Methanol → HCID 59311386, compound

Participants

Reaction Steps

Sodium periodate (19 g) was added to a mixture composed of the above di-tert-butyl {4-chloro-3-(2,3-dihydroxypropyl)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl}imidodicarbonate (10 g), tetrahydrofuran (100 ml), methanol (100 ml) and water (100 ml) under cooling in an ice bath, and the mixture was stirred at room temperature for one hour. The reaction mixture was separated with water (600 mL) and ethyl acetate (400 mL). The organic layer was washed with brine, and then dried over anhydrous sodium sulfate and filtered. Then, the filtrate was concentrated under reduced pressure. Methanol (200 mL) was added to the resulting residue. Sodium borohydride (1000 mg) was added under cooling in an ice bath, and the mixture was stirred for one hour. Water (400 ml) was added to the reaction mixture, followed by extraction with ethyl acetate (300 ml) twice. Then, the organic layers were washed with brine. The organic layers were dried over anhydrous sodium sulfate and filtered. Then, the filtrate was concentrated under reduced pressure and the solvent was evaporated to obtain the title compound (8.5 g, 90%) as an oil.

Provenance & Evidence