HCID 21699262, compound → 7-Hydroxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one

HRID 1386318Notes

Reaction equation

HRID 1386318 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=[O:27])[N:14]([CH2:19][O:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[CH:15]=[N:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>C(O)(C(F)(F)F)=O>[OH:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=[O:27])[N:14]([CH2:19][O:20][C:21](=[O:26])[C:22]([CH3:23])([CH3:24])[CH3:25])[CH:15]=[N:16]2)=[CH:11][CH:10]=1

Participants

3

Reactant 1

HCID 21699262HCID 21699262, compound

Product 1

HCID 216992947-Hydroxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-oneYield 90%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

7-benzyloxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (8.0 g, 22 mmol) was dissolved in TFA (40ml) and the mixture heated at reflux for 3 hours then allowed to cool to ambient temperature and stirred for 18 hours. The TFA was removed by evaporation and the residue resuspended in a mixture of ether and aqueous sodium hydrogen carbonate solution. The solid was collected by filtration, washed with water and ether and dried at 40° C. for 3 hours under high vacuum to give 7-hydroxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (5.42 g, 90%).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 3 hours
  3. customThe TFA was removed by evaporation
  4. additionthe residue resuspended in a mixture of ether and aqueous sodium hydrogen carbonate solution
  5. filtrationThe solid was collected by filtration
  6. washwashed with water and ether
  7. customdried at 40° C. for 3 hours under high vacuum

Sources & evidence

ORD record
ord-3185c67c3550445ab72c53bfbc6bf52f
Source dataset
uspto-grants-2001_07
Patent number
US06265411B1

Reaction notes

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