Acetic Anhydride → N-methyl-N-{2-[(4-oxo-3,4-dihydroquinazolin-5-yl)oxy]ethyl}acetamide

Participants

Reaction Conditions

Reaction Steps

5-[2-(Methylamino)ethoxy]quinazolin-4(3H)-one (823 mg, 3.76 mmol) was dissolved in pyridine (25 ml), and the solution cooled to 0° C. Acetic anhydride (1.20 ml, 12.70 mmol) was added drop wise; the solution was warmed to ambient temperature and stirred for 90 minutes. The mixture was concentrated in vacuo, and the residue purified by chromatography, eluting with 4% to 7% (10:1 methanol/conc. NH3(aq)) in DCM. Evaporation of the appropriate fractions gave N-methyl-N-{2-[(4-oxo-3,4-dihydroquinazolin-5-yl)oxy]ethyl}acetamide as a white foam (970 mg, 99%); NMR Spectrum (DMSO-d6, 400 MHz, 373K) 2.05 (bs, 3H), 2.92 (s, 3H), 3.71 (bt, 2H), 4.20 (bt, 2H), 7.01 (d, 1H), 7.19 (d, 1H), 7.63 (dd, 1H), 7.89 (s, 1H); Mass spectrum M+NH4+284.0 (ES−) M−H+ 260.0.

Provenance & Evidence