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. 919116-36-2, name is 4-Chloro-2-(methylthio)-5-(trifluoromethyl)pyrimidine, molecular formula is C6H4ClF3N2S, 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. name: 4-Chloro-2-(methylthio)-5-(trifluoromethyl)pyrimidine
To a solution of 3,5-dimethyl-4-(l-(phenylsulfonyl)-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan- 2-yl)- 1 //-pyrrolo| 2,3-/;|pyridin-6-yl )isoxazole (9.61 g, 20.1 mmol) in degassed 2:1 mixture of dioxane/water (100 mL) was added CS2CO3 (13.06 g, 40.1 mmol), and obtained suspension was degassed for 30 min. 4-Chloro-2-(methylthio)-5-(trifluoromethyl)pyrimidine (US20130017194) (5.04 g, 22.1 mmol) and tetrakis(triphenylphosphine)palladium(0) (2.32 g, 2.01 mmol) were added, and the reaction mixture was stirred at 100 C. After 2 h, another portion of 4-chloro-2- (methylthio)-5-(trifluoromethyl)pyrimidine (1.00 g, 4.38 mmol) was added, and the reaction mixture was heated for another 30 min at 100 C. After cooling down to RT, the mixture was diluted with EtOAc (100 mL) and water (75 mL), and pH was adjusted to pH 8 with sat. aq. NaHC03. Crude product was extracted with EtOAc (3 x 75 mL), combined organic phase was then washed with water (2 x 50 mL) and brine (75 mL), separated, dried over Na2S04, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (EtOAc in hexanes, 0 to 100% gradient) to provide an orange paste, which was then re-purified by reverse phase chromatography (Cl 8, MeCN in aq. 10 mM ammonium formate pH 3.8, 0 to 100% gradient) to give the title compound as a brown solid (2.05 g, 3.76 mmol, 19% yield).
With the rapid development of chemical substances, we look forward to future research findings about 919116-36-2.
Reference:
Patent; SYROS PHARMACEUTICALS, INC.; MARINEAU, Jason J.; CHUAQUI, Claudio; CIBLAT, Stephane; KABRO, Anzhelika; PIRAS, Henri; WHITMORE, Kenneth Matthew; LUND, Kate-Lyn; (200 pag.)WO2019/143719; (2019); A1;,
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