1,1'-Carbonyldiimidazole → HCID 59242074, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of N-methyl-N-(2-methylquinazolin-4-yl)benzene-1,4-diamine 0.396 g (1.5 mmol) in THF 10 mL and DMF 3 mL was added methyl hydrazine carboxylate 0.135 g (1.5 mmol), followed by addition of carbonyldiimidazole (CDI) 0.243 g (1.5 mmol) at 23° C. The reaction mixture was stirred at 23° C. for 4 h, heated under reflux for 0.5 h, and then stirred at 23° C. for another 16 h. After removal of THF, the crude product was purified with gradient column chromatography (EtOAc/hexanes, 0% to 100%) to give the titled compound in 75% yield, which was used without further purification. 1H NMR (CD3OD, 400 MHz): δ 7.98 (s, 1H), 7.64 (d, 1H, J=8.4 Hz), 7.59-7.54 (m, 1H), 7.52 (d, 2H, J=8.3 Hz), 7.13 (d, 2H, J=8.6 Hz), 7.05 (d, 1H, J=7.2 Hz), 7.03-6.98 (m, 1H), 3.74 (s, 3H), 3.70 (s, 1H), 2.99 (s, 3H), 2.86 (s, 3H). m/e: 381.19 (M+1), 379.03 (M−1).

Provenance & Evidence