Sodium borohydride → 2,2-dimethyl-6-(pyrimidin-4-yl)-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one

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Reaction Steps

To a solution of 2,2-dimethyl-6-[2-(methylsulfonyl)pyrimidin-4-yl]-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one (0.034 g, 0.10 mmol) in ethanol (2 mL) and methanol (15 mL) was added sodium borohydride (0.092 g, 2.4 mmol) in four portions over 20 min, and the reaction was stirred at room temperature for 15 h. Then, the reaction mixture was concentrated, the residue was dissolved in water (15 mL), and the solution was extracted with 75:25 ethyl acetate/tetrahydrofuran (2×40 mL). The combined organic layers were washed with brine (30 mL), dried over magnesium sulfate, filtered, and concentrated, and the residue was purified by flash chromatography (silica gel, ethyl acetate to 90:10 ethyl acetate/methanol) to give the title compound (0.012 g, 46%) as a yellow solid:

Provenance & Evidence