267243-68-5

267243-64-1

267243-68-5

N-(3-chloro-4-fluorophenyl)-7-(3-morpholinopropoxy)-6-nitroquinazolin-4-amine (1.0 eq.) and NiCl2-6H2O (2.0 eq.) were used as raw materials, which were dissolved in a solvent mixture of dichloromethane/methanol (32 mL:8 mL). The reaction mixture was stirred at 0 °C for 5 min, followed by the addition of NaBH4 (4.0 eq.) in batches. After addition, the ice bath was removed and the reaction mixture was allowed to warm naturally to room temperature and stirring was continued for 30 minutes. Upon completion of the reaction, the solvent was removed by concentration under reduced pressure to give the crude product. The crude product was purified by column chromatography (eluent ratio 10:1 dichloromethane/methanol) to afford N-(3-chloro-4-fluorophenyl)-7-(3-morpholino-propoxy)quinazoline-4,6-diamine as a pale yellow solid in 50% yield.1H NMR (500 MHz, DMSO) δ 9.39 (s, 1H), 8.37 (s, 1H), 8.20 (d, J = 4.5 Hz, 1H), 7.81 (d, J = 8.5 Hz, 1H), 7.41-7.38 (m, 2H), 7.08 (s, 1H), 5.35 (s, 2H), 4.20 (t, J = 5.5 Hz, 2H), 3.59 (t, J = 4.5 Hz, 4H), 3.18 (d, J = 5.0 Hz, 2H), 2.40 (s, 4H), 2.01-1.96 (m, 2H).HRMS (ESI): m/z Calculated value (C21H23ClFN5O2 + H)+: 432.1603.Measured value: 432.1613.