Pyrimidine-5-carboxaldehyde → N*3*-(3,5-Dichloro-phenyl)-N*5*-pyrimidin-5-ylmethyl-1H-[1,2,4]triazole-3,5-diamine

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Reaction Steps

A solution of pyrimidine-5-carbaldehyde (54 mg, 0.5 mmol) and N3-(3,5-dichlorophenyl)-1H-1,2,4-triazole-3,5-diamine Intermediate 2 (122 mg, 0.50 mmol) and picolineborane (54 mg, 0.5 mmol) was stirred at rt for 4 hours. The mixture was poured into water (20 mL) and extracted with EtOAc (3×10 mL). The extract was dried with sodium sulfate and the solvent was reduced to 2 mL. The remaining residue was loaded on a 25 g silica gel column and eluted with 5% MeOH in ethyl acetate to give 128 mg (76.2%) of desired product as a white solid. MS +m/z: 335.90 (M+H)+

Provenance & Evidence