Tag: M.W=300-400

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 131860-97-4, name is (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate

Toluene (40.8g) was stirred and heated to 700C. Methyl (E)-2-{2-[6-chloropyrimidin-4- yloxy]phenyl}-3-methoxyacrylate (24.2g at 98%w/w, 0.074mols), DABCO (0.85g at 98%w/w, 0.007mols) and 2-cyanophenol (9.9g at 97.5%w/w, O.Odeltamols) were added at 10 minute intervals, maintaining the temperature at 7O0C. After a further 10 minutes DBU , (13.8g at 98%w/w, 0.09mols) was added over 5.5 minutes. During the addition the temperature went up to 78C and cooling was applied to maintain 7O0C. The reaction mixture was stirred at 700C for 90 minutes (still 35.8 area% methyl (E)-2-{2-[6- chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate unreacted by GC analysis). The reaction temperature was raised to 800C and stirring continued for another 90 minutes at which time the reaction was still not complete (14.2 area% methyl (E)-2- {2-[6-chloropyrimidin-4- yloxy]phenyl}-3-methoxyacrylate unreacted by GC analysis). The temperature was raised to 1000C and stirring continued for a further 60 minutes to complete the reaction. The reaction mixture was cooled to 700C before hot water (75C) (78.3g) was added. The mixture was stirred for 15 minutes at 70-75C, then settled and the aqueous phase separated. A second water wash (78.3g) was applied in the same way. The toluene phase (66.6g) contained methyl (J£)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (32.8%w/w), 73.3% of theory.

With the rapid development of chemical substances, we look forward to future research findings about 131860-97-4.

Reference:
Patent; SYNGENTA LIMITED; WO2008/43978; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.1421372-94-2, name is N-(4-Fluoro-2-methoxy-5-nitrophenyl)-4-(1-methyl-1H-indol-3-yl)pyrimidin-2-amine, molecular formula is C20H16FN5O3, molecular weight is 393.3712, as common compound, the synthetic route is as follows.Formula: C20H16FN5O3

3. Synthesis of intermediate 053-5 The intermediate 053-4 (1.2 g, 4.95 mmol) as a raw material was dissolved in 20 mL ofNMP at room temperature in a 50 mL of single-necked flask, followed by adding the intermediate 006-5 (19.5 g, 49.6 mmol) and anhydrous potassium carbonate (2.06 g , 14.9 mmol) into the reaction system. The reaction was heated to 100C and then carried out for 2 h. After the reaction was completed, the reaction was quenched by adding 100 mL of ice water to the mixture. A solid was precipitated, collected, dissolved in 200 mL of methylene chloride and washed once with 100 mL of saturated sodium chloride solution. The organic phases were dried over sodium sulfate and spin-dried to give 1.2 g of the intermediate 053-5 (47%) as a brown solid. LCMS: 518.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1421372-94-2, N-(4-Fluoro-2-methoxy-5-nitrophenyl)-4-(1-methyl-1H-indol-3-yl)pyrimidin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; Shanghai Shaletech Technology Co., Ltd.; JIANG, Yueheng; (143 pag.)EP3216786; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 147118-37-4, name is N-(4-(4-Fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of N-(4-(4-Fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide

Compound IV (10 g) was added to a reaction flask, which was dissolved in tetrahydrofuran (60 mL) and methanol (20 mL), and the mixture was cooled to 5 to 10 C, and sodium borohydride (0.91 g) was added. Stir at 5 C for 2 hours and slowly warm to 25 C. The reaction was quenched by the addition of a saturated ammonium chloride solution and the pH was adjusted to 7-8. 50 mL of ethyl acetate was added, allowed to stand, and the layers were separated. The organic layer and the aqueous layer were separated, and then aqueous layer was extracted with ethyl acetate (60mL). The ethyl acetate extracts and organic layers were combined and washed sequentially with water (40 mL) and brine (aq. The organic layer was dried over anhydrous sodium sulfate.Concentration gave Compound V (9.8 g) in a yield of 98%.

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, 147118-37-4, N-(4-(4-Fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide.

Reference:
Patent; Nanjing Ouxin Pharmaceutical Co., Ltd.; Chen Benshun; Zhou Changyue; (10 pag.)CN108997324; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 330786-24-8 , The common heterocyclic compound, 330786-24-8, name is 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, molecular formula is C17H13N5O, 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.

