Sodium bis(trimethylsilyl)amide → N-{5-chloro-7-[3-(2methoxyethoxy)prop-1-yn-1-yl]-1,3-benzodioxol-4-yl}-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazolin-4-amine

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Reaction Steps

This was prepared using the method described in example 4 using 4-chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline (200 mg, 0.59 mmol), 5-chloro-7-[3-(2-methoxyethoxy)prop-1-yn-1-yl]-1,3-benzodioxol-4-amine (185 mg, 0.65 mmol) and a solution of sodium bis(trimethylsilyl)amide (1.0M in THF, 1.24 ml) in DMF (3 ml). The crude product was purified by column chromatography on silica using increasing concentrations of methanol in dichloromethane as eluent. There was thus obtained the title compound (268 mg, 77%) as a pale yellow solid; NMR Spectrum: (DMSOd6) 1.99 (quintet, 2H), 2.40 (m, 4H), 2.49 (t, 2H), 3.30 (s,3H), 3.52 (m, 2H), 3.59 (m, 4H), 3.65 (m, 2H), 3.93 (s, 3H), 4.20 (t, 2H), 4.44 (s, 2H), 6.16 (s, 2H), 7.16 (s, 1H), 7.19 (s, 1H), 7.82 (s, 1H), 8.32 (s, 1H), 9.5 (s, 1H); Mass Spectrum: M+H+ 585/587.

Provenance & Evidence