Triphenylphosphine → 1-{3-[(4-Chloro-6-methoxyquinazolin-7-yl)oxy]propyl}-4-methylpiperazin-2-one

Participants

Reaction Steps

Di-tert-butylazodicarboxylate (393 mg, 1.71 mmol) was added portionwise, at room temperature, to a stirred suspension of 4-chloro-6-methoxyquinazolin-7-ol, (300 mg, 1.42 mmol), 1-(3-hydroxypropyl)-4-methylpiperazin-2-one (270 mg, 1.57 mmol) and triphenylphosphine (522 mg, 1.99 mmol) in dichloromethane (10 ml). The reaction was stirred 1 hr before adding further di-tert-butylazodicarboxylate (393 mg) and triphenylphosphine (522 mg) and stirring for a further 1 hr. The resulting reaction solution was purified by column chromatography on silica using increasing concentrations of methanol in dichloromethane as eluent to give 1-{3-[(4-chloro-6-methoxyquinazolin-7-yl)oxy]propyl}-4-methylpiperazin-2-one (260 mg, 50%) as a pale yellow solid; NMR Spectrum:(DMSOd6) 2.06 (quintet, 2H), 2.20 (s, 3H), 2.60 (t, 2H), 2.91 (s, 2H), 3.33 (t, 2H), 3.48 (t, 2H), 4.00 (s, 3H), 4.22 (t, 2H), 7.40 (s, 1H), 7.41 (s, 1H), 8.87 (s, 1H); Mass Spectrum: M+H+ 365/367.

Provenance & Evidence