Sodium hydride → HCID 25241964, compound

Participants

Reaction Conditions

Reaction Steps

A solution of benzotriazole (2.14 g, 18.03 mmol) in DMF (10 mL) was slowly added at 0° C. to a solution of NaH (60% in mineral oil, 0.850 g, 21.3 mmol) in DMF (20 mL) under nitrogen atmosphere. The reaction mixture was stirred at 0° C. for 15 minutes; a solution of 2,4,5-trichloropyrimidine (3 g, 16.39 mmol) in DMF (20 mL) was then slowly added at 0° C. The reaction mixture was allowed to reach RT while stirring overnight. The solvent was evaporated under reduced pressure; the residue was taken up with EtOAc and washed 3× with water. The aqueous layers were combined and extracted 3 times with EtOAc. The combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure to give a crude oil. This material was purified via flash chromatography (heptane/EtOAc, 8/2) to give 1.5 g (34% yield) of 1-(2,5-dichloro-pyrimidin-4-yl)-1H-benzotriazole.

Provenance & Evidence