Pyrimidines

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. 6153-44-2, name is Methyl 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate, molecular formula is C6H6N2O4, 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. Quality Control of Methyl 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate

6-morpholin-4-yl-2-pyridin-2-yl-pyrimidine-4-carboxyIic acidMethyl orotate (5 g, 29.41 mmol) was suspended in phosphorous oxychloride (50 ml) and the mixture was heated to reflux for 4 hours. After this time excess phosphorous oxychloride was removed under reduced pressure. The resulting dark residue was poured onto ice with vigorous stirring and the solution was left to stir until all the ice had melted. The crude product was then collected by filtration and the filtrate was extracted with ether (x2). The filtered product was added to the ether washings and dried over magnesium sulfate. The solution was then concentrated to give methyl 2,6-dichloropyrimidine-4- carboxylate (5.25g, 25.37mmol) as a yellow oil that solidified on standing. To this was added morpholine (2.005g, 25.37 mmol) and THF (40ml) and the mixture left for 2 hours at room temperature. The reaction was then evaporated to dryness to afford methyl 2- chloiO-6-morpholin-4-yl-pyrirnidine-4-carboxylate (5.4 Ig, 21 mmol) LCMS Spectrum: MH+ 258.39, Retention time 1.56, Method: Monitor Base Methyl 2-chloro-6-morpholin-4-yl-pyrimidine-4-carboxylate (2.58g, lOmmol), 2- tributylstannyl pyridine (4.055g, 11 mmol) and tetrakis(triphenylphosphine)palladium (0) (1 Omolpercent, lmmol, 1.116g) were suspended in THF (20 ml) and heated to 100 0C for 30 minutes in the microwave. To this mixture was added sodium hydroxide (20 ml) (4M in H2O), and the reaction was stirred for 1 hour. The resulting precipitate was collected by filtration found to be the monosodium salt of 6-morpholin-4-yl-2-pyridin-2-yl-pyrimidine- 4-carboxylic acid, (1.53g). LCMS Spectrum: (M+Na)+ 308.47, Retention Time 1.42, Method: Monitor BaseNMR Spectrum: 1H NMR (300.132 MHz, D2O) 53.70 – 3.86 (m, 8H), 7.11 (s, IH), 7.51 (ddd, IH), 7.94 (td, IH), 8.28 (d, IH), 8.60 (d, IH) ppm.

With the rapid development of chemical substances, we look forward to future research findings about 6153-44-2.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/80382; (2007); 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. 22536-61-4, name is 2-Chloro-5-methylpyrimidine, molecular formula is C5H5ClN2, 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. category: pyrimidines

In a sealed glass tube a suspension of l-cyclopropyl-6-(lH-imidazol-5-yl)-3,3-dimethylindolin- 2-one (example 71a, 70 mg), 2-chloro-5-methylpyrimidine (37.0 mg) and cesium carbonate (158 mg) in acetonitrile (1.05 ml) was heated to 120 C for 30 minutes under microwave irradiation. Then again 18 mg 2-chloro-5-methylpyrimidine and 89 mg cesium carbonate were added and the reaction mixture heated to 120C under conventional heating for 2 hours. The reaction mixture was concentrated in vacuo and purified by flash chromatography (silica gel, gradient, 0% to 100% EtOAc in n-heptane). The title compound was obtained as off white solid (75 mg, 80%). MS (ESI, m/z): 360.2 [(M+H)+].

With the rapid development of chemical substances, we look forward to future research findings about 22536-61-4.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HILPERT, Hans; KOLCZEWSKI, Sabine; LIMBERG, Anja; STOLL, Theodor; WO2015/177110; (2015); A1;,
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Application of 696-82-2 ,Some common heterocyclic compound, 696-82-2, molecular formula is C4HF3N2, 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.

(1) adding 100% of a 2,4-diaminobenzenesulfonic acid solution (18.8 g) to 400 mL of water, stirring Add sodium bicarbonate solid, adjust the pH to 4, slowly warm to 20 C after dissolution, add 13.94 g (99%) 2,4,6-trifluoropyrimidine, control the pH at 4, continue the reaction 2 Hours, the end point of the reaction was detected by thin layer chromatography, and the reaction solution was used after the condensation was completed;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,696-82-2, its application will become more common.

Reference:
Patent; Jiangsu Demeike Chemical Co., Ltd.; Wang Siliang; Wang Xiaojun; (16 pag.)CN108129875; (2018); A;,
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Adding a certain compound to certain chemical reactions, such as: 6299-87-2, 6-Hydroxypyrimidine-4-carboxylic acid, 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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

