反应详情

A stirred mixture of 3-[2-(3-nitrophenyl)-2-oxoethyl]-3H-quinazolin-4-one (2.00 g, 6.47 mmol), N,N-dimethyl-1,2-ethanediamine (2.28 g, 25.9 mmol), and p-toluenesulfonic acid (2.23 g, 12.9 mmol) in xylenes (150 mL) was refluxed for 48 h. After cooling to rt, water (20 mL) and sat. NaHCO3 (aq) (15 mL) were added. Layers were separated, and the aqueous phase was extracted with EtOAc (3×50 mL). The combined organic phases were dried over MgSO4, filtered, concentrated, and purified by silica gel chromatography (8% MeOH in CH2Cl2) to afford the desired product. 1H-NMR (CD3OD, 400 MHz): δ=2.15 (s, 6H), 2.54 (t, J=7.2 Hz, 2H), 4.22 (t, J=6.8 Hz, 2H), 7.15 (d, J=1.2 Hz, 1H), 7.74 (t, J=8.0 Hz, 1H), 7.89 (dt, J=2.4, 7.6 Hz, 1H), 7.90 (s, 1H), 8.24-8.26 (m, 1H), 8.30 (s, 1H). MS (ES+): m/z 261.24 [MH+]. HPLC: tR=0.49 and 0.71 min (ZQ2000, polar—5 min).

1. temperaturewas refluxed for 48 h
2. customLayers were separated
3. extractionthe aqueous phase was extracted with EtOAc (3×50 mL)
4. dry with materialThe combined organic phases were dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. custompurified by silica gel chromatography (8% MeOH in CH2Cl2)