Triethylamine → HCID 178437215, compound

Participants

Reaction Steps

A mixture of 142 mg (0.43 mmol) 4-(3-ethyl-6-phenyl-pyrazolo[1,5-a]pyrimidin-5-yl)-benzaldehyde and 314 mg (0.65 mmol, ca 60% pure) 2-(5-azetidin-3-yl-2H-[1,2,4]triazol-3-yl)-6-methyl-pyridine hydrochloride salt in 3.65 mL NMP was treated with 0.146 mL triethylamine and 0.045 mL acetic acid and stirred overnight at rt. The mixture was treated with 101 mg sodium triacetoxyborohydride and stirred overnight at rt. The reaction was partitioned between DCM and saturated sodium hydrogencarbonate solution, the organic phase dried and concentrated in vacuo and the residue purified by preparative reverse phase HPLC to give 49 mg of the title compound contaminated with formic acid.

Provenance & Evidence