1,1'-Carbonyldiimidazole → HCID 178446208, compound

Participants

Reaction Steps

To a solution of N6,N6-dimethyl-3-nitro-N2-(pentan-3-yl)pyridine-2,6-diamine (100 mg, 0.40 mmol) in MeOH (4 mL) was added a catalytic amount of Pd/C. The mixture was purged with hydrogen from a balloon fitted with a needle for 1 h. The resulting mixture was filtered through a pad of celite and concentrated in vacuo. The solid was then dissolved in THF (2 mL) and CDI (100 mg, 1.17 mmol) was added as a solid. After heating for 3 h, the reaction was cooled to room temperature. The excess CDI was quenched by the careful addition of water. The mixture was diluted with EtOAc and washed three times with water and once with brine. The solution was then dried over sodium sulfate, filtered and concentrated in vacuo. Silica gel chromatography (5%-25% EtOAc/hexanes) provided the title compound as a white solid (57 mg, 57%). m/z=249.2 (M+H)+

Provenance & Evidence