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. 7461-50-9, name is 2-Chloropyrimidin-4-amine, molecular formula is C4H4ClN3, 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. Application In Synthesis of 2-Chloropyrimidin-4-amine

To a solution of sodium hydride (0.817 g, 34.1 mmol) in Tetrahydrofuran (THF) (30 mL) at room temperature was added a solution of (R)-(2,2-dimethyl-l,3-dioxolan-4- yl)methanol (3 g, 22.70 mmol) in THF (5 mL) over 1 min and stirred at room temperature for 15 min then add 2-chloropyrimidin-4-amine (2.059 g, 15.89 mmol) portion wise at room temperature. The reaction mixture was stirred at 65 C for 16h. The reaction mixture was poured in to water and extracted with EtOAc (3 X lOOmL). Then the combined organic layer was washed with water, brine solution, dried over sodium sulfate and evaporated to get 4.0 g of crude compound. The crude compound was purified by column chromatography using 100-200 silica gel mesh and eluted with 2-3% MeOH/DCM to get pure compound (2.5g, 10.42 mmol, 46%), LCMS (m/z) 226.2 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 7461-50-9.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ELLIS, James Lamond; EVANS, Karen Anderson; FOX, Ryan Michael; MILLER, William Henry; SEEFELD, Mark Andrew; (766 pag.)WO2016/79709; (2016); A1;,
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Synthetic Route of 776-53-4, Adding some certain compound to certain chemical reactions, such as: 776-53-4, name is Ethyl 4-amino-2-(methylthio)pyrimidin-5-carboxylate,molecular formula is C8H11N3O2S, 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 776-53-4.

1.2.2 Synthesis of Compound 2 4.12 g (19.3 mmol) of Compound 1 was dissolved in 15 mL of methanol.3 mL of a 0.50 g / mL lithium hydroxide aqueous solution was added dropwise to the reaction solution, and the reaction was performed at 50 C for 5 hours.After the reaction is completed, 30 mL of a saturated ammonium chloride solution is added to the reaction solution to quench the reaction, and the mixture is extracted with ethyl acetate (20 mL ¡Á 3).The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The residue was separated and purified by column (PE / EA, 1: 3) to obtain 3.25 g of a white solid with a yield of 91.0 %

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. 776-53-4, Ethyl 4-amino-2-(methylthio)pyrimidin-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Mudanjiang Normal College; Jing Yunrong; Wei Jicheng; Hao Jingwei; (15 pag.)CN110256445; (2019); A;,
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Electric Literature of 1211443-61-6, Adding some certain compound to certain chemical reactions, such as: 1211443-61-6, name is 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide,molecular formula is C14H17ClN4O, 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 1211443-61-6.

Under nitrogen, 2-chloro-7-cyclopentyl–N,N- dimethyl -7H- pyrrolo [2,3-d] pyrimidine-6-carboxamide (125mg, 0.43mmol), 4-(5 -Amino-pyrazine-2-carbonyl)piperazine-1-carboxylate (150mg, 0.60mmol, cesium carbonate (300mg, 0.92mmol),BINAP (70mg, 0.11mmol), palladium acetate (25mg, 0.11mmol)was dissolved in 1,4-dioxane (35mL) was stirred and heated to 110 , reaction 13h. Completion of the reactionAfter the reaction was cooled to roomtemperature, filtered through Celite, and the filtrate was concentrated underreduced pressure and the solvent was distilled off, the residue was separatedby column chromatography (methylene chloride / methanol (V / V)= 10/1) to give a pale yellow solid (140mg,64.86%)

According to the analysis of related databases, 1211443-61-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; East Sunshine Pharmaceutical Co., Ltd.; Liu, Bing; Zhang, Yingjun; Nie, Linlin; Bai, Shun; Zheng, Changchun; Nie, biao; Li, Zhiyong; Tan, Yumei; (61 pag.)CN105294737; (2016); A;,
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Synthetic Route of 145783-15-9 ,Some common heterocyclic compound, 145783-15-9, molecular formula is C7H9Cl2N3S, 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.

23.80 g of 4,6-dichloro-2-propylthio-5-aminopyrimidine was added to the reaction flask.51.7 g of N,N-diisopropylethylenediamine, 9.36 g of cyclopentylamine and 200 ml of DMF,Stir and heat to 90 C, TLC control reaction is complete, cooled to room temperature,The reaction solution was poured into 100 ml of cold water and extracted with ethyl acetate (30 ml ¡Á 3).The organic phase was dried over anhydrous magnesiumYield 24.38 g of a nearly brown solid III-1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,145783-15-9, its application will become more common.

