The origin of a common compound about Pyrimidine-4-carboxylic acid

According to the analysis of related databases, 31462-59-6, the application of this compound in the production field has become more and more popular.

Application of 31462-59-6, 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 31462-59-6, name is Pyrimidine-4-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

General Procedure 8 Thionyl chloride (3.55 mL, 48.4 mmol, 3 eq) was added drop-wise to a solution of pyrimidine-4-carboxylic acid (2 g, 16.1 mmol) in EtOH (15 mL) and the resulting mixture was heated to reflux for 14 h. The mixture was then cooled to RT and made alkaline with saturated aqueous NaHCO3 to pH 8. The basic solution was then extracted with EtOAc (450 mL). The combined organic layers were washed with brine (30 mL), dried over Na2SO4, filtered and concentrated in vacuo to afford Intermediate 23 (1.7g, 77%). 1H NMR: (DMSO-d6) delta 9.40 (d, J=1.0 Hz, 1H), 9.10 (d,J=5.1Hz, 1H), 8.05 (dd, J=5.1, 1.3 Hz, 1H), 4.39 (q, J=7.1Hz, 2H), 1.35 (t, J=7.1Hz, 3H); MS: 153 [M+H]+; TLC: 40% hexane in EtOAc: Rf: 0.40.

According to the analysis of related databases, 31462-59-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERSEON CORPORATION; Short, Kevin Michael; Pham, Son Minh; Williams, David Charles; Datta, Somalee; (82 pag.)US2017/326125; (2017); A1;,
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Brief introduction of 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide

The synthetic route of 1211443-61-6 has been constantly updated, and we look forward to future research findings.

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. 1211443-61-6, name is 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide, the common compound, a new synthetic route is introduced below. 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.

The synthetic route of 1211443-61-6 has been constantly updated, and we look forward to future research findings.

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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Some scientific research about 2-(Tributylstannyl)pyrimidine

According to the analysis of related databases, 153435-63-3, the application of this compound in the production field has become more and more popular.

Electric Literature of 153435-63-3, Adding some certain compound to certain chemical reactions, such as: 153435-63-3, name is 2-(Tributylstannyl)pyrimidine,molecular formula is C16H30N2Sn, 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 153435-63-3.

Example 6 4-tert-butyl-7V-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-[2,2′]bipyrimi(iinyl- 4-yl] -benzenesu lfonam ide (Bosentan)To a solution of 13 (3 g, 5 mmol), dry cesium fluoride (1.7 g, 11 mmol) and bis(tri-t-butylphosphine)palladium (0) (255 mg, 0.5 mmol) in dry 1,4-dioxane (60 mL) was added 2-tributylstannyl pyrimidine (2.2 g, 6.0 mmol). The reaction mixture was stirred at 100-110 0C for 16 h under a stream of nitrogen, then cooled to room temperature and filtered through a pad of Celite. The filtrate was concentrated and the resulting residue was purified by column chromatography on silica gel. The title compound (2.23 g, 81 %) was obtained as a pale yellow solid. The crude bosentan was taken up in 6.7 mL of absolute ethanol at reflux. Water (6.7 mL) was added dropwise at reflux. The resulting suspension was allowed to slowly cool to 20-250C. The precipitate was filtered and air-dried at 250C to afford 2.0 g of bosentan monohydrate (70 % yield) as a white solid.1H-RMN (200 MHz, de-DMSO): 1.29 (s, 9H); 3.85 (m, 2H); 3.93 (s, 3H); 4.59 (m, 2H); 6.81-7.18 (m, 4H), 7.43 (d, J = 8.0 Hz, 3H); 8.45 (d, J = 8.0 Hz, 2H); 9.01 (s, 2H) ppm.DSC-TG: endothermic peak at 116.53 0C, with a loss of weight of 3.1 % (monohydrate).D10: 1.36 mum, D50: 20.32 mum, D90: 56.64 mum

According to the analysis of related databases, 153435-63-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INKE, S.A.; RODRIGUEZ ROPERO, Sergio; HUGUET CLOTET, Juan; WO2010/12637; (2010); A1;,
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Extended knowledge of Pyrimidine-2,4-diamine

The chemical industry reduces the impact on the environment during synthesis 156-81-0, I believe this compound will play a more active role in future production and life.

