Hydrogen Peroxide → 3-(5,7-Dichloropyrazolo[1,5-a]pyrimidin-6-yl)propan-1-ol

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Reaction Steps

A mixed solution was prepared by adding dropwise a borane-dimethyl sulfide complex (20.3 mL, 40.7 mmol) to a tetrahydrofuran (85 mL) solution containing 6-allyl-5,7-dichloropyrazolo[1,5-a]pyrimidine (5.8 g, 25.4 nmol) at 0° C. over 30 min while strring. After flrther stirring at room temperature for 1 hr, the mixed solution was cooled to 0° C. The mixed solution was treated with 1 N aqueous solution of sodium hydroxide (40 mL, 40 mmol) and subsequently with aqueous hydrogen peroxide solution (30% aqueous solution, 3 nm), and the resulting solution was stirred at room temperature for 1 hr. After extracting the mixture solution with ethyl acetate, the organic layer was washed with saturated aqueous solution of sodium chloride, and then dried with sodium sulfate. After drying, sodium sulfate was filtered off and the solvent was removed under vacuum. The residue was purified by column chromatography (25-50% ethyl acetate/hexane) to obtain the title compound (3.4 g, yield: 55%).

Provenance & Evidence