6-hydroxypyrimidine-4-carboxylic acid 1.00 g (7.14 mmol),30 ml of methylene chloride, 3.60 g (28.4 mmol) of oxalyl chloride and 0.05 g (0.68 mmol) of N, N-dimethylformamide were added to 1.00 g (7.14 mmol), and the mixture was heated under reflux for 3 hours. Then, the reaction solution was concentrated under reduced pressure. To the obtained residue was added 30 ml of methylene chloride, 0.70 g (7.18 mmol) of O-ethylhydroxylammonium chloride and 1.45 g (14.3 mmol) of triethylamine were added under ice cooling, and the mixture was stirred at room temperature for 3 hours . Then, the reaction solution was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography Further purification gave 0.79 g (3.92 mmol, yield 55percent) of 6-chloro-N-ethoxypyridine-4-carboxamide.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6299-87-2, 6-Hydroxypyrimidine-4-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; NIPPON SODA COMPANY LIMITED; ITO, SYUICHI; AMANO, TOMOHIRO; IPPOSHI, JUNJI; KOUBORI, SHINYA; (44 pag.)JP2016/30742; (2016); A;,
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Adding a certain compound to certain chemical reactions, such as: 3167-50-8, 2-Aminopyrimidine-5-carboxylic acid, 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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

To 1.9 g of polyphosphoric acid were added 500 mg (3.59 mmol) of 2-aminopyrimidine-5-carboxylic acid portionwise. It was stirred for 5 mm before 327.6 mg (3.59 mmol) of hydrazinecarbothioamide were added portionwise. It was stirred for 1 h at 140 C. It was allowed to cool down and water was added. The pH was adjusted to 12 by adding 25 vol% aqueous ammonia solution. The precipitate wasfiltered off and washed with water. It was dried under vacuum at 50 C to yield 164 mg (23%) of the title compound, containing ca. 25 mol% of the starting material.?H-NMR (300MHz, DMSO-d6): 6 [ppm]= 7.13 (s, 2H), 7.30 (s, 2H), 8.56 (s, 2H).LC-MS (Method 3): R = 0.44 mm; MS (ESIpos): m/z = 195 [M+H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3167-50-8, 2-Aminopyrimidine-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; THEDE, Kai; BENDER, Eckhard; SCOTT, William; RICHTER, Anja; ZORN, Ludwig; LIU, Ningshu; MOeNNING, Ursula; SIEGEL, Franziska; GOLZ, Stefan; HAeGEBARTH, Andrea; LIENAU, Philip; PUEHLER, Florian; BASTING, Daniel; SCHNEIDER, Dirk; MOeWES, Manfred; GEISLER, Jens; WO2015/140195; (2015); A1;,
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Related Products of 3438-46-8 ,Some common heterocyclic compound, 3438-46-8, molecular formula is C5H6N2, 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.

3-Methyl-pyrimidine [(9. 41] g, 100 mmol), potassium permanganate (26.9 g) and sodium carbonate (10.6 g) was refluxed in water (100 ml) for 72 h followed by filtration through celite. The filtrate was washed with several portions of DCM and EtOAc before acidification with conc. HC1. The formed precipitate was collected and washed with water to yield 1.37 g of the title compound as a white solid. 1H NMR (DMSO-d6) d (ppm): 13.94 (br. s, 1H), 9.37 (d, 1H), 9.07 (d, 1H), 8.01 (dd, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3438-46-8, its application will become more common.

Reference:
Patent; ASTRA ZENECA AB; NPS PHARMACEUTICALS, INC.; WO2004/14881; (2004); A2;,
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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 76196-80-0, name is Methyl 5-methylpyrimidine-2-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Formula: C7H8N2O2

A mixture of methyl 5-methylpyrimidine-2-carboxylate (0.500 g, 3.286 mmol), 1-bromopyrrolidine-2,5-dione (NBS, 0.643 g, 3.615 mmol) and Azobisisobutyronitrile (AIBN, 0.216 g, 1.3 14 mmol) in carbon tetrachloride (4 mL) prepared at the room temperature was heated at reflux for 10 hr, and cooled down to the ambient temperature. Then, water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with aqueous saturated sodium chloride solution, dried with anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was chromatographed (Si02, 12 g cartridge; ethyl acetate / hexane = 0 % to 30 %) to give methyl 5-(bromomethyl)pyrimidine-2-carboxylate as white solid (0.380 g, 50.0%).

With the rapid development of chemical substances, we look forward to future research findings about 76196-80-0.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Jaekwang; HAN, Younghue; KIM, Yuntae; CHOI, Daekyu; MIN, Jaeki; BAE, Miseon; YANG, Hyunmo; KIM, Dohoon; (644 pag.)WO2017/18803; (2017); A1;,
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Application of 330786-24-8, Adding some certain compound to certain chemical reactions, such as: 330786-24-8, name is 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine,molecular formula is C17H13N5O, 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 330786-24-8.

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (120.00 mg, 395.62 mumol) was weighed into a single-mouth flask and anhydrous tetrahydrofuran (10 ml) was added. , triphenylphosphine (311.30 mg, 1.19 mmol), cyclopentanol (34.08 mg, 395.62 mumol), diethyl azodicarboxylate (239.99 mg, 1.19 mmol) were added under argon atmosphere, and the reaction was monitored by TLC at room temperature overnight. complete. The reaction solution was concentrated and column chromatography afforded 117.00 mg of BTK-7 in a yield of 79.62%.

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. 330786-24-8, 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanghai Institute of Technology; Yao Zhiyi; Yang Yan; Xia Xiaoming; Xue Nannan; Shu Qisheng; Wang Qingxuan; Wang Dongsheng; (7 pag.)CN107827892; (2018); A;,
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Pyrimidine – Wikipedia

Reference of 1013916-37-4, 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 1013916-37-4, name is 2-Chloro-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7(8H)-one. This compound has unique chemical properties. The synthetic route is as follows.

