Stannous chloride dihydrate → [2-Amino-4-(benzyloxy)-5-methoxyphenyl][4-(4-quinazolinyl)piperazino]methanone

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Reaction Steps

[4-(Benzyloxy)-5-methoxy-2-nitrophenyl][4-(4-quinazolinyl)piperazino]methanone (600 mg, 1.2 mmol) was dissolved in methanol (10 mL), SnCl2.2H2O (810 mg, 3.6 mmol) was added and refluxed until the TLC indicated the completion of the reaction. The methanol was evaporated by vacuum and the aqueous layer was then adjusted to pH 8 with 10% NaHCO3 solution and extracted with ethyl acetate (2×30 mL). The combined organic phase was dried over Na2SO4 and evaporated under vacuum to afford the crude (450 mg, 95% yield). This was further purified by column chromatography using ethyl acetate:hexane (6:4) as a solvent system to obtain the pure product (8d) (672 mg, 80% yield). 1H NMR (CDCl3) δ 3.20-3.30 (m, 4H), 3.65-3.75 (m, 4H), 3.95 (s, 3H), 5.20 (s, 2H), 6.20 (s, broad NH2), 6.45-6.55, (t, 1H) 6.70 (s, 1H), 7.30-7.50 (m, 5H), 7.55-7.65 (t, 1H), 7.65 (s, 1H), 7.70-7.90, (m, 2H), 7.85-7.95, (m, 2H); FABMS: 470 (M+H)+.

Provenance & Evidence