Pyridine-2-carbonitrile → HCID 178430919, compound

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Reaction Steps

0.36 ml triethylamine is added to a solution of 0.41 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 10 ml methanol. To this solution a solution of 0.35 g 4-(3-methyl-6-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde in 10 ml DMF is added, followed by 0.17 ml glacial acetic acid and 0.48 g NaBH(OAc)3. The resulting mixture is stirred at room temperature. Additional portions of 2 equivalents NaBH(OAc)3 are added after 1, 2, 4, 5, 8 and 24 hours. The solvent is removed by evaporation after 27 h and the residue is purified by chromatography on silica gel (dichloromethane/[dichloromethane+7M NH3 in methanol]) to yield the desired compound, witch is precipitated by the addition of methanol.

Provenance & Evidence