Hydrogen Peroxide → 4-[5-(4-Fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]butan-1-ol

Participants

Reaction Conditions

Reaction Steps

9-BBN (0.236 g, 0.00193 mol) in tetrahydrofuran (5.00 mL) was treated with 4-but-3-en-1-yl-5-(4-fluorophenyl)thieno[2,3-d]pyrimidine (0.500 g, 0.00176 mol) in tetrahydrofuran (3.0 mL) at 50° C. for 1 h. Ethanol (1.0 mL), 6 N sodium hydroxide (0.33 mL) and 30% hydrogen peroxide (0.67 mL) were then added successively and the resulting mixture was maintained at 50° C. for 1 h. The reaction was then cooled to room temperature, diluted with ethyl acetate (50 mL) and washed with sodium bicarbonate (2×30 mL). The organic layers were combined, concentrated and purified by column chromatography over silica gel (using ethyl acetate/hexane 1:5-1:1 as an eluent) to afford 4-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]butan-1-ol as a white solid in 47% yield.

Provenance & Evidence