Potassium Carbonate → 7-Benzyloxy-4-(2,3-dimethylindol-5-yloxy)-6-methoxyquinazoline

HRID 454157Notes

Reaction equation

[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+].[CH3:28][C:29]1[NH:30][C:31]2[C:36]([C:37]=1[CH3:38])=[CH:35][C:34]([OH:39])=[CH:33][CH:32]=2>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:39][C:34]3[CH:35]=[C:36]4[C:31](=[CH:32][CH:33]=3)[NH:30][C:29]([CH3:28])=[C:37]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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 7-benzyloxy-4-chloro-6-methoxyquinazoline (1.5 g, 4.99 mmol), (prepared as described for the starting material in Example 1), potassium carbonate (2.07 g, 15 mmol) and 2,3-dimethyl-5-hydroxyindole (1.21 g, 7.5 mmol), (Arch. Pharm. 1972, 305, 159), in DMF (75 ml) was stirred at 100° C. for 2 hours and allowed to cool to ambient temperature. The reaction mixture was filtered and the filtrate evaporated. The solid residue was purified by silica column chromatography, eluting with 2.5% methanol in dichoromethane to give 7-benzyloxy-4-(2,3-dimethylindol-5-yloxy)-6-methoxyquinazoline (976 mg, 46%).

Workup

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

Sources & evidence

ORD record: ord-12b150cc5e25498fae6c5565cf294aaa
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492560B2

Reaction notes

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