Allyl bromide → (6-Allyloxy-7-methoxy-quinazolin-4-yl)-(3-bromo-phenyl)-amine

HRID 1351204Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1351204
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:20][CH3:21])=[C:16]([OH:19])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[CH2:28](Br)[CH:29]=[CH2:30]>CC(C)=O>[CH2:30]([O:19][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][C:15]=1[O:20][CH3:21])[N:12]=[CH:11][N:10]=[C:9]2[NH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[CH:29]=[CH2:28]

Komponenten

5

Edukt 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 103829564-(3-Bromoanilino)-6-hydroxy-7-methoxyquinazoline

Produkt 1

HCID 21098400(6-Allyloxy-7-methoxy-quinazolin-4-yl)-(3-bromo-phenyl)-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 4-(3-bromo-phenylamino)-7-methoxy-quinazolin-6-ol (1.24 g, 3.58 mmol) (from Example 17, Step B, supra) in acetone (250 mL) was added K2CO3 (0.99 g, 7.16 mmol), and allyl bromide (1.55 mL, 17.9 mmol) (Aldrich). The reaction mixture was heated with stirring at 90° C. for 4 hours. The mixture was cooled to room temperature, filtered and the filtrate was concentrated. The residue was purified by chromatography using EtOAc/CH2Cl2/Et3N (2:3:0.02) as eluent to give the desired (6-allyloxy-7-methoxy-quinazolin-4-yl)-(3-bromo-phenyl)-amine as a yellow oil. (Yield 0.55 g, 40%).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1dc1d6917a6c416185049de7521a85b6
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07217717B2

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