- pyrimidylamine (10.1 g, 41.7 mmol), potassium acetate (12.3 g, 125.2 mmol), 4,4,5,5- tetramethyl-2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l,3,2-dioxaborolane (11.6 g, 45.9 mmol) and dioxane (15O mL). Argon was bubbled through the solution for 15 minutes, at which time l,l’-bis(diphenylphosphino)ferrocene palladium (H) chloride (1.7 g, 2.1 mmol) was added. The reaction was refluxed in a 115 0C oil bath for 6 hours under argon. After cooling to room temperature, the dioxane was removed in vacuo. EtOAc (500 mL) was added and the resulting slurry was sonicated and filtered. Additional EtOAc (500 mL) was used to wash the solid. The combined organic extracts were concentrated and the crude material was purified by SiO2 chromatography (30-40% EtOAc/hexanes) yielding 4.40 g of an off white solid. By 1H NMR the material was a 1:1 mixture of boronate ester and 2-amino-4-trifluoromethylpyrimidine byproduct. The material was used as is in subsequent Suzuki reactions. LCMS (m/z): 208 (MH+ of boronic acid, deriving from in situ product hydrolysis on LC). 1H NMR (CDCI3): delta 8.72 (s, IH), 5.50 (bs, 2H), 1.34 (s, 12H).

The synthetic route of 935534-47-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; WO2007/84786; (2007); A1;,
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37552-81-1, 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. 37552-81-1, name is 4-Chloro-6-(trifluoromethyl)pyrimidine, molecular formula is C5H2ClF3N2, 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.

4-Chloro-6-trifluoromethylpyrimidine (200 mg, 1.10 mmol) was dissolved in a solution of ammonia in methanol (7 M, 2.4 mL, 16.80 mmol) and then the reaction mixture was heated at 120 C for 5 minutes using microwave irradiation. The mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate (25 mL) and saturated aqueous sodium bicarbonate solution (10 mL). The layers were separated and the organic layer was washed with water (10 mL) and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide 6-(trifluoromethyl)pyrimidin-4-amine. MS ESI calc’d. for C5H5F3N3 [M + H]+ 164, found 164. NMR (500 MHz, DMSOd-6) delta 8.47 (s, 1H), 7.52 (br s, 2H), 6.77 (s, 1H).

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. 37552-81-1, 4-Chloro-6-(trifluoromethyl)pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; ANTHONY, Neville, J.; ANDRESEN, Brian, M.; NORTHRUP, Alan, B.; CHILDERS, Kaleen, K.; DONOFRIO, Anthony; MILLER, Thomas, A.; LIU, Yuan; MACHACEK, Michelle, R.; WOO, Hyun Chong; SPENCER, Kerrie, B.; ELLIS, John Michael; ALTMAN, Michael, D.; ROMEO, Eric, T.; GUAY, Daniel; GRIMM, Jonathan; LEBRUN, Marie-Eve; ROBICHAUD, Joel, S.; WANG, Liping; DUBOIS, Byron; DENG, Qiaolin; WO2014/176210; (2014); A1;,
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85979-59-5, 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 85979-59-5, name is 2-Chloro-4-(4-fluoro-phenyl)-pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a stirred mixture of appropriate alcohol (1.0 mmol) and Cs2CO3 (651 mg, 2.0 mmol) in dimethyl sulphoxide (5 ml) was added appropriate heteroaryl halide (1.2 mmol) and mixture was stirred for 12-16 h at 80 C. The reaction mixture was cooled to room temperature and diluted with water (20 ml). The mixture was extracted with ethyl acetate (2 x 50 ml) and the combined organic extracts were washed with water (2 x 50 ml) and dried over anhydrous sodium sulphate. The solvent was evaporated under reduced pressure and the residue thus obtained was purified by flash silica gel column chromatography using 30-40 % ethyl acetate and petroleum ether as eluent to yield the heteroaryl ethers.

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 85979-59-5, 2-Chloro-4-(4-fluoro-phenyl)-pyrimidine.

Reference:
Article; Das, Sanjib; Harde, Rajendra L.; Shelke, Dnyaneshwar E.; Khairatkar-Joshi, Neelima; Bajpai, Malini; Sapalya, Ratika S.; Surve, Harshada V.; Gudi, Girish S.; Pattem, Rambabu; Behera, Dayanidhi B.; Jadhav, Satyawan B.; Thomas, Abraham; Bioorganic and Medicinal Chemistry Letters; vol. 24; 9; (2014); p. 2073 – 2078;,
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55329-22-1, 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. 55329-22-1, name is 4-Chloro-6-methyl-2-(methylsulfonyl)pyrimidine, molecular formula is C6H7ClN2O2S, 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.

The above synthesis may be carried out as follows: To N-cyanoethylglycine, ethyl ester (15.9 g, 102 mmol) (a compound of formula (Y2)) dissolved in DMSO (70 mL) was added 4-chloro-6-methyl-2-methylsulfonylpyrimidine (18.8 g, 91 mmol) (a compound of formula (Y1)) and diisopropylethylamine (18 mL, 100 mmol). After stirring for 16 hours, the reaction temperature was raised to 70 C. and imidazole (26.5 g, 0.39 mol) was added. After stirring for 1 day, the reaction was cooled to ambient temperature and added to ice water. The solid that formed was suction filtered and collected on paper to give 9.9 g of 2-[(2-cyanoethyl)[2-(1H-imidazol-1-yl)-6-methyl-4-pyrimidinyl]amino]acetic acid, ethyl ester (a compound of formula (Yc1)).

