Ammonium Chloride → N4-(4,4-difluorocyclohexyl)quinazoline-4,8-diamine

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To a solution of N-(4,4-difluorocyclohexyl)-8-nitroquinazolin-4-amine (90 mg, 0.292 mmol) in EtOH (2 mL) were added iron powder (163 mg, 2.92 mmol) and NH4Cl (127 mg, 2.33 mmol) and the reaction mixture was heated at reflux for 2 h. Then the reaction mixture was filtered through celite. The celite bed was washed with 10% MeOH in CHCl3. The filtrate was washed with a saturated aq. NaHCO3 solution and water. The organic layer was separated, dried, filtered and concentrated to afford 70 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.38 (s, 1H), 7.64 (d, J=7.2 Hz, 1H), 7.35 (d, J=7.8 Hz, 1H), 7.19-7.14 (t, J=7.8 Hz, 1H), 6.87 (d, J=7.8 Hz, 1H), 5.71 (s, 2H), 4.38 (m, 1H), 2.09-1.97 (m, 6H), 1.73-1.69 (m, 2H); MS (m/z): 279.12 (M+H)+.

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