Acetic Acid → HCID 90408896, compound

Participants

Reaction Steps

To a solution of 6-methyl-N4-(pyridin-2-yl)pyridine-3,4-diamine (550 mg, 2.7 mmol) in THF (30 mL) was added acetic acid (0.17 mL, 6.49 mmol) and tert-butyl nitrite (0.54 mL, 4.12 mmol). The reaction was then heated to reflux and stirred overnight. The reaction was concentrated and the residue was purified by chromatography on silica gel (0-10% [2M NH3 in MeOH]CH2Cl2) to give the desired product as a yellow gum (408 mg, 70%). MS (ESI) mass calcd. C11H9N5, 211.09. m/z found, 212.1 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 9.44 (d, J=0.9, 1H), 8.67-8.62 (m, 1H), 8.37 (s, 1H), 8.31-8.23 m, 1H), 8.01-7.96 (m, 1H), 7.41-7.35 (m, 1H), 2.80 (s, 3H).

Provenance & Evidence