Imidazole → 4-[trans-3-(Tert-butyl-dimethyl-silanyloxy)-cyclopentylamino]-2-methylsulfanyl-pyrimidine-5-carbonitrile

Participants

Reaction Steps

To a mixture of trans-4-(3-hydroxy-cyclopentylamino)-2-methylsulfanyl-pyrimidine-5-carbonitrile (500 mg, 2.0 mmol) in anhydrous DMF (15 mL) was added, at RT, under argon atmosphere, imidazole (680 mg, 10.0 mmol) followed by tert-butyldimethylsilylchloride (750 mg, 5.0 mmol) and the resulting mixture was stirred at RT for 64 h. The reaction mixture was quenched with NH4Cl (sat'd aq, 20 mL) and was extracted with EtOAc (3×20 mL). The combined organic layers were washed with water (2×10 mL), dried over Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (hexane/EtOAc, 95/5) to give 660 mg of 4-[trans-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentylamino]-2-methylsulfanyl-pyrimidine-5-carbonitrile as a white solid.

Provenance & Evidence