Pyrimidines

Synthetic Route of 39876-88-5, Adding some certain compound to certain chemical reactions, such as: 39876-88-5, name is 4-Chlorobenzofuro[3,2-d]pyrimidine,molecular formula is C10H5ClN2O, 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 39876-88-5.

1-bromo-9H- carbazole (5.0 g, 20.3 mmol) and sodium hydride (1.4 g, 34.5 mmol) were mixed in 200 mL of dry DMF. The solution was stirred for 4 hours and the addition of 4-chlorobenzofuro[3,2-d]pyrimidine(7.9 g, 38.6 mmol). The mixture was refluxed under nitrogen overnight. The reaction mixture was placed in water and the precipitate was then filtered off. After the residue with eluent THF: hexane (1: 1, v / v) was purified by column chromatography using. Of the yellow product was collected 4 .1 g (49%).

According to the analysis of related databases, 39876-88-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Universal Display Corporation; Joseph, Scott; Kwang, Raymond; Lee, Chi Hang; Shia, Chuan Jun; Ram, SiV Cheung; (131 pag.)KR2015/9461; (2015); A;,
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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 1032452-86-0, name is 3-(2-Chloropyrimidin-4-yl)-1-methyl-1H-indole. This compound has unique chemical properties. The synthetic route is as follows. name: 3-(2-Chloropyrimidin-4-yl)-1-methyl-1H-indole

N-(5-amino-4-methoxy-2-(trifluoromethyl)phenyl)acetamide (496 mg, 2.0 mmol),3-(2-chloropyrimidin-4-yl)-1-methyl-1H-indole (704 mg, 4.0 mmol) was dissolved in 2-pentanol (10 mL),Then p-toluenesulfonic acid monohydrate (688 mg, 4.0 mmol) was added.The reaction was stirred at 130 C for 4 hours.After the reaction is over,Cool to room temperatureSaturated sodium bicarbonate (20 mL) was added to the reaction solution.Extract with dichloromethane (100 mL x 3).Combine the organic phase,The organic phase was washed with saturated brine (100 mL).Drying with anhydrous sodium sulfateConcentrate under reduced pressure,The crude product was isolated and purified by silica gel column chromatography (eluent: petroleum ether:Ethyl acetate = 2:1) gave a yellow solid (113 mg, yield: 12.4%).

With the rapid development of chemical substances, we look forward to future research findings about 1032452-86-0.

Reference:
Patent; Tianjin Binjiang Pharmaceutical Research And Development Co., Ltd.; Tian Hongqi; Huang Gongchao; Cheng Ying; (48 pag.)CN107793413; (2018); A;,
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Synthetic Route of 347418-42-2, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 347418-42-2 as follows.

Step 1 To a solution of A16 (25 mg, 0.056 mmol) and 4-chloro-5-fluoropyrimidine (15 mg, 0.11 mmol) in DMSO (0.5 mL) was added CS2CO3 (37 mg, 0.11 mmol) and the mixture was stirred at 15C for 35 mins. The mixture was quenched with water (15 mL) and extracted with EtOAc (4 x 25 mL). The combined organic extracts were washed with brine (10 mL), dried over Na2S04, filtered and concentrated to provide CI as brown oil which was used in the next step without further purification. MS for CI m/e = 540.2 (M+l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,347418-42-2, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WALSH, Shawn, P.; CUMMING, Jared, N.; DAI, Xing; (84 pag.)WO2017/139210; (2017); A1;,
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Related Products of 3435-28-7, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 3435-28-7 as follows.

Example 59: (R)-l-[(6-Methyl-pyrimidin-4-yIcarbamoyI)-methyl]-3-(l-phenyl- cycloheptanecarbonyloxy)-l-azonia-bicyclo[2.2.2]octane chloridea) 2-Chloro-iV-(6-methyl-pyrirnidin-4-yl)-acetamide 6-Methyl-pyrimidin-4-yl amine (545 mg) was suspended in DCE (5 mL) and chloroacetylchloride (0.4 mL) was added dropwise. The reaction was heated in a microwave at 8O0C for 5mins. The reaction mixture was cooled, filtered and a solid obtained. The reaction was repeated a second time and both batches of solid were combined, washed with dichloromethane then suspended in dichloromethane and sat. NaHCO3 (aq.) was added. The organic phase was collected and the aqueous layer extr with dichloromethane (x2). The combined organic layer was dried over sodium sulphc and concentrated. The crude product was purified by silica gel chromatography elutinj with 0-10%MeOH/dichloromethane to give the sub-titled compound as a yellow solid mg).1H NMR (400 MHz, DMSO-D6): delta 11.11 (s, IH), 8.76 (d, IH), 7.91 (s, IH), 4.38 (s, 2 2.44 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3435-28-7, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ARGENTA DISCOVERY LIMITED; WO2009/138707; (2009); A1;,
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Application of 4983-28-2 ,Some common heterocyclic compound, 4983-28-2, molecular formula is C4H3ClN2O, 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 : 2-Chloropyrimidin-5-ol (5.3 g) was dissolved under argon in acetone (144 ml). After addition of potassium carbonate (8.42 g) and 2,2,3,3-tetrafluoropropyl trifluoromethanesulfonate (12.3 g) the mixture was stirred for 18 h. The mixture was diluted with -200 ml ether, stirred for 10 min and filtered. The filtrate was concentrated, taken up in dichloromethane, filtered again and concentrated to dryness to give 2-chloro-5-(2,2,3,3- tetrafluoropropoxy)pyrimidine (8.99g, not totally pure) as orange oil. MS: m/z = 245.0 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4983-28-2, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; DOLENTE, Cosimo; GUBA, Wolfgang; HAAP, Wolfgang; OBST SANDER, Ulrike; PETERS, Jens-Uwe; WOLTERING, Thomas; (99 pag.)WO2016/150785; (2016); 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. 4994-86-9, name is 4-Chloro-2-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