Intermediate 4 A mixture of about 60.67 g (0.2 mol) of (S) -2- (hydroxymethyl) piperidine-1-carboxylic acid tert-(0.3 mol) was dissolved in 360 mL of THF while 78.698 (0.3 1 01) triphenylphosphine was added. (0.3mol) of diisopropyl azodicarboxylate and 300mL of tetrahydrofuran solution, lh drop complete system slowly warming up to 30 C insulation reaction 24h, the system temperature to 0-5 (: After the reaction was complete, the solvent was evaporated, and 450 mL of methylene chloride (DCM) was added. The mixture was stirred at room temperature for 10 min, filtered, and the filtrate was bubbled with hydrogen chloride gas. The mixture was stirred for 4 h. After the reaction was complete, The organic layer was washed with 5% sodium hydrogencarbonate solution to neutral and then saturated brine, and the organic layer was dried and filtered to dryness to obtain about 62.18 g of intermediate 5 in a yield of 80.45%.

The synthetic route of 330786-24-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Zhongbang Pharmacy Limited Company; Li, Weisi; Huang, Shuang; Wu, Xiaogang; Yang, Jian; Chen, Guoping; Liu, Liping; (14 pag.)CN105859728; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 58536-46-2 ,Some common heterocyclic compound, 58536-46-2, molecular formula is C22H15BrN2, 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.

11.9 g (34 mmol) of 4-(4-bromophenyl)-2,6-diphenylpyrimidine are dissolved in 300 ml of THF and subsequently cooled to -100 C. 22 ml (38 mmol) of a 1.6M solution of n-butyllithium in hexane are slowly added dropwise to the reaction mixture with stirring. The reaction mixture is stirred for 30 min. 200 ml (34 mmol) of a solution of 2-bromo-1,3-diphenyl-2,3-dihydro-1H-benzo-1,3,2-diazaborole in toluene are subsequently added dropwise. The reaction mixture is warmed to 0 C. over a period of 4 h, then 600 ml of ethanol are added dropwise. The precipitated solid is recrystallised from toluene and subsequently sublimed. Yield: 11 g (60% of theory, purity >99.9%).

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. 58536-46-2, 4-(4-Bromophenyl)-2,6-diphenylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck Patent GmbH; Mujica-Fernaud, Teresa; Parham, Amir Hossain; Stoessel, Philipp; Pflumm, Christof; Buesing, Arne; Eberle, Thomas; (30 pag.)US10032992; (2018); B2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 934524-10-4 ,Some common heterocyclic compound, 934524-10-4, molecular formula is C13H9Cl2N3O2S, 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.

General procedure: To a solution of 8 (1 equiv) in n-BuOH (20mL), corresponding amines (1.1 equiv) and N-ethyl-N-isopropylpropan-2-amine (1.2 equiv) were added. The mixture was stirred at 100C for 5h. The mixture was diluted with EtOAc and washed successively with water and brine. The organic layer was dried over Na2SO4, filtered, and evaporated. The resulting intermediate was purified by chromatography.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,934524-10-4, its application will become more common.

Reference:
Article; Wang, Ruifeng; Chen, Yixuan; Zhao, Xiangxin; Yu, Sijia; Yang, Bowen; Wu, Tianxiao; Guo, Jing; Hao, Chenzhou; Zhao, Dongmei; Cheng, Maosheng; European Journal of Medicinal Chemistry; vol. 183; (2019);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 153435-63-3, 2-(Tributylstannyl)pyrimidine, 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: 153435-63-3, blongs to pyrimidines compound. SDS of cas: 153435-63-3

(S)-(5-(((5-chloropyridin-2-yl)amino)methyl)-6-azaspiro[2.5]octan-6-yl)(5-fluoro-2-(pyrimidin-2-yl)phenyl)methanone Intermediates 4 (1 eq) was dissolved dry DMF (20 ml/mmol), then CsF (2 eq), CuI (0.2 eq), [Ph3P]4Pd (0.1 eq) and 2-(tributylstannyl)pyrimidine (1.5 eq; prepared according to Eur. J. Org. Chem. 2003, 1711-1721) was added. The mixture was warmed at 130 C. for 10 minutes (microwave), then poured in aqueous saturated solution of NH4Cl and extracted with AcOEt. The organic layers were combined, dried (Na2SO4) and concentrated under vacuum; crude product was purified by silica gel column chromatography (DCM to DCM/MeOH 9/1) to obtain the title compound with yield of 15%. 1HNMR (CDCl3) delta ppm 8.80-8.93 (m, 1H), 8.64 (d, 1H), 8.24-8.50 (m, 1H), 7.83-8.08 (m, 1H), 6.89-7.40 (m, 4H), 6.17-6.56 (m, 1H), 5.11-5.25 (m, 1H), 4.3-4.9 (m, 1H), 3.6-4.0 (m, 2H), 3.01-3.47 (m, 2H), 1.92-2.38 (m, 1H), 1.45-1.8 (m, 1H), 0.65-1.12 (m, 1H), 0.17-0.59 (m, 4H). ESI+m/z 474 [M+Na]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153435-63-3, 2-(Tributylstannyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ROTTAPHARM S.P.A.; Stasi, Luigi Piero; Rovati, Lucio; US2013/310400; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 150728-12-4, 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 150728-12-4, name is 5-(2-Methoxyphenoxy)-[2,2′-bipyrimidine]-4,6[1H,5H]-dione. This compound has unique chemical properties. The synthetic route is as follows.

