Water → HCID 59718937, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(2-methylsulfanyl-pyrimidin-4-yl)-1H-benzotriazole (376 mg, 1.5 mmol) in 4 mL of NMP were added N-chlorosuccinamide (250 mg, 1.9 mmol) and 0.5 mL of water. The mixture was placed in an oil bath at 130° C. for 5-10 minutes, cyclohexylamine (450 mg, 5 mmol) was then added and the reaction mixture was stirred in an oil bath at 130° C. for 30 minutes. The cooled reaction mixture was partitioned between water (40 mL) and EtOAc (40 mL). The organic layer was separated and washed twice with water (40 mL), then dried over Na2SO4, filtered and the solvent removed under reduced pressure. The crude residue was purified by flash chromatography and recrystallized from CH2Cl2/EtOAc to give (4-benzotriazol-1-yl-pyrimidin-2-yl)-cyclohexyl-amine as a white short-needle crystalline solid (255 mg, 56% yield). mp=202.0-204.0° C.; MS=295 (M+H)+.

Provenance & Evidence