4,7-Dichloroquinazoline → HCID 57680999, Verbindung

HRID 244216Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 244216
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.[CH3:13][O:14][Na]>CO>[Cl:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([O:14][CH3:13])=[N:3][C:4]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)=[N:5]2)=[CH:10][CH:9]=1

Komponenten

4

Edukt 2

HCID 2418814,7-DichloroquinazolineHCID 178418582HCID 178418582, Verbindung

Produkt 1

HCID 57680999HCID 57680999, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A flask containing 4,7-dichlorquinazoline (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).

Aufarbeitung

  1. customequipped with a reflux condenser
  2. customwas evacuated
  3. additionrefilled with Ar several times
  4. temperaturethe reaction mixture was heated
  5. temperatureto reflux under Ar for 5 h
  6. customthen partitioned between DCM (80 mL) and H2O (10 mL)
  7. extractionThe aqueous layer was extracted with DCM (1×)
  8. washThe combined organics were washed (brine)
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-88036a6f56b14483833f9de99686b96f
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653268B2

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