Sodium hydride → 3-(2,6-dimethoxybenzyl)-6-hydroxy-3H-quinazolin-4-one

HRID 1603544Notes

Reaction equation

HRID 1603544 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][NH:8][C:7]2=[O:14].[CH3:15][O:16][C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[C:18]=1[CH2:19]Br>CN(C)C=O>[CH3:26][O:25][C:21]1[CH:22]=[CH:23][CH:24]=[C:17]([O:16][CH3:15])[C:18]=1[CH2:19][N:8]1[C:7](=[O:14])[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([OH:3])[CH:5]=2)[N:10]=[CH:9]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 155569582-(Bromomethyl)-1,3-dimethoxybenzeneHCID 1354895773,4-Dihydro-6-hydroxy-4-oxoquinazoline

Product 1

HCID 196057683-(2,6-dimethoxybenzyl)-6-hydroxy-3H-quinazolin-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

76 mg of sodium hydride (80% in mineral oil) are added to a suspension of 400 mg of 6-hydroxy-3H-quinazolin-4-one in 20 ml of dry dimethylformamide. After stirring for 30 minutes at room temperature, 560 mg of 2,6-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. Silica gel chromatography yields a minor amount of the N,O-bis-alkylated product followed by the pure title compound as colourless crystals. mp: 243-245°.

Workup

  1. stirringstirring
  2. waitis continued overnight
  3. distillationThe solvent is distilled off in vacuo
  4. customthe residue partitioned between aqueous pH7-buffer solution and ethyl acetate
  5. customThe organic phase is separated
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customSilica gel chromatography yields a minor amount of the N,O-bis-alkylated product

Sources & evidence

ORD record
ord-986f5b48d98b426ea1185b247b3c2d8d
Source dataset
uspto-grants-1999_11
Patent number
US05990116

Reaction notes

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