Pyridine-2-carbonitrile → HCID 178496980, compound

Participants

Reaction Steps

0.36 ml triethylamine is added to a solution of 406 mg 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 15 ml methanol. To this solution a solution of 400 mg methyl 5-(4-formylphenyl)-6-phenylpyrazolo[1,5-a]pyrimidine-2-carboxylate in 15 ml DMF is added, followed by 0.17 ml glacial acetic acid and 473 mg NaBH(OAc)3. The resulting mixture is stirred at room temperature. Additional portions of 2 equivalents NaBH(OAc)3 are added after 1 and 2 hours. The solvent is removed by evaporation after 3 h and the residue is purified by chromatography on silica gel (dichloromethane/[dichloromethane+7M NH3 in methanol]) to yield the desired compound.

Provenance & Evidence