Potassium Carbonate → 7-Benzyloxy-6-methoxy-4-(3-methylindol-5-yloxy)quinazoline

HRID 1791785

Reaktionsgleichung

[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](Cl)=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[OH:28][C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[NH:34][CH:33]=[C:32]2[CH3:38]>CC(N(C)C)=O>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:28][C:29]3[CH:30]=[C:31]4[C:35](=[CH:36][CH:37]=3)[NH:34][CH:33]=[C:32]4[CH3:38])=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 75 °C

Versuchsvorschrift

A mixture of 7-benzyloxy-4-chloro-6-methoxyquinazoline (7.859 g, 26.1 mmol), (prepared as described for the starting material in Example 1), potassium carbonate (18.03 g, 130 mmol) and 5-hydroxy-3-methylindole (5.00 g, 34.0 mmol), (Journal of Organic Chemistry 1993, 58, 3757), in DMA (600 ml) was stirred at 75° C. for 2 hours and allowed to cool to ambient temperature. The reaction mixture was filtered and the filtrate evaporated in vacuo. The crude solid was purified by silica column chromatography, eluting with 2.5% methanol/97.5% dichloromethane to give 7-benzyloxy-6-methoxy-4-(3-methylindol-5-yloxy)quinazoline (7.791 g, 73%).

Aufarbeitung

custom(prepared
temperatureto cool to ambient temperature
filtrationThe reaction mixture was filtered
customthe filtrate evaporated in vacuo
customThe crude solid was purified by silica column chromatography
washeluting with 2.5% methanol/97.5% dichloromethane

Quellen und Nachweise

ORD-Eintrag: ord-bac32f0e58ec4ba1a4f44945696ebe84
Quelldatensatz: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07074800B1

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