Dimethylformamide → 3-(2,6-Dimethoxybenzyl)-6-(2,5-dimethoxybenzyloxy)-3H-quinazolin-one
Reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[C:6]=1[CH2:7][N:8]1[C:17](=O)[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:19])[CH:15]=2)[N:10]=[CH:9]1.[CH3:26][O:27][C:28]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][C:29]=1[CH2:30]Br.CN(C)C=[O:41]>>[CH3:3][O:4][C:5]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[C:6]=1[CH2:7][N:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[CH:13][C:14]([O:19][CH2:30][C:29]3[CH:32]=[C:33]([O:36][CH3:37])[CH:34]=[CH:35][C:28]=3[O:27][CH3:26])=[CH:15]2)=[N:10][C:9]1=[O:41]Participants
5
Procedure
12 mg of sodium hydride (80% in mineral oil) are added to a solution of 115 mg of 3-(2,6-dimethoxybenzyl)-6-hydroxy-3H-quinazolin-4-one in 10 ml of dry dimethylformamide. After stirring for 30 minutes at room temperature, 85 mg of 2,5-dimethoxybenzylbromide are added, and stirring is continued overnight. The solvent is distilled off in vacuo, and the residue partitioned between aqueous pH7-buffer solution and ethyl acetate. The organic phase is separated, dried over magnesium sulfate and evaporated in vacuo. The pure title compound is obtained after silica gel chromatography (toluene/ethyl acetate=2/1) as colourless crystals. mp: 148-150°.
Workup
- stirringstirring
- waitis continued overnight
- distillationThe solvent is distilled off in vacuo
- customthe residue partitioned between aqueous pH7-buffer solution and ethyl acetate
- customThe organic phase is separated
- dry with materialdried over magnesium sulfate
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-98376f61979d4cf8807b633319237d0f
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05990116
Reaction notes
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