Pyridine-2-carbonitrile → HCID 178432372, compound

Participants

Reaction Steps

8.03 ml triethylamine is added to a solution of 9.13 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 150 ml methanol. To this solution a solution of 7.90 g 4-(2-methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzaldehyde in 150 ml DMF is added, followed by 4.14 ml glacial acetic acid and 10.65 g NaBH(OAc)3. The resulting mixture is stirred at room temperature. Five additional portions of 2 equivalents NaBH(OAc)3 are added after 1.5, 2.5, 3.5, 4.5 and 6 hours. The solvent is removed by evaporation after 8 hours and the residue is purified by chromatography on silica gel (dichloromethane/[dichloromethane+7M NH3 in methanol]). The solid residue is suspended in diethylether/methanol (9:1) and stirred at ambient temperature for 18 hours. The desired product is collected by filtration and dried.

Provenance & Evidence