Triethylamine → HCID 68849360, compound

Participants

Reaction Steps

To a stirred solution of the 4-pyrimidin-2-yl-1-({4-[5-(2,2,2-trifluoroethoxy)pyridin-2-yl]piperazin-1-yl}sulfonyl)butan-2-ol (13.7 g, 28.8 mmol) in DCM (250 mL) at 0° C. was added methanesulfonyl chloride (2.68 mL, 34.6 mmol). The reaction was stirred at 0° C. for 20 minutes before dropwise addition of triethylamine (18.1 mL, 129 mmol). Warmed to room temperature and stirred for 16 hours. The reaction mixture was then diluted with DCM (1 L), washed with water (150 mL) and dried (brine, MgSO4), filtered and concentrated in vacuo. The residue was then purified by flash chromatography (silica, 0-5% MeOH in DCM) to give 2-[(3E)-4-({4-[5-(2,2,2-trifluoroethoxy)pyridin-2-yl]piperazin-1-yl}sulfonyl)but-3-en-1-yl]pyrimidine as a yellow solid (11.9 g, 18.6 mmol, 90%).

Provenance & Evidence