Water → HCID 71678052, compound

Participants

Reaction Steps

To a solution of 4-chloro-8-nitroquinazoline (Intermediate-7, step-2, 150 mg, 0.72 mmol) in CH3CN (3 mL) were added K2CO3 (300 mg, 2.15 mmol) and 4,4-dimethylcyclohexanamine hydrochloride (352 mg, 2.15 mmol) and the reaction mixture was heated at reflux for 3 h. Then water was added to the reaction mixture and it was extracted with EtOAc. The organic layer was washed with brine, separated, dried, filtered and concentrated. The residue was purified by column chromatography to afford 150 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.58-8.55 (d, J=8.4 Hz, 1H), 8.50 (s, 1H), 8.38-8.35 (d, J=7.2 Hz, 1H), 8.25-8.22 (d, J=7.8 Hz, 1H), 7.67-7.61 (t, J=7.8 Hz, 1H), 4.17 (m, 1H), 1.75-1.56 (m, 4H), 1.46-1.18 (m, 4H), 0.98 (s, 3H), 0.95 (s, 3H); MS [M+H]+: 301.20.

Provenance & Evidence