5- (2-methoxyphenoxy) -1H- [2,2 ‘] – dipyridyl-4,6-dione (IV) (30 g, 96 mmol)Toluene (400 mL), phosphorus pentachloride (44.0 g, 211.3 mmol) was added and heated to reflux for 2 h. The TLC reaction was complete. (3 mL), and the organic phase was combined, washed with saturated aqueous sodium carbonate solution (100 mL) and saturated brine (100 mL), and the organic phase was washed with water (100 mL) and saturated brine (100 mL) Dried over anhydrous sodium sulfate, and the residue was dried to obtain 29.0 g of the desired product 4,6-dichloro-5- (2-methoxyphenoxy) -2,2 ‘-bipyridine (V) 87%.

According to the analysis of related databases, 150728-12-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Tianci International Pharmaceutical Co., Ltd.; Li Xinjuanzi; Li Jianzhi; Ma Xilai; Chi Wangzhou; Liu Hai; Hu Xuhua; Zheng Xiaoli; Zhai Zhijun; Li Jianxun; (14 pag.)CN104193687; (2017); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 330785-81-4, 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 330785-81-4, name is Ethyl 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

(1) To a suspension of lithium aluminum hydride (4.15 g) in tetrahydrofuran (150 ml) is added a solution of 2-methylthio-4-(3-chloro-4-methoxybenzylamino)-5-ethoxycarbonylpyrimidine (38.32 g) in tetrahydrofuran (100 ml) under ice-cooling at 5 C. to 10 C. over a period of one hour. After the addition, the ice bath is removed, and the reaction mixture is stirred at room temperature for one hour. To the reaction mixture is added water (4.15 ml) under ice-cooling, and thereto is further added 3N aqueous sodium hydroxide solution (4.15 ml). To the mixture is added water (4.15 ml) three times, and the mixture is stirred at room temperature for one hour. The reaction mixture is treated with magnesium sulfate, and the solid precipitates obtained are filtered. The precipitates are washed with tetrahydrofuran. The filtrate and the washings are combined, and concentrated under reduced pressure, and triturated with a mixture of ethyl acetate and isopropyl ether. The resulting crystals are collected by filtration, and washed well with isopropyl ether to give 2-methylthio-4-(3-chloro-4-methoxybenzylamino)-5-hydroxymethylpyrimidine as pale yellow crystalline powder. First production: yield; 25.10 g, m.p. 162-163 C. Second production: yield; 2.32 g, m.p. 159-160 C. In addition, the above solid precipitates are washed again with isopropyl ether, and the filtrate is concentrated under reduced pressure to give colorless crystals. The resulting solid is suspended in isopropyl ether, filtered, and the precipitates are washed well with isopropyl ether and hexane to give 2-methylthio-4-(3-chloro-4-methoxybenzylamino)-5-hydroxymethylpyrimidine (4.26 g) as colorless crystals, m.p. 161-162 C.

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 330785-81-4, Ethyl 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidine-5-carboxylate.

Reference:
Patent; Yamada, Koichiro; Matsuki, Kenji; Omori, Kenji; Kikkawa, Kohei; US2003/32647; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 302964-08-5, Adding some certain compound to certain chemical reactions, such as: 302964-08-5, name is 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide,molecular formula is C16H13Cl2N5OS, 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 302964-08-5.

In a 250 mL two-necked flask equipped with a reflux condenser,Compound I-6 (10.00 g, 25.4 mmol) was added at room temperature,Was dissolved in DMSO, 1-Boc-3-aminopyrrolidine (6.6 g, 35.6 mmol)DIPEA (N, N-diisopropylethylamine), 8.4 mL, 50.8 mmol) was slowly added under a nitrogen stream.Stir for 1 hAnd then heated to 80 C.TLC monitoring reaction. After completion of the reaction, the mixture was cooled to room temperature, water was added thereto, and the mixture was suctioned and washed with ice-cold water and beat with DCM to give a pure white intermediate. The intermediateTransfer to 10 mL of 30% TFA in methylene chloride and the reaction was stirred at room temperature, TLC was monitored, the reaction was completed, steamed to dryness, residualThe residue was washed three times with saturated sodium bicarbonate solution, filtered and the cake was dried to give 7.7% of I-8 in 68% yield.

According to the analysis of related databases, 302964-08-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Sciences Guangzhou Bio-pharmaceutical And Health Institute; Zhang Jiancun; Liu Lu; Chen Chaonan; Duan Anna; Tu Zhengchao; Yao Guoqiang; (42 pag.)CN106749223; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia