Tetrahydrofuran → HCID 59311517, compound

Participants

Reaction Steps

Osmium tetroxide (21 mg) was added to a mixture composed of the above 3-(3-butenyl)-6-di(tert-butoxycarbonyl)amino-4-chloro-1-(4-methoxy-3,5-dimethylpyridin-2-yl)methyl-1H-pyrazolo[3,4-d]pyrimidine (4.78 g), N-methylmorpholine-N-oxide (5.04 g), tetrahydrofuran (60 mL), acetone (60 mL) and water (60 mL), and the mixture was stirred at room temperature for five hours. Ethyl acetate (300 mL) and a 10% sodium thiosulfate solution (500 mL) were added to the reaction mixture, followed by further stirring for 30 minutes. The reaction mixture was separated, and the aqueous layer was extracted with ethyl acetate. Then, the combined organic layers were washed with brine. The organic layers were dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure and the solvent was evaporated to obtain a crude product of the title compound (4.60 g, 91%) as a solid. The resulting compound was directly used for the next reaction without purification.

Provenance & Evidence