Reaktion #473470

Reaktionsgleichung

4,7-dichloroquinazoline

MeONa

→

title compound

7-Chloro-4-methoxy-2-phenylquinazoline

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeequipped with a reflux condenser
2. 2
   Sonstigewas evacuated
3. 3
   workup.ADDITIONrefilled with Ar several times
4. 4
   Temperaturthe reaction mixture was heated
5. 5
   Temperaturto reflux under Ar for 5 h
6. 6
   Sonstigethen partitioned between DCM (80 mL) and H2O (10 mL)
7. 7
   ExtraktionThe aqueous layer was extracted with DCM (1×)
8. 8
   WaschenThe combined organics were washed (brine)
9. 9
   Trocknendried (Na2SO4)
10. 10
    Einengenconcentrated under reduced pressure

Vorschrift

A flask containing 4,7-dichloroquinazoline (250 mg, 0.91 mmol) equipped with a reflux condenser was evacuated and refilled with Ar several times. MeONa (2 mL, 25% wt in MeOH, 8.7 mmol) and anh. MeOH (20 mL) were added and the reaction mixture was heated to reflux under Ar for 5 h. The reaction was cooled to rt and stored at rt overnight then partitioned between DCM (80 mL) and H2O (10 mL). The aqueous layer was extracted with DCM (1×). The combined organics were washed (brine), dried (Na2SO4) and concentrated under reduced pressure to provide the title compound as an off-white solid; 1H NMR (400 MHz, CDCl3) δ 8.55-8.62 (m, 2H), 8.08 (d, J=9.2 Hz, 1H), 7.99 (d, J=2.0 Hz, 1H), 7.52-7.48 (m, 3H), 7.45 (dd, J=2.0 Hz, 8.8 Hz, 1H), 4.28 (s, 3H).

Quelle