Benzylamine → Benzyl-[4-(6-methoxy-quinazolin-4-yloxymethyl)-cyclohexyl]-amine

反応式

[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([BH3-])#N.[Na+].[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][N:19]=[C:18]2[O:25][CH2:26][CH:27]1[CH2:32][CH2:31][C:30](=O)[CH2:29][CH2:28]1>CO>[CH2:1]([NH:8][CH:30]1[CH2:29][CH2:28][CH:27]([CH2:26][O:25][C:18]2[C:17]3[C:22](=[CH:23][CH:24]=[C:15]([O:14][CH3:13])[CH:16]=3)[N:21]=[CH:20][N:19]=2)[CH2:32][CH2:31]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

実験手順

Benzylamine (1.08 ml, 10 mmol) and sodium cyanoborohydride (2.2 g, 11 mmol) were added to a solution of 4-(6-methoxy-quinazolin-4-yloxymethyl)-cyclohexanone (2.87 g, 10 mmol) in methanol (50 ml). The mixture was stirred overnight at room temperature. The reaction mixture was concentrated and the residue was dissolved in saturated potassium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate (2×50 ml), and the combined organic phases were dried over magnesium sulphate and concentrated. The residue was purified by column chromatography on silica gel (EtOAc and then EtOAc/MeOH 9/1).