Tetrahydrofuran → HCID 10437672, compound

Participants

Reaction Conditions

Reaction Steps

A solution of sodium bis(trimethylsilyl)amide (1.5 ml) in tetrahydrofuran (1.0M, 1.5 mmol) was added over 5 min. to a stirred mixture of 5-chloro-7-(3-methoxybut-1-yn-1-yl)-1,3-benzodioxol-4-yl-amine (0.190 g) and 4-chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline (0.230 g) in DMF (6.5 ml) cooled to 0° C. under a nitrogen atmosphere; the resultant mixture was stirred for 1 hr at ambient temperature. The reaction mixture was diluted with saturated aqueous ammonium chloride (70 ml) and extracted with ethyl acetate (3×25 ml). The organic extracts were washed with brine (25 ml), dried over sodium sulphate and then evaporated. The residue was purified by column chromatography on silica using increasingly polar mixtures of methanol in dichloromethane as eluent. There was thus obtained the title compound as a racemate and in the form of a solid (0.314 g). NMR Spectrum: (DMSOd6) 1.42 (d, 3H), 1.95 (m, 2H), 2.37 (m, 4H), 2.45 (t, 2H), 3.35 (s, 3H), 3.57 (m, 4H), 3.92 (s, 3H), 4.18 (t, 2H), 4.39 (q, 1H), 6.15 (s, 2H), 7.13 (s, 1H), 7.18 (s, 1H), 7.82 (s, 1H), 8.32 (s, 1H), 9.50 (s, 1H); Mass Spectrum: M+H+ 555 and 557.

Provenance & Evidence