To a glass lined vessel was added 2-chloro-8-cyclopentyl-5-methyl-8/-/-pyrido[2,3-c]pyrimidin-7- one (9.35 g, 1.0 equiv.) along with acetonitrile (65 mL, 7.0 vol). N-Bromosuccinimide (9.67 g, 1.5 equiv.) and oxalic acid (0.65 g, 0.2 equiv.) were added. The reaction mixture was heated to 60¡À5 C. The reaction was stirred at 60C until starting material was consumed (at least 6 hours). The slurry was cooled to 20C and H20 (9 mL, 1 vol) was added. To the slurry was added a solution of sodium bisulfite (3.88 g, 1.0 equiv) in H20 (38 mL, 4 vol). The slurry was granulated for 1 hour, then filtered directly onto a 2 Whatman paper filter. The reaction vessel was washed with water (19 mL, 2 vol) followed by a 7:3 mix of methanol/acetonitrile (28 mL, 3 vol), and the washes were transferred onto the filter cake. The product was dried in the vacuum oven at 50-55C. 6-Bromo-2-chloro-8-cyclopentyl-5-methyl-8/-/-pyrido[2,3-c]pyrimidin-7-one (10.52 g; 87%) was isolated as a pale yellow solid.The product was further purified by recrystallization from toluene and n-heptanes. Toluene (60 mL, 6 vol) and 6-bromo-2-chloro-8-cyclopentyl-5-methyl-8/-/-pyrido[2,3-c]pyrimidin- 7-one (10.00 g, 1 equiv) were added to a reaction vessel and heated to 80C. The warm reaction mixture was filtered through an appropriate cartridge to ensure the removal of insoluble Pd and other insoluble contaminants. The filter cartridge was washed with 80C toluene (5 mL, 0.5 vol). The slurry was cooled to 25C at 1 C/min. n-Heptane (70 mL, 7 vol) was added to the reaction slurry at 1 mL/min. The slurry was further cooled to 0C at 1 C/min. The slurry was granulated at 0C for at least 1 hour.The slurry was filtered directly onto a 2 Whatman paper filter. n-Heptane (30 mL, 3 vol) was charged to the reaction vessel and the wash was transferred onto the filter cake and the product was dried in the vacuum oven at 50-55C. 6-Bromo-2-chloro-8-cyclopentyl-5-methyl-8/-/- pyrido[2,3-c]pyrimidin-7-one (8.73 g, 87%) was isolated as a cream colored solid.1H NMR (500 MHz, DMSO-de): delta 9.20 (s, 1 H), 5.82 (m, 1 H), 2.65 (s, 3H), 2.11 (m, 2H), 2.04 (m, 2H), 1.86 (m, 2H), 1.64 (m, 2H);13C NMR (125 MHz, DMSO-cfe): delta 158.2, 158.2, 157.6, 154.1 , 144.0, 120.9, 113.0, 54.4, 28.3, 25.7, 18.3; HRMS: Calcd for dsHuNsOi BnCli (M+H)+: 342.00033, Found: 342.00037.

According to the analysis of related databases, 1013916-37-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; CHEKAL, Brian Patrick; IDE, Nathan D.; WO2014/128588; (2014); A1;,
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Pyrimidine – Wikipedia

Reference of 1152475-42-7, 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. 1152475-42-7, name is 7-Bromo-2-chlorothieno[3,2-d]pyrimidine, molecular formula is C6H2BrClN2S, 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.

7-Bromo-2-chlorothieno[3,2-d]pyrimidine (200 mg, 0.81 mmol) was dissolved in 2-butanol (4 mL) and then potassium carbonate (223 mg, 1.61 mmol) and 3,4,5-trimethoxybenzenamine (110 mg, 0.81 mmol) were added. After blowing nitrogen to the reaction mixture for 10 minutes, Pd2(dba)3 (50 mg, 0.048 mmol) and Xphos (35 mg, 0.073 mmol) were added. The reaction mixture was stirred at 80 C for 2.5 hours and then filtered with celite. The filtrate was diluted with ethyl acetate and washed with brine. The organic layer was dried with magnesium sulfate, filtered with celite, and then concentrated. Purification by chromatography (15% ethyl acetate/hexane) yielded the target compound (120 mg, 43% yield). [0504] 1H NMR (300 MHz, DMSO-d 6) delta 9.42 (s, 1H), 8.33 (s, 1H), 7.85 (s, 1H), 6.65 (s, 2H), 3.76 (s, 6H), 3.60 (s, 3H), MS m/z: 352.45 [M+1].

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 1152475-42-7, 7-Bromo-2-chlorothieno[3,2-d]pyrimidine.

Reference:
Patent; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; SIM, Tae Bo; CHOI, Hwan Geun; HAH, Jung Mi; HAM, Young Jin; JUN, Eun Jin; LEE, Jung Hun; KIM, Hwan; WO2011/49332; (2011); A2;,
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