Electric Literature of 156-81-0, 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.156-81-0, name is Pyrimidine-2,4-diamine, molecular formula is C4H6N4, molecular weight is 110.1172, as common compound, the synthetic route is as follows.

To a mixture of 2,4-diaminopyrimidine (5.5 g, 0.05 mol, 1.0 eq.) and THF (200 ml) was added pyridinium tribromide (17.5 g, 0.055 mol, 1.1 eq) at 0 C. in three portions. The resulting mixture was stirred at about 0 C. for two hours, filtered and washed with THF (20 ml). The yellow solid was mixed with water (100 ml) and the resulting mixture was neutralized with 10% NaOH solution to a pH of about 7. Stirring was continued at room temperature for 30 minutes, after which the mixture was filtered, washed with water (2¡Á20 ml) and dried under vacuum at 50 C. to give 8.2 g (87%) of 2,4-diamino-5-bromo-pyrimidine as a white solid. 1H NMR, HPLC and LCMS analyses of this product are identical to the product described in Step 1 of Example 1.

The chemical industry reduces the impact on the environment during synthesis 156-81-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Anadys Pharmaceuticals, Inc.; US2007/117979; (2007); A1;,
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Extended knowledge of 145783-15-9

The synthetic route of 145783-15-9 has been constantly updated, and we look forward to future research findings.

Adding a certain compound to certain chemical reactions, such as: 145783-15-9, 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine, 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, name: 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine, blongs to pyrimidines compound. name: 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine

3) Operation process(1) Add 18L of ethylene glycol and 9.335kg of SM1 to the 100L reactor.12kg SM2 and 16.529kg triethylamine,Stir and mix;(2) heating the reaction solution to 90 ~ 100 C, the reaction liquid solid dissolved, the color is a yellow clear solution; maintaining this temperature for 8 to 10 hours;(3) TLC detection, the developing agent is ethyl acetate: methanol = 1:1, the color developing agent is ninhydrin ethanol solution, and the color is baked at 150 C;Lower the reaction solution to below 50 C,The reaction solution is a dark brown clear solution;The reaction solution was poured into a 200 L reaction vessel containing 50 L of ethyl acetate and 50 L of water under stirring at room temperature;The 100 L reaction kettle was rinsed with 10 L of ethyl acetate and 10 L of purified water.The eluent was poured into a 200 L reaction kettle; stirred at room temperature for 30 minutes; the stirring was stopped, and the layer was allowed to stand.Divide the lower aqueous phase;(4) Add 60 L of purified water to the upper organic phase, stir at room temperature for 30 minutes; stop stirring, let stand for stratification, and separate the lower layer.water box;(5) Transfer the upper organic phase to a 500L reactor and heat to 60-70 C with stirring; in addition, 180 L of isooctane pre-Heat to 60 ~ 70 C, added to the reaction flask;(8) After adding, slowly cool down to room temperature with stirring and firstly cool to 35-45 C (solid precipitation temperature about 30-35 C).Slowly cool down to 20 ~ 30 C; keep stirring at 20 ~ 30 C for 1 hour, and then slowly reduce the temperature to 0 ~ 10 C;(8) stirring at 0 to 10 C for 2 hours;(9) Centrifugal filtration, the reaction kettle and filter cake are mixed with 12 L of ethyl acetate pre-cooled to 0-10 C and 36 L of isooctane.Rinsing(10) The filter cake is dried under vacuum at 45-55 C for 12 to 16 hours to obtain a white powder of Im-1, weighing 11 kg, yield80%.

