Category: 289042-12-2

Synthetic Route of 289042-12-2, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 289042-12-2, name is tert-Butyl 2-((4R,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate. A new synthetic method of this compound is introduced below.

The method for synthesizing the rosuvastatin calcium chiral isomer impurity of the present embodiment comprises the following steps:(1) 20g compound I was added to 500mL three reaction flask, stirred and dissolved in 220mL of acetonitrile was added dropwise 60mL 0.05M hydrochloric acid, the reaction was incubated dropwise at 35 ~ 40 C for 3 hours until the starting material disappeared (TLC: Ester: petroleum ether = 6: 1),The pH was adjusted to neutral with 5% sodium bicarbonate solution, the acetonitrile was removed by distillation under reduced pressure, extracted twice with methylene chloride (100 mL * 2), dried over anhydrous sodium sulfate, filtered,The filtrate was transferred to 500mL three reaction flask, 60g of manganese dioxide was added, the reaction was refluxed for 20 hours, the reaction was over, filtered, the filtrate was evaporated under reduced pressure and concentrated to dryness to give 17.6g light yellow oil, namely compound III, directly into the next reaction; The yield of compound III was 95.2%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,289042-12-2, its application will become more common.

Reference:
Patent; Zhejiang Mei Nuohua Pharmaceutical Chemical Co., Ltd.; Yu Kui; Huang Xiangliang; Jia Jiangnan; Liu Tao; Yu Shenggang; Lin Zufeng; Chen Weiren; Yao Chengzhi; (12 pag.)CN107382875; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 289042-12-2 as follows., 289042-12-2

(2) Preparation of sodium (E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl) amino]pyrimidin-5-yl]-(3R,5S)-3,5-dihydroxy-hept-6-enoate (compound IV) To a 5 L four-necked flask, 2 L (10 mL/g) of acetonitrile and 200 g (1 mol) of tert-butyl 6-[(1E)-2-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methanesulfonyl)amino]-5-pyrimidinyl]vinyl]-2,2-dimethyl-1,3-dioxane-4-acetate (compound III) were added, and stirred to homogeneity, followed by adding 14.8 g (0.02 mol, calculated from titrated content) of an aqueous solution of hydrochloric acid having a mass percentage concentration of 0.06%. The system was warmed up to 35 C. and stirred at the same temperature for 5 hours until compound III was completely consumed. To the reaction system was added dropwise 32.5 g (1.1 mol) of an aqueous solution of sodium hydroxide having a mass percentage concentration of 4%, and stirred at 20 C. for 7 hours until the dihydroxy ester intermediate produced in the first phase was completely consumed. The system was concentrated to remove acetonitrile, followed by adding 2 L (10 mL/g) of purified water, and stirred to clearness. The system was extracted three times with 400 mL (2 mL/g) of methyl tert-butyl ether. The aqueous phase was further concentrated until no organic solvent was left, to give the an aqueous solution of the product, sodium (E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl]-(3R,5S)-3,5-dihydroxy-hept-6-enoate (compound IV), with a purity of >98% and a yield of 97%.

The chemical industry reduces the impact on the environment during synthesis 289042-12-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Asymchem Laboratories (Tianjin) Co., Ltd.; Asymchem Life Science (Tianjin) Co., Ltd.; Tianjin Asymchem Pharmaceutical Co., Ltd.; Asymchem Laboratories (Fuxin) Co., Ltd.; Jilin Asymchem Laboratories Co., Ltd.; HONG, Hao; GAGE, James; LI, Jiuyuan; SHEN, Litao; ZHANG, Lei; DONG, Changming; (12 pag.)US2017/22169; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

289042-12-2, Adding a certain compound to certain chemical reactions, such as: 289042-12-2, tert-Butyl 2-((4R,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate, 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, 289042-12-2, blongs to pyrimidines compound.

BEM (20.0g) was dissolved in acetonitrile (140ml) at 40C, then cooled to 35C beforegradual addition of hydrochloric acid (0.02M, 35ml) at 35C. The resulting solution wasstirred at 35C until the reaction was complete then cooled to 25C. Sodium hydroxide(l.OM, 38ml) was added at 25C and the resulting mixture stirred at this temperature until thereaction was complete. Aqueous hydrochloric acid (1M) was added to adjust the pH of thesolution to pH9. The solution was distilled under reduced pressure (52mBar, <40C) untilapproximately 100ml of acetonitrile/water had been removed. Water (100ml) was added anddistillation continued until a further 100ml of acetonitrile/water had been removed. Theresulting mixture was filtered through a filter pad, the filter washed with water (30ml) and thefiltrates heated to 40C before addition of a solution of calcium chloride dihydrate (3.07g) inwater (29.5ml) over 20min, maintaining the reaction mixture at 38-41C.The reaction mixture was stirred for a further ISmin at 40C, then cooled to 20C and stirredat this temperature for a further 15min. The resulting suspension was filtered, washed withwater (3 x 50ml) and dried to give (?')-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl](3/?,55')-3,5-dihydroxyhept-6-enoic acidcalcium salt (15.8g, 84% yield). These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,289042-12-2, its application will become more common. Reference:
Patent; ASTRAZENECA UK LIMITED; WO2004/108691; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

289042-12-2, Adding some certain compound to certain chemical reactions, such as: 289042-12-2, name is tert-Butyl 2-((4R,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate,molecular formula is C29H40FN3O6S, 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 289042-12-2.

Preparation of LDA: To a 500 mL three-necked flask was added 5.75 g of diisopropylamine and 180 mL of THF, three times with nitrogen, nitrogenGas protection, the temperature to -25 (internal temperature), slowly dropping n-BuLi, keep the internal temperature is not higher than -20 , after the dropTo -10 C, continue stirring for 30min, that is, LDA.A solution of ROS01 (10 g) in tetrahydrofuran (50 mL) was cooled to below -70 C, and freshly prepared bisSolution of lithium isopropylamide in tetrahydrofuran was added dropwise. After stirring for 30 min, 1.6 mL of acetone was slowly added dropwise.60min after the addition of 10mL of acetone, reaction 30min, then add 5mL of acetone, the reaction is completed, add 80mL saturated ammonium chlorideThe solution was quenched, separated, and the tetrahydrofuran phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, evaporated to dryness,The crude product was purified by column chromatography (ethyl acetate: petroleum ether = 4: 1) to give the title compound, 4.93 g, 45% yield.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 289042-12-2.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Zhang Zhenfeng; Chen Zhijun; Liu Daobo; Li Dasheng; (8 pag.)CN104557885; (2017); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia