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

HRID 1351191Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1351191
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:8][CH:9]=[N:10]2)=[CH:5][C:4]=1[OH:20].C([O-])([O-])=O.[K+].[K+].[CH2:27](Br)[CH:28]=[CH2:29]>CC(C)=O>[CH2:29]([O:20][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:3]=1[O:2][CH3:1])[N:10]=[CH:9][N:8]=[C:7]2[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:28]=[CH2:27]

Komponenten

5

Edukt 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 210984067-Methoxy-4-phenylamino-quinazolin-6-ol

Produkt 1

HCID 21098404(6-Allyloxy-7-methoxy-quinazolin-4-yl)-phenyl-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 7-methoxy-4-phenylamino-quinazolin-6-ol (0.56 g, 2.1 mmol) (from Example 15, Step B, supra) in acetone (50 mL) was added K2CO3 (1.45 g, 10 mmol), and allyl bromide (0.2 mL, 2.3 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 (1:4:0.04) as eluent to give the desired (6-allyloxy-7-methoxy-quinazolin-4-yl)-phenyl-amine as a yellow solid. (Yield 0.6 g, 93%).

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-9d038743e53d480b9ea7fe6976e1c08f
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07217717B2

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