Synthesis of methyl 1-methyl-4-(2-methylpyrimidin-4-yl)-1H-pyrazole-5-carboxylate Using 4-bromo-1-methyl-1H-pyrazole-5-carboxylic acid methyl ester (CAS No.: 514816-42-3, 2.0 g, 9.1 mmol) and 4-chloro-2-methylpyrimidine (0.94 g), methyl 1-methyl-4-(2-methylpyrimidin-4-yl)-1H-pyrazole-5-carboxylate (1.26 g) was obtained as a yellow oily substance using a method similar to that in in Working Example 3 or a method based on this method. (Physical property data) LC-MS: M=232, RT=0.75 (min), [M+H]+=233. 1H-NMR (300 MHz, CDCl3, delta ppm): 8.62 (1H, d, J=5 Hz), 7.85 (1H, s), 7.29 (1H, d, J=5 Hz), 4.15 (3H, s), 3.87 (3H, s), 2.74 (3H, s).

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, 4994-86-9, 4-Chloro-2-methylpyrimidine.

Reference:
Patent; MOCHIDA PHARMACEUTICAL CO., LTD.; SATOH, Tsutomu; KUDOH, Takashi; IWAMA, Tetsuo; (50 pag.)US2017/210740; (2017); A1;,
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Application of 37554-70-4, 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. 37554-70-4, name is 2-Chloro-5-fluoro-4-methoxypyrimidine, molecular formula is C5H4ClFN2O, 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.

(5-Fluoro-4-methoxypyrimidin-2-yl)phenylamine; To a stirred solution of 2-chloro-5-fluoro-4-methoxypyrimidine (16.0 g, 98.8 mmol) and phenylamine (13.8 g, 141.8 mmol) in 1,4-dioxane (500 ml) was added Cs2CO3 (97.8 g, 296.3 mmol) followed by Pd2(dba)3 (2.7 g, 2.9 mmol) and BINAP (3.1 g, 4.9 mmol) under N2. The mixture was heated at reflux for 12 h. On completion, the mixture was filtered to remove the inorganic salts and the filtrate was partitioned between CH2Cl2 (500 ml) and H2O (500 ml). The CH2Cl2 layer was washed with brine (500 ml), dried over NaSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with 5% EtOAc/PE, to afford 13.0 g (63% yield) of the product as a yellow solid.1H NMR (400 MHz, CDCl3) delta 8.07 (d, J = 2.8 Hz, 1H), 7.61 (d, J = 8.0 Hz, 2H), 7.34 (m, 2H), 7.16 (br s, 1H), 7.07 (m, 1H), 4.06 (s, 3H).

According to the analysis of related databases, 37554-70-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wada, Hiroki; Cheng, Lili; Jiang, Ji; Jiang, Zhigan; Xie, Jun; Hu, Tao; Sanganee, Hitesh; Luker, Tim; Tetrahedron Letters; vol. 53; 14; (2012); p. 1720 – 1724;,
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Synthetic Route of 36315-01-2, 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.36315-01-2, name is 2-Amino-4,6-dimethoxypyrimidine, molecular formula is C6H9N3O2, molecular weight is 155.16, as common compound, the synthetic route is as follows.

