N-Hydroxyacetamidine → (4-Benzyl-6-methyl-pyrimidin-2-yl)-[1-(3-methyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yl]-amine

Participants

Reaction Steps

To a solution of 4-(4-benzyl-6-methyl-pyrimidin-2-ylamino)-piperidine-1-carbonitrile (135 mg, 0.44 mmol) and acetamidoxime (39 mg, 0.53 mmol) in EtOAc (1 mL) and THF (1 mL) was added within 10 minutes a solution of zinc chloride (73 mg, 0.53 mmol) in EtOAc (1 mL). After stirring at room temperature for 4 hours the reaction was heated to reflux over night under nitrogen. The reaction was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using CH2Cl2/MeOH 19:1 (v/v) as eluent. The title compound was obtained as a colorless gum (98 mg, 61%).

Provenance & Evidence