Sodium Cyanide → 4-Cyclopropylpyrimidine-2-carbonitrile

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Reaction Steps

To a solution of diazabicyclooctane (0.013 g, 0.12 mmol) in dimethylsulfoxide and water was added a solution of 2-chloro-4-cyclopropylpyrimidine (0.2 g, 1.2 mmol) in dimethylsulfoxide followed by sodium cyanide (0.066 g, 1.3 mmol). The reaction mixture was stirred at room temperature for 48 h. The mixture was then poured into water and extracted with ethyl acetate, dried over sodium sulfate and concentrated under reduced pressure. The crude compound was purified via flash chromatography (10% ethyl acetate in petroleum ether) to afford 4-cyclopropylpyrimidine-2-carbonitrile (0.14 g, 77%). MS (ES+APCI) (M+H) 146.1; LCMS retention time 3.054 min (Method J).

Provenance & Evidence