Reference:
Patent; Tianjin Pharmaceutical Institute Co., Ltd.; Liu Bingni; Liu Dengke; Zhi Shuang; Shang Qian; (19 pag.)CN109516990; (2019); A;,
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Electric Literature of 274693-26-4, 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 274693-26-4, name is 2-(((3aR,4S,6R,6aS)-6-(7-(((1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanol. This compound has unique chemical properties. The synthetic route is as follows.

To a reaction mixture of 7.7 g (0.01368 moles) 2-[[(3aR,4S,6R,6aS)-6-[7-[[(1 R,2S)-2-(3,4- difluorophenyl)cyclopropyl]amino]-5-(propylthio)-3H-1 ,2,3-triazolo[4,5-d]pyrimidin-3-yl]-2,2- dimethyltetrahydro-3aH-cyclopenta[d][1 ,3]dioxol-4-yl]oxy]-1-ethanol of formula VII in 15 ml methanol, 15 ml concentrated hydrochloric acid was charged and the reaction mixture was stirred at room temperature for 2-3 hours. The reaction mixture was cooled to 0C to 5C and neutralized with 30 ml aqueous ammonia and extracted two times with 25 ml ethyl acetate, ethyl acetate layers were combined and washed with 25 ml water. Ethyl acetate layer was distilled under reduced pressure at 40C. Ticagrelor was isolated from 20% acetone in heptane mixture and dried under vacuum at 45C to 50C. Yield = 5.36g (Efficiency – 75%, HPLC -99.4%).

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 274693-26-4, 2-(((3aR,4S,6R,6aS)-6-(7-(((1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanol.

Reference:
Patent; CIPLA LIMITED; COTTRILL, Emily; RAO, Dharmaraj Ramachandra; MALHOTRA, Geena; PHULL, Manjinder Singh; GHAGARE, Maruti; (34 pag.)WO2016/30704; (2016); A1;,
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Related Products of 696-82-2, 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 696-82-2, name is 2,4,6-Trifluoropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

(According to the process of prior German Patent Application P 39 00 471 (O.Z. 0050/40474)) At -20 C. and over a period of 45 minutes, 335.8 g (1.865 mol) of 30% strength sodium methylate (in methanol) was added to a mixture of 250 g (1.865 mol) of 2,4,6-trifluoropyrimidine, and the mixture was stirred for a further 30 minutes at this temperature. The temperature was then allowed to rise to 25 C., and the reaction mixture was evaporated down to about one fifth of its volume. The mixture obtained was partitioned between diethyl ether and water, after which the organic phase was dried over magnesium sulfate and evaporated down. Distillation (1.1 meter column, 3 mm V-shaped packings) gave 141.6 g (52% of theory) of the title compound of boiling point 144-145 C. Distillation of the residue through a fractionating column (from Normag) gave 114.4 g (42% of theory) of 4,6-difluoro-2-methoxypyrimidine of boiling point 157-161 C.

According to the analysis of related databases, 696-82-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASF Aktiengesellschaft; US5276007; (1994); A;,
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Pyrimidine – Wikipedia

Application of 187035-79-6, 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 187035-79-6, name is Ethyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

(S)-(2-(8-(hydroxymethyl)-1-isopropyl-7-(methylsulfonyl)-3,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrazin-2(1H)-yl)-4-(trifluoromethyl)pyrimidin-5-yl)methanol To a solution of (R)-methyl 1-isopropyl-7-(methylsulfonyl)-1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazine-8-carboxylate (80 mg, 0.228 mmol) in iPrOH (2 mL) and DCM (1 mL) was added ethyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate (174 mg, 0.684 mmol) and DIEA (177 mg, 1.37 mmol). The mixture was stirred at 60 C. overnight. Water (5 mL) was added to the mixture and the aqueous layer was extracted with EtOAc (2*10 mL). The combined organic layers were washed with water (2*10 mL) and brine, dried over anhydrous Na2SO4, filtered and concentrated under vacuum. The residue was purified by preparative TLC to afford (R)-methyl 2-(5-(ethoxycarbonyl)-4-(trifluoromethyl)pyrimidin-2-yl)-1-isopropyl-7-(methylsulfonyl)-1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazine-8-carboxylate (75 mg, 57.8% yield) as a yellow solid.

