[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH:11]=O)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:27][O:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[N:35]=[CH:34][N:33]=[C:32]2[O:39][CH2:40][CH:41]1[CH2:46][CH2:45][CH:44]([NH2:47])[CH2:43][CH2:42]1>ClC(Cl)C>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][NH:47][CH:44]3[CH2:45][CH2:46][CH:41]([CH2:40][O:39][C:32]4[C:31]5[C:36](=[CH:37][CH:38]=[C:29]([O:28][CH3:27])[CH:30]=5)[N:35]=[CH:34][N:33]=4)[CH2:42][CH2:43]3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]12,3-Dihydro-benzo[1,4]dioxin-6-carbaldehyde (0.045 g, 0.27 mmol) and then sodium triacetoxyborohydride (0.08 g, 0.377 mmol) were added to a solution of 4-(6-methoxyquinazolin-4-yloxymethyl)-cyclohexylamine (0.07 g, 0.25 mmol) in dichloroethane (1 ml). The reaction mixture was stirred for 2 hours and then filtered over Hydromatrix (wetted with NaHCO3 solution, 2 ml) and subsequently washed with dichloromethane. The filtrate was concentrated to dryness by rotary evaporation. The residue was purified by column chromatography on silica gel (dichloromethane/MeOH 9/1 and then dichloromethane/MeOH 6/1).
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