General procedure: For the synthesis of 2, the solution of sulfurisocyanatidic chloride (7.2mmol) in 20mL toluene was added to the solution of 1 (6.0mmol) in 20mL toluene dropwise at room temperature. The reactant was heated to 140C and then the reaction proceeded for 18h under reflux. Subsequently, the mixture was cooled down to room temperature and remaining sulfurisocyanatidic chloride was removed under reduced pressure, together with the solvent. Without further purification, the resulting yellow oil 2 was dissolved in 10mL anhydrous acetonitrile and after that it was added slowly to 5mmol of 3, which was also dissolved in 10mL anhydrous acetonitrile beforehead in ice bath. After stirring for 24hat room temperature, acetonitrile was removed under reduced pressure and saturated sodium bicarbonate was added to product 4. Product 5 precipitated easily and it was further purified by recrystallization from petroleum ether/acetone in 1:1 ratio in high yields. 15% hydrochloric acid was added to aqueous solution of 5 under stirring and corresponding acidified product 4 precipitated out easily in high yields.

The chemical industry reduces the impact on the environment during synthesis 36315-01-2, I believe this compound will play a more active role in future production and life.

Reference:
Article; Wu, Ren-Jun; Ren, Tongtong; Gao, Jie-Yu; Wang, Li; Yu, Qilin; Yao, Zheng; Song, Guo-Qing; Ruan, Wei-Bin; Niu, Cong-Wei; Song, Fu-Hang; Zhang, Li-Xin; Li, Mingchun; Wang, Jian-Guo; European Journal of Medicinal Chemistry; vol. 162; (2019); p. 348 – 363;,
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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 24415-66-5, name is 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine

Adding 85 mg (about 0.5 mmol) to a 10 mL microwave reaction tube.7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, 198 mg (about 1.5 mmol) of N-methylindole, 14 mg (about 10 mol%) of the catalyst bistrifluoromethylsulfonimide and 1 mL of the solvent HFIP, and then the microwave reaction tube was sealed.Then, the reactant in the microwave reaction tube was stirred at 100 C for 6 hours, and the solvent was distilled off under reduced pressure.And purified by column chromatography using DCM/MeOH as eluent to give about 89 mg of pure product e12 as a yellow solid.67%;

With the rapid development of chemical substances, we look forward to future research findings about 24415-66-5.

Reference:
Patent; Zhengzhou University; Liu Hongmin; Yu Bin; Yuan Shuo; Wang Shuai; Li Zhonghua; (21 pag.)CN109180684; (2019); A;,
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Synthetic Route of 1337532-51-0 , The common heterocyclic compound, 1337532-51-0, name is 5-Bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine, molecular formula is C7H7BrN4, 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.

To a stirred solution of 1-(4-bromo-3-fluorophenyl)-3-(2,5-difluorophenyl)pyrrolidin-2-one (0.3 g, 0.8 mmol, 1.0 equiv ) in 1 ,4-dioxane (20 mL) was added bis(pinacolato)diboron (0.24 g, 1.0 mmol, 1.2 equiv) and potassium carbonate (0.33 g, 2.4 mmol, 3.0 equiv). The reaction mixture was degassed with N2 for 15 minutes, PdCl2(dppf)-CH2Cl2 adduct (0.033 g, 0.04 mmol, 0.05 equiv) was added and the reaction mixture was stirred for 3 hours at 100 C in a sealed tube. The reaction was cooled to room temperature, 5-bromo-7- methyl-7/-/-pyrrolo[2,3-c]pyrimidin-4-amine (0.27 g, 1.2 mmol, 1.5 equiv) and saturated aqueous NaHC03 (10 mL) were added, and N2 gas was bubbled through the mixture for 10 minutes. PdCl2(dppf)-CH2Cl2 adduct (0.033 g, 0.040 mmol, 0.05 equiv) was added, the vessel was sealed, and the reaction mixture was stirred at 100 C for 16 h. The reaction mixture was diluted with water (30 mL) and extracted with ethyl acetate (2 x 20 mL). The organics were combined and dried over Na2S04, filtered, and concentrated in vacuo to get crude compound. Crude product was purified by flash chromatography on silica gel and compound was eluted with 3% MeOH/DCM. The fractions containing the desired product were combined and concentrated to afford 1-4-(4-amino-7-methyl-7/-/-pyrrolo[2,3- d]pyrimidin-5-yl)-3-fluorophenyl)-3-(2,5-difluorophenyl)pyrrolidin-2-one (20 mg, 5.6 %) as off white solid. LCMS (ES) m/z = 438.3 [M+H]+. H NMR (400 MHz, DMSOd6) delta ppm 2.21 – 2.31 (m, 2 H), 3.74 (s, 3 H), 3.97 (t, J=7.6 Hz, 2 H), 4.20 – 4.30 (m, 1 H), 5.98 (br s,2 H), 7.18 – 7.22 (m, 1 H), 7.27 – 7.31 (m, 3 H), 7.39 – 7.45 (m, 1 H), 7.59 (d, J=8.4 Hz, 1 H), 7.81 (d, J=11.6 Hz, 1 H), 8.14 (s, 1 H).

The synthetic route of 1337532-51-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AXTEN, Jeffrey M.; MEDINA, Jesus Raul; WO2015/136463; (2015); A1;,
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