Pyridine-2-carbonitrile → HCID 178437217, compound

Participants

Reaction Steps

0.19 ml triethylamine is added to a solution of 0.22 g 2-(5-piperidin-4H[1,2,4]triazol-3-yl)-pyridine*2HCl (prepared from tert-butyl 4-(hydrazinocarbonyl)piperidine-1-carboxylate and pyridine-2-carbonitrile according to a procedure described in U.S. Pat. No. 4,011,218 or WO2005100344) in 5 ml methanol. To this solution a solution of 0.20 g 4-(3-Ethyl-6-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde in 5 ml DMF is added, followed by 0.09 ml glacial acetic acid and 0.26 g NaBH(OAc)3. The resulting mixture is stirred at room temperature. Additional portions of 2 equivalents NaBH(OAc)3 is added after 1, 2, 3, 5 and 8 hours. The solvent is removed by evaporation after 9 h and the residue is purified by chromatography on silica gel (dichloromethane/methanol) to yield the desired compound.

Provenance & Evidence