Potassium Cyanide → HCID 20773487, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of (S)-1-(5-methanesulfonyloxyhexyl)-8-(N-BOC-aminomethyl)-3-methylxanthine (0.47 g, 1.0 mmol) and potassium cyanide (0.39 g, 6.0 mmol) in dimethylsulfoxide (8.0 ml) was stirred at 60° C. overnight. The reaction was quenched by addition of water (30 ml) and extracted with ethyl acetate (3×15 ml). The combined extracts were washed with water (2×15 ml), saturated aqueous sodium chloride solution (15 ml), dried over magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with 15% methanol-ethyl acetate to give (R)-1-(5-cyanohexyl)-8-(N-BOC-aminomethyl)-3-methylxanthine (0.25 g, 62% yield) as an oil.

Provenance & Evidence