Acetonitrile → HCID 18507610, compound

Participants

Reaction Steps

To a stirred solution of 0.2 ml (3.72 mmol) acetonitrile in 25 ml dry THF under argon at −78° C. was added dropwise 3.3 ml (1,65 mmol) potassium bis(trimethylsilyl)amide solution (0.5M in toluene) and stirring continued for 1 hour. The solution was then transferred dropwise via cannula to a solution of 300 mg (0.75 mmol) 2-amino-4-(5-bromo-furan-2-yl)-6-(2-pyridin-2-yl-ethylsulfanyl)-pyrimidine-5-carbonitrile in 25 ml THF at −78° C. and stirring continued for 5 h at −78° C. and 1 h at −40° C. The reaction mixture was then quenched by addition of saturated aqueous ammonium chloride solution. The mixtured was extracted twice with ethyl acetate and the combined organic phases dried over sodium sulfate and concentrated in vacuo. Chromatography (ethyl acetate/hexane 4/1 then ethyl acetate) afforded 22 mg (8%) 2-amino-4-(5-cyanomethyl-furan-2-yl)-6-(2-pyridin-2-yl-ethylsulfanyl)-pyrimidine-5-carbonitrile as a brown crystalline solid. ES-MS m/e (%): 385 (M+Na+, 45), 363 (M+H+, 100).

Provenance & Evidence