Phosphorus oxychloride → 4-Chloro-5-(ethyloxy)-7-(methyloxy)quinazoline
Reaktionsgleichung
[CH2:1]([O:3][C:4]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[C:10]2[C:5]=1[C:6](=O)[N:7]=[CH:8][NH:9]2)[CH3:2].O=P(Cl)(Cl)[Cl:19]>CN(C=O)C>[Cl:19][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:14][CH3:15])=[CH:13][C:4]=2[O:3][CH2:1][CH3:2])[N:9]=[CH:8][N:7]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
A mixture of 5-(ethyloxy)-7-(methyloxy)-4(1H)-quinazolinone (285 mg, 1.29 mmol) in POCl3 (10 mL, 107 mmol) was treated with 1 drop of DMF and stirred at 100° C. for 1 hour before being concentrated. The residue was treated with saturated aqueous NaHCO3 and extracted with CH2Cl2. The organic extracts were dried (sodium sulfate), concentrated, and subjected to flash chromatography (1-3% MeOH—CH2Cl2) to give 4-chloro-5-(ethyloxy)-7-(methyloxy)quinazoline (260 mg, 84%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.84 (s, 1 H), 7.03 (d, J=2.51 Hz, 1 H), 6.84 (d, J=2.26 Hz, 1 H), 4.22 (q, J=6.86 Hz, 2 H), 3.96 (s, 3 H), 1.47 (t, J=6.90 Hz, 3 H). MS (m/z) 239.0 (M+H+).