Benzimidazole → 2-Ethylthio-4-(benzimidazol-1-yl)-5-cyanopyrimidine

Participants

Reaction Steps

To a suspension of sodium hydride (31 mg, 0.78 mmol) in DMF (2.5 mL) at 0° C. was added benzimidazole (86 mg, 0.72 mmol). After stirring for 5 min, the reaction mixture was warmed to room temperature. To this was added 2-ethylthio-4-chloro-5-cyanopyrimidine (130 mg, 0.65 mmol) dissolved in DMF (1.0 mL), then the mixture was heated at 100° C. for 1 h. The reaction mixture was cooled and carefully diluted with H2O. The aqueous layer was extracted with EtOAc several times, and the combined extracts were washed with brine. After drying over Na2SO4, the crude material was purified by flash chromatography using 1:7 acetone:hexane system to give 126 mg of the title compound. Mass spectrum 282.2 (ESI, M+1).

Provenance & Evidence