Cesium carbonate → 3-(6-(Benzyloxy)-7-methoxyquinazolin-4-yloxy)aniline
Reaktionsgleichung
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]=[CH:14][N:13]=[C:12]2Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:22][C:23]1[CH:24]=[C:25]([OH:29])[CH:26]=[CH:27][CH:28]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]=[CH:14][N:13]=[C:12]2[O:29][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][CH:26]=1)[NH2:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 75 °C
Versuchsvorschrift
To a solution of 6-(benzyloxy)-4-chloro-7-methoxyquinazoline (3.3 g, 0.01097 mol) and 3-aminophenol (1.2 g, 0.01097 mol) in THF (70 mL), Cs2CO3 (5.36 g, 0.0164 mol) was added at room temperature. The reaction mixture was stirred at 75° C. for 25 hr. The mixture was filtered and the solid was washed with ethyl acetate (100 mL). The organic phase was washed with water, brine and dried over MgSO4. The solvent was evaporated under vacuum and the solid was triturated with ethyl ether (20 mL). The solid was filtered and washed with ethyl ether to afford 3-(6-(benzyloxy)-7-methoxyquinazolin-4-yloxy)aniline (3.72 g, 90% yield). 1HNMR (DMSO-d6): δ 8.55 (s, 1H), 7.66 (s, 1H,), 7.46 (m, 8H), 7.08 (t, 1H), 6.49 (d, 1H), 6.40 (m, 2H), 5.30 (s, 2H), 4.02 (s, 3H). LC-MS (ESI) m/z 508 (M+H)+.
Aufarbeitung
- filtrationThe mixture was filtered
- washthe solid was washed with ethyl acetate (100 mL)
- washThe organic phase was washed with water, brine
- dry with materialdried over MgSO4
- customThe solvent was evaporated under vacuum
- customthe solid was triturated with ethyl ether (20 mL)
- filtrationThe solid was filtered
- washwashed with ethyl ether
Quellen und Nachweise
- ORD-Eintrag
- ord-fa9a52df1e4342068b5cb0d81d1b6abe
- Quelldatensatz
- uspto-grants-2016_04
- Patentnummer
- US09320739B2
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