Sodium Azide → 2-{4-[2-(2-Azidoethyl)cyclopropyl]piperidin-1-yl}-5-chloropyrimidine

Participants

Reaction Conditions

Reaction Steps

2-{2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl 4-methylbenzenesulfonate from step 1 of this example (309 mg, 0.709 mmol) was in 5.67 mL dioxane. NaN3 (106 mg, 1.63 mmol) was added, followed by addition of 1.418 mL water. Reaction mixture was stirred at 100° C. for 2.5 hours before cooled back to room temperature. The reaction mixture was diluted with water and aqueous phase was further extracted with ethyl acetate for 3 times. The combined organic layers were washed with water and brine, then dried over Na2SO4 and concentrated. The residue was purified by column chromatography using gradient elution (0 to 30% ethyl acetate in hexane) to give the titled compound.

Provenance & Evidence