The synthetic route of 145783-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hebei Kaiwei Pharmaceutical Co., Ltd.; Pang Yuning; (23 pag.)CN108276417; (2018); A;,
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New downstream synthetic route of 2-Methyl-4,6-dichloropyrimidine

With the rapid development of chemical substances, we look forward to future research findings about 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. Formula: C5H4Cl2N2

[0059] Synthesis ofS5: ethyl 2-aminothiazole-5-carboxylate (1.0 g, 5.8 mmol) and 4,6- dichloro-2-methylpyrimidine (0.95 g, 5.8 mmol) were added to an oven dried flask. (0113) Dimethylformamide (20 mL) was then added. The reaction mixture was then cooled to 0 C, and sodium hydride (0.510 g, 12.8 mmol) was added. The reaction was allowed to warm to room temperature and stirred for an additional 3 hours. Excess base was quenched using ammonium chloride. The reaction was then suspended in water and filtered. After drying, the S5 was obtained as a white solid (1.4g, 81% yield). Spectral data: 1H NMR (400 MHz, DMSO-d6) delta 12.30 (s, 1H), 8.07 (s, 1H), 6.88 (s, 1H), 4.24 (q, J = 7.1 Hz, 2H), 2.54 (s, 3H), 1.26 (t, J = 7.1 Hz, 3H); 13C NMR (126 MHz, dmso) delta 167.85, 162.83, 161.96, 159.07, 157.88, 145.84, 122.02, 104.11, 61.22, 25.61,14.70; HRMS-ESI (m/z): [M + H]+ calcd for CnHnClN402S, 299.0364; found 299.0371.

With the rapid development of chemical substances, we look forward to future research findings about 1780-26-3.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; SOELLNER, Matthew, B.; PHADKE, Sameer; MERAJVER, Sofia, D.; (60 pag.)WO2017/87818; (2017); A1;,
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Simple exploration of 127958-10-5

The synthetic route of 127958-10-5 has been constantly updated, and we look forward to future research findings.

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. 127958-10-5, name is 2-Methyl-4-phenylpyrimidine-5-carboxylic acid, the common compound, a new synthetic route is introduced below. Computed Properties of C12H10N2O2

Example 17: To a mixture of A-14 (135 mg, 0.63 mmol), B-1 (150 mg, 0.53 mmol) and DIPEA (273 mu, 1 .60 mmol) in dry ACN (2.0 mL) is added CIP (191 mg, 0.68 mmol) and the mixture is stirred at RT for 2 days. ACN/H20 is added and the mixture is purified by prep. HPLC-MS (using a solvent gradient H20/ACN with NH4OH) to afford 133 mg of Example 17. ESI-MS: 445 [M+Na]+; HPLC (Rt): 1 .04 min (method G).

The synthetic route of 127958-10-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; RIETHER, Doris; FERRARA, Marco; HEINE, Niklas; LESSEL, Uta; NICHOLSON, Janet Rachel; PEKCEC, Anton; SCHEUERER, Stefan; (69 pag.)WO2017/178341; (2017); A1;,
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Some tips on 99586-66-0

According to the analysis of related databases, 99586-66-0, the application of this compound in the production field has become more and more popular.

Electric Literature of 99586-66-0, Adding some certain compound to certain chemical reactions, such as: 99586-66-0, name is 2-Amino-4-chloro-6-methylpyrimidine-5-carbonitrile,molecular formula is C6H5ClN4, 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 99586-66-0.

General procedure: To a solution of 7a (80mg, 0.18mmol, 1 equiv), 4-amino-6-chloropyrimidine-5-carbonitrile (31mg, 0.2mmol, 1.1 equiv) in BuOH was added DIPEA (0.06mL, 0.36mmol, 2 equiv). The mixture was reacted under microwave at 130C for 20min. After completion, the solvent was removed under reduced pressure. The residue was redissolved in CH2Cl2. The crude was further purified via silica gel chromatography to give compound 8a as white solid (81mg, 80%).

According to the analysis of related databases, 99586-66-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wei, Manman; Zhang, Xi; Wang, Xiang; Song, Zilan; Ding, Jian; Meng, Ling-Hua; Zhang, Ao; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 1156 – 1171;,
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Extended knowledge of 6-Chloro-N,N-dimethylpyrimidin-4-amine

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, 31058-83-0, 6-Chloro-N,N-dimethylpyrimidin-4-amine.

