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

HRID 1864356Notes

Reaction equation

[CH3:1][NH:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[C:8](=[O:16])[NH:9][CH:10]=[N:11]2.[C:17](OC(=O)C)(=[O:19])[CH3:18]>N1C=CC=CC=1>[CH3:1][N:2]([CH2:3][CH2:4][O:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[C:8](=[O:16])[NH:9][CH:10]=[N:11]2)[C:17](=[O:19])[CH3:18]

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

temperaturethe solution was warmed to ambient temperature
concentrationThe mixture was concentrated in vacuo
customthe residue purified by chromatography
washeluting with 4% to 7% (10:1 methanol/conc. NH3(aq)) in DCM
customEvaporation of the appropriate fractions

Sources & evidence

ORD record: ord-ff6df890afe44aedb3209fc0af8e7121
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625908B2

Reaction notes

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