Cyanuric acid → 2-Methylpyridine-3-carbonitrile

Participants

Reaction Steps

Cyanuric acid (418 mg, 2.2 mmol) was added in one portion to a suspension of 2-methyl-nicotinamide (intermediate 29) (613 mg, 4.5 mmol) in 2.5 ml of DMF cooled in ice. The reaction was stirred for 2.5 hours then poured into ice. The reaction was extracted with ethyl acetate until the organic layer no longer contained product. The combined organic layers, were dried over Na2SO4, filtered and concentrated. Purified on normal phase chromatography with ethyl acetate/heptane 0 to 50 gradient then 50/50 EA/heptane. Yield (216 mg, 41%). 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 2.78 (s, 3 H), 7.25 (dd, J=7.71, 4.98 Hz, 1 H), 7.89 (dd, J=7.81, 1.56 Hz, 1 H), 8.68 (s, 1 H)

Provenance & Evidence