Hydrochloric Acid → HCID 69358771, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of pyrrolidine (0.016 ml), 7-[(2R)-2,3-epoxypropoxy]-6-methoxy-4-(2,3-methylenedioxyanilino)quinazoline (0.03 g), chloroform (0.5 ml) and ethanol (0.5 ml) was stirred and heated to 40° C. for 7 hours. The mixture was evaporated and the residue was dissolved in methylene chloride (4 ml). A polystyrene isocyanate resin (prepared according to J. Amer. Chem. Soc., 1997, 119, 4882; loading: 1 mmol/g; 0.3 g) was added and the mixture was shaken at ambient temperature for 1.5 hours. The resin was removed by filtration and washed with methylene chloride. The filtrate was evaporated and the crude product so obtained was purified by column chromatography on silica using increasingly polar mixtures of methylene chloride and a saturated methanolic ammonia solution as eluent. The material so obtained was dissolved in a 9:1 mixture of methylene chloride and methanol (3 ml) and a 2.2M solution. of hydrogen chloride in diethyl ether (1 ml) was added. The precipitate was isolated and dried under vacuum. There was thus obtained the title compound (0.026 g); NMR Spectrum: (DMSOd6 and CF3CO2D) 1.85–2.15 (m, 4H), 3.06–3.25 (m, 2H), 3.31–3.47 (m, 2H), 3.6–3.74 (m, 2H), 4.04 (s, 3H), 4.8 (d,2H), 4.38–4.46 (m, 1H), 6.1 (s, 2H), 6.94–7.05 (m, 3H), 7.49 (s, 1H), 8.27 (s, 1H), 8.88 (s, 1H); Mass Spectrum: M+H+ 439.

Provenance & Evidence