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. 31058-83-0, name is 6-Chloro-N,N-dimethylpyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 31058-83-0

Example 33: N.N-Dimethyl-e-KIS.eRVe-tP-iS-methyl-l ^^-oxadiazol-S- l)phenyl]carbonyl}-3,8-diazabicyclo[4.2.0]oct-3-yl]pyrimidin-4-amine.A mixture of Intermediate 12 (50 mg, 0.17 mmol), 2-chloro-4,6- dimethylpyrimidine (24 mg, 0.17 mmol) and DIPEA (0.87 mL, 0.5 mmol) in ACN (1 mL) was heated in the microwave at 200 C for 2 h. The mixture was concentrated in vacuo and chromatography (Hex to 100% EtOAc/Hex) to afford the desired product as a pale yellow foam (39 mg, 55%). MS (ESI) mass calculated for C22H25N7O2, 419.2; m/z found, 420.2. 1 H NMR (500 MHz, CDCI3): 8.15 (s, 1 H), 8.12 – 8.04 (m, 1 H), 7.59 – 7.50 (m, 2H), 7.25 – 7.17 (m, 1 H), 5.22 (s, 1 H), 4.44 – 4.33 (m, 2H), 4.1 1 – 3.99 (m, 1 H), 3.94 – 3.73 (m, 2H), 3.68 – 3.60 (m, 1 H), 3.1 1 – 3.05 (m, 6H), 3.02 – 2.86 (m, 2H), 2.45 – 2.42 (m, 3H), 2.22 – 1 .97 (m, 2H).

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, 31058-83-0, 6-Chloro-N,N-dimethylpyrimidin-4-amine.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50202; (2011); A1;,
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The important role of 105806-13-1

At the same time, in my other blogs, there are other synthetic methods of this type of compound,105806-13-1, 4,6-Dichloro-5-fluoro-2-methylpyrimidine, and friends who are interested can also refer to it.

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.105806-13-1, name is 4,6-Dichloro-5-fluoro-2-methylpyrimidine, molecular formula is C5H3Cl2FN2, molecular weight is 181, as common compound, the synthetic route is as follows.COA of Formula: C5H3Cl2FN2

[00343] To a mixture of 4,6-dichloro-5-fluoro-2-methyl-pyrimidine (390 mg, 2.15 mmol) and diisopropylethylamine (900 mu, 5.17 mmol) in dichloromethane (3.9 mL) was added l-(oxetan-3-yl)piperazine (335 mg, 2.4 mmol) . The mixture was stirred for 10 minutes. The resulting mixture was concentrated in vacuo then purified on a 40 g silica gel cartridge eluting with 0-80% ethyl acetate/heptane to provide 4-chloro- 5-fluoro-2-methyl-6-[4-(oxetan-3-yl)piperazin-l-yl]pyrirnidine (550 mg, 89%). XH NMR (400 MHz, CDC13) delta 5.35 (s, 1H), 4.92 – 4.70 (m, 2H), 4.65 – 4.41 (m, 2H), 4.68 – 4.12 (m, 2H), 2.46 (d, J = 1.1 Hz, 3H), 1.79 (d, J = 0.7 Hz, 3H) ppm. ESI-MS m/z calc. 231.05746, found 232.0 (M+l) +; Retention time: 0.65 minutes.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,105806-13-1, 4,6-Dichloro-5-fluoro-2-methylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; COLLIER, Philip, N.; DAVIES, Robert, J.; DENINNO, Michael, Paul; DOYLE, Elisabeth; FRANTZ, James, Daniel; GOLDMAN, Brian, Anthony; GRILLOT, Anne-Laure; KOLPAK, Adrienne, Lynne; KRAUSS, Raul, Eduardo; LEDFORD, Brian; LIAO, Yusheng; MAGAVI, Sanjay, Shivayogi; MALTAIS, Francois; PEROLA, Emanuele; RYU, Elizabeth, Jin-Sun; SYKEN, Joshua; TANG, Qing; WANG, Tiansheng; (221 pag.)WO2018/106643; (2018); A1;,
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