Isopropanol → Ammonia methanol

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(2,2,6,6-tetramethylpiperidin-4-ylamino)-2-chloropyrimidine-5-carbonitrile (72 mg, 0.243 mmol, 1 equiv), 4-cyclopropyl-3-fluoro-5-(1H-tetrazol-1-yl)benzenamine (64 mg, 0.292 mmol, 1.2 equiv), and PTSA monohydrate (37 mg, 0.195 mmol, 0.8 equiv) in IPA (2.5 mL) were heated to 50° C. for 4 hours. After cooling to ambient temperature, the crude mixture was quenched with 2M NH3/MeOH followed by concentrating to dryness and repeating once. The crude product was purified by flash chromatography and eluted with DCM:2M NH3/MeOH=100:0 to 96:4 using 1% 2M NH3/MeOH increments to provide the desired product which was recrystallized with IPA/hexane to give desired compound (61 mg, 53%) as a solid.

Provenance & Evidence