Citric Acid → 7-Benzyloxy-3-methylpivaloyl-3,4-dihydroquinazolin-4-one

HRID 1596279Notes

Reaction equation

HRID 1596279 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=[O:19])[NH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[H][H].[C:24]([O:30]CCl)(=O)[C:25]([CH3:28])([CH3:27])[CH3:26].[C:33](O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=[O:19])[NH:14][C:15]([C:24](=[O:30])[C:25]([CH3:28])([CH3:27])[CH2:26][CH3:33])=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 311Citric AcidHCID 24758Sodium hydrideHCID 87885Chloromethyl pivalateHCID 1357631107-(Benzyloxy)-3,4-dihydroquinazolin-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 1361618157-Benzyloxy-3-methylpivaloyl-3,4-dihydroquinazolin-4-oneYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Benzyloxy-3,4-dihydroquinazolin-4-one (5.3 g, 21 mmol) was suspended in dry DMF (50 ml) and sodium hydride (1 g of a 60% suspension in mineral oil, 25 mmol) was added. After hydrogen evolution had ceased, the reaction was allowed to cool to ambient temperature and then chloromethyl pivalate (4.1 g, 27 mmol) was added dropwise over 10 minutes. The mixture was stirred for 30 minutes then poured into aqueous citric acid solution (pH5) (250 ml) and extracted with ether (3×300 ml). The combined extracts were washed with brine, dried (MgSO4) and the solvent removed by evaporation. The resulting solid was triturated with isohexane, collected by filtration and dried under vacuum to give 7-benzyloxy-3-methylpivaloyl-3,4-dihydroquinazolin-4-one (6.9 g, 90%).

Workup

  1. extractionextracted with ether (3×300 ml)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed by evaporation
  5. customThe resulting solid was triturated with isohexane
  6. filtrationcollected by filtration
  7. customdried under vacuum

Sources & evidence

ORD record
ord-ad6927ea41c34e35adc0f2c8c6234cfd
Source dataset
uspto-grants-2001_09
Patent number
US06291455B1

Reaction notes

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