179552-75-1

179552-74-0

179552-75-1

General procedure for the synthesis of N4-(3-chloro-4-fluorophenyl)-7-methoxy-6-nitroquinazolin-4-amine from N-(3-chloro-4-fluorophenyl)-7-methoxyquinazolin-4,6-diamine: N-(3-chloro-4-fluorophenyl)-7-methoxy-6-nitroquinazolin-4-amine (10 g, 28.6 mmol) was dissolved in ethanol (200 mL) and THF (100 mL) in a solvent mixture. To this solution, water (50 mL) and saturated ammonium chloride solution (50 mL) were sequentially added at room temperature, followed by iron powder (6.5 g, 116 mmol). The reaction mixture was heated to 80 °C and the reaction was stirred at this temperature for 3 hours. After completion of the reaction, the mixture was filtered through diatomaceous earth and the filter cake was washed with ethanol. Water (100 mL) was added to the filtrate and a yellow-white solid precipitated. The solid was filtered and dried to afford the target compound N4-(3-chloro-4-fluorophenyl)-7-methoxyquinazoline-4,6-diamine (8 g, 88% yield) as a yellow solid.1H-NMR (400 MHz, DMSO-d6): δ 9.41 (s, 1H), 8.38 (s, 1H), 8.20-8.17 (m, 1H), 7.82- 7.80 (m, 1H), 7.41-7.37 (m, 2H), 5.36 (s, 2H), 3.97 (s, 3H).