According to the analysis of related databases, 187035-79-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Vitae Pharmaceuticals, Inc.; Gregg, Richard E.; US2015/250787; (2015); A1;,
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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. 31462-54-1, name is 2-Iodopyrimidine, the common compound, a new synthetic route is introduced below. SDS of cas: 31462-54-1

Compound 2 obtained in the manner described above (200 mg, 0.971 mmoles), 2,5-thiophene diborate (Wako Pure Chemical Industries, Ltd.) (501 mg, 2.91 mmoles), sodium carbonate (Wako Pure Chemical Industries, Ltd.) (309 mg, 2.91 mmoles) and tetrakis (triphenylphosphine) palladium (0) (Wako Pure Chemical Industries, Ltd.) (33.7 mg, 0.0292 mmoles) were dissolved in a mixed solvent containing 10 ml of toluene and 10 ml of methanol. Air was removed to create a vacuum and the space was purged with nitrogen three times after which the reaction mixture was agitated for thirty minutes at 60C. After letting the reaction solution stand until cooled, Compound 1 obtained in the manner described above was added. The air was removed to create a vacuum and the space was purged with nitrogen three times again after which the reaction mixture was agitated for four hours at 60C. After allowing the reaction solution to cool, the reaction solution was diluted with ethyl acetate, washed once using de-ionized water, and once using an aqueous saturated sodium chloride solution. The organic layer was dried using anhydrous sodium sulfate. The solvent was removed by distillation, and the product was purified using a medium pressure fractionating liquid chromatography to obtain yellow solids (Compound 5) (191 mg, 0.453 mmoles, 47%). The analytical results for the Compound 5 synthesized {N,N-dihexyl-4-[5-(pyrimidine-2-yl) thiophene-2-yl] aniline} are shown below. 1H-NMR (400 MHz, CDCl3, TMS, rt) delta 8.67 (2H, d, J = 4.9 Hz), 7.92 (1H, d, J = 3.9 Hz), 7.53 (2H, brd, J = 8.8 Hz), 7.18 (1H, d, J = 3.8 Hz), 7.03 (1H, t, J = 4.9 Hz), 6.64 (2H, brd, J = 8.8 Hz), 3.29 (4H, t, J = 7.7 Hz), 1.60 (4H, brs), 1.33 (12H, brs), 0.91 (6H, t, J = 6.5 Hz)

The synthetic route of 31462-54-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; National University Corporation Hokkaido University; EP2395055; (2011); A1;,
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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. 2434-53-9, name is 6-Amino-1-methylpyrimidine-2,4(1H,3H)-dione, the common compound, a new synthetic route is introduced below. SDS of cas: 2434-53-9

General procedure: A mixture of isatin (0.147 g, 1 mmol), acetophenone (0.09 mL, 1.5 mmol), and piperidine (two drops, 0.1 mmol) in ethanol (95.5%, 1 mL) was heated at 80 C for about 5 min. To the solid obtained at this stage was added 6-amino-1,3-dimethyluracil (0.155 g, 1 mmol), p-toluenesulfonic acid monohydrate (0.076 g, 0.04 mmol), and EtOH (95.5%, 2 mL). The mixture was stirred and heated gently at 80 C. After completion of the reaction (115 min), as monitored by TLC using 5:1 ratio of ethyl acetate/n-hexane, the reaction mixture was cooled to room temperature and then filtered. The separated solids were washed twice with 10 mL of water and 3 mL of hot ethanol (95.5%) to obtain the pure product 4a.

The synthetic route of 2434-53-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rad-Moghadam, Kurosh; Azimi, Seyyedeh Cobra; Tetrahedron; vol. 68; 47; (2012); p. 9706 – 9712;,
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Synthetic Route of 26032-72-4 ,Some common heterocyclic compound, 26032-72-4, molecular formula is C10H6Cl2N2, 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.

[00240] To a solution of 2,4-dichloro-6-phenylpyrimidine (1.52 g, 6.7 mmol) and (¡À)-trans-methyl 3-aminobicyclo[2.2.2]octane-2-carboxylate (1.84 g, 10.0 mmol) inN,N-dimethylformamide (10 mL) was added potassium carbonate (0.92 g, 6.7 mmol). The mixture was stirred at rt overnight. After the reaction was completed, the mixture was diluted with H20 (50 mL), and the resulting mixture mixture was extracted with ethyl acetate (40 mL x3). The combined organic layers were washed with saturated brine (50 mL), dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (n-hexane/EtOAc (v/v) = 20/1 – 10/1) to give the title compound as a white solid (1.65 g, 66%).MS (ESI, pos.ion) m/z: 372.2 [M+H]+1H NMR (400 MHz, CDC13) (ppm): 8.04-7.91 (m, 2H), 7.5 1-7.41 (m, 3H), 6.78 (s, 1H), 5.41 (s, 1H), 4.32 (s, 1H), 3.73 (s, 3H), 2.38 (d, J= 5.1 Hz, 1H), 2.07 (s, 1H), 1.86 (m, 1H), 1.73 (m, 1H),1.70-1.60 (m, 4H), 1.57 (m, 2H), 1.5 1-1.41 (m, 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. 26032-72-4, 2,4-Dichloro-6-phenylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; REN, Qingyun; TANG, Changhua; LIN, Xiaohong; YIN, Junjun; YI, Kai; (270 pag.)WO2017/97234; (2017); A1;,
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