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. 55329-22-1, 4-Chloro-6-methyl-2-(methylsulfonyl)pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Berlex Laboratories, Inc.; Pharmacopeia, Inc.; US6432947; (2002); B1;,
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330785-81-4, 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. 330785-81-4, name is Ethyl 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidine-5-carboxylate, the common compound, a new synthetic route is introduced below.

The product VI obtained in the step (1) is added to 450 ml of ethanol, heated and stirred at 50-55 C until the temperature of the material is cooled to 20-30 C, 105 ml of 10% sodium hydroxide solution is added and stirred at 20-30 C for 1.5-2 hours. The mixture was added dropwise with 10% citric acid solution to adjust the pH of the solution to about 4 ~ 5. A large amount of solid was precipitated and the mixture was stirred at 20-30 C for 1-1.5h. The solid was washed with water and dried under vacuum at 50 C for 3h to obtain 14.0g of white solid. Yield 93.3%.

Statistics shows that 330785-81-4 is playing an increasingly important role. we look forward to future research findings about Ethyl 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidine-5-carboxylate.

Reference:
Patent; Guangzhou Langsheng Pharmaceutical Co., Ltd.; Chen Yuhua; Lu Pingping; Mo Enqing; Zuo Lian; Lu Zhijun; Peng Guizi; Yuan Yongling; (14 pag.)CN104059025; (2017); B;,
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4983-28-2, 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. 4983-28-2, name is 2-Chloro-5-hydroxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of (2R,5R)-tert-butyl 2-(hydroxymethyl)-5-methylmorpholine-4-carboxylate (1.2 g, 5.2 mmol) and 2-chloropyrimidin-5-ol (1 g, 7.5 mmol), DIAD(1.5 g 7.5 mmol) in THF (30 mL) was added triphenylphosphine (2 g, 7.5 mmol) at 0 ¡ãC, then the reaction was stirred at room temperature for 12 hours. The reaction solution was evaporated to dryness and the residue was purified by flash column chromatography, eluting with ethyl acetate: petroleum ether = 1:3 to afford the title compound (0.52 g, 1.52 mmol, 29 percent yield). LCMS Method D RT= 1.54 min, ES+ve 287.9 (M-tBu+H).

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, 4983-28-2, 2-Chloro-5-hydroxypyrimidine.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CASILLAS, Linda N.; HARLING, John David; MIAH, Afjal Hussain; SMITH, Ian Edward David; RACKHAM, Mark David; (204 pag.)WO2017/182418; (2017); A1;,
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13479-88-4 ,Some common heterocyclic compound, 13479-88-4, molecular formula is C5HCl2N3S, 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.

Step 1 5-Chloro-N-(3,4,5-trimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine Procedure: To a stirred solution of 5,7-dichlorothiazolo[5,4-d]pyrimidine (200 mg, 0.97 mmol) and 3,4,5-trimethoxybenzenamine (230 mg, 1.25 mmol) in 7 mL of DMSO was added DIEA (188 mg, 1.45 mmol) in one portion at room temperature. Then the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was poured into 40 mL of water, and the solid obtained was filtered, washed with water (10 mL) to give a crude product. It was purified by silica gel chromatography (silica gel 200-300 mesh, eluting with ethyl acetate) to give 5-chloro-N-(3,4,5-trimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine (337 mg, 98.6%) as a yellow solid. LC-MS: 353.0 [M+H]+, 726.9 [2M+H]+, tR=1.56 min.

According to the analysis of related databases, 13479-88-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hermann, Johannes Cornelius; Lowrie, JR., Lee Edwin; Lucas, Matthew C.; Luk, Kin-Chun Thomas; Padilla, Fernando; Wanner, Jutta; Xie, Wenwei; Zhang, Xiaohu; US2012/252777; (2012); A1;,
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1780-26-3, 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 1780-26-3, name is 2-Methyl-4,6-dichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To 12 ml of 1,4-dioxane, 0.75 g of phenylboronic acid, 1.67 g of potassium carbonate, 0.13 g of dichlorobis (triphenylphosphine) palladium and 1 g of 4,6- dichloro-2-methylpyrimidine were added. This mixture was stirred at 60C for 3 hours and then stirred at 800C for 6 hours. The reaction mixture was left standing to cool to room temperature, poured into an aqueous saturated ammonium chloride solution and then extracted three times with tert- butyl methyl ether. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography to obtain 0.64 g of 4-chloro-2-methyl- 6-phenylpyrimidine.4-chloro-2-methyl-6-rhohenylpyrimidine 1 H-NMR : 2 . 78 ( s , 3H ) , 7 . 49-7 . 56 (m, 4H ) , 8 . 04 -8 . 07 (m, 2H )

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 1780-26-3, 2-Methyl-4,6-dichloropyrimidine.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; MIZUNO, Hajime; WO2010/134478; (2010); A1;,
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908240-50-6, 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. 908240-50-6, name is 2,4-Dichloropyrido[3,4-d]pyrimidine, molecular formula is C7H3Cl2N3, 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.

To the mixture of 2,4-dichloropyrido[3,4-d]pyrimidine (420.00 mg, 2.10 mmol) and 4-(l-(tetrahydro-2H-pyran-2-yl)-lH-pyrazol-4-yl)aniline (408.70 mg, 1.68 mmol) in THF (10.00 mL) was added DIPEA (542.75 mg, 4.20 mmol, 733.45 uL). The mixture was stirred under N2 at 15 ¡ãC for 16 h. TLC (petroleum:EtOAc=0: l, Rf=0.40) showed one new main spot. The reaction mixture was diluted with water (30 mL) and the mixture was extracted with EtOAc (40 mLx3). The combined organic layers were washed dried over Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was purified by recrystallization (petroleum:EtOAc=10: l, 20 mL) to afford the title compound (620.00 mg, 72percent) as a yellow solid. 1H NMR (400 MHz, DMSO-i/6) delta 10.51 (s, 1H), 9.10 (s, 1H), 8.74 (d, J= 6.0 Hz, 1H), 8.45 (d, J= 5.6 Hz, 1H), 8.37 (s, 1H), 7.98 (s, 1H), 7.81 (d, J= 8.4 Hz, 2H), 7.71 (d, J = 8.8 Hz, 2H), 5.43-5.41 (m, 1H), 3.97-3.94 (m, 1H), 3.69-3.62 (m, 1H), 2.15-2.12 (m, 1H), 1.99- 1.94 (m, 2H), 1.72-1.65 (m, 1H), 1.57-1.56 (m, 2H).

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. 908240-50-6, 2,4-Dichloropyrido[3,4-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KADMON CORPORATION, LLC; OLSZEWSKI, Kellen; KIM, Ji-In; POYUROVSKY, Masha; LIU, Kevin; BARSOTTI, Anthony; MORRIS, Koi; (344 pag.)WO2016/210330; (2016); A1;,
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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.171887-03-9, name is N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide, molecular formula is C5H4Cl2N4O, molecular weight is 207.02, as common compound, the synthetic route is as follows.171887-03-9

Example A [00029] Preparation of (1S,4R)-cis-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol hydrochloride salt. [00030] A suspension of (1R,4S)-cis-[4-(hydroxymethyl)-2-cyclopentene-1-yl]carbamic acid, 1, 1-dimethylethyl ester (100 g) in industrial methylated spirit (IMS) (600 ml) was treated with concentrated hydrochloric acid (48 ml, 1.2 molar equivalents) and the resultant solution was heated to the boil over about 0.5 h. Heating under reflux was maintained for about 2.5 h. The solution was cooled to 20 to 25 C. and diluted with IMS (600 ml). Triethylamine (170 ml) was added followed by N-(2-amino-4,6-dichloro-5-pyrimidinyl)formamide (WO95/21161) (97 g). The suspension was heated under reflux for about 17 h to give a clear solution, which was cooled to 25 to 30 C. and finely divided potassium carbonate (169 g) was added. The suspension was stirred in this temperature range for about 0.5 h then cooled to 0 to 5 C. and the solids filtered off. The solids were washed with IMS (3¡Á180 ml and 1¡Á140 ml) and the combined filtrates and washings were concentrated under reduced pressure to a red gum. This was redissolved in IMS (1000 ml) and the solution was concentrated under reduced pressure to a gum. The dilution and re-concentration were repeated twice more, and the final gum was redissolved in IMS (350 ml). [00031] Meanwhile, a mixture of triethylorthoformate (900 ml) and tetrahydrofuran (THF) (400 ml) was prepared and cooled to 0 to 5 C. Concentrated hydrochloric acid (80 ml) was added, maintaininglthe temperature between 0 and 10 C., and more THF (100 ml,) was then added. To this mixture was added the IMS concentrate prepared above, which was rinsed in with IMS (100 ml). The mixture was warmed to 20 to 25 C. and seeded with authentic (1S,4R)-c-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol hydrochloride salt and stirring continued for about 20 h. The slurry was filtered, the solid was washed with a mixture of tert-butyl methyl ether and IMS (9/1, 3¡Á300 ml) and dried in vacuo at 40 to 45 C. to give the title compound (117 g, 82%) as a fawn coloured solid 1H-NMR (DMSO-d6)delta: 8.38(s, 1, purine CH), 7.50(br m, ca 5, NH3+, OH, HOD), 6.20(m, 1, CH) 5.94(m, 1, CH), 5.49(m, 1, NCH), 3.46(m, 2, OCH2), 2.91(br m, 1, CH), 2.70-2.60(m, 1, CH), 1.75-1.66(m, 1, CH).

Statistics shows that 171887-03-9 is playing an increasingly important role. we look forward to future research findings about N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide.

Reference:
Patent; SmithKline Beecham Corporation; US6646125; (2003); B1;,
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