7-Benzyloxy-6-methoxy-4-phenoxyquinazoline → 7-Hydroxy-6-methoxy-4-phenoxyquinazoline

HRID 634691Notes

Reaction equation

HRID 634691 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:26][CH3:27])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:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:26][CH3:27]

Participants

3

Reactant 1

HCID 218748147-Benzyloxy-6-methoxy-4-phenoxyquinazoline

Product 1

HCID 1354961377-Hydroxy-6-methoxy-4-phenoxyquinazolineYield 89%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

7-Benzyloxy-6-methoxy-4-phenoxyquinazoline (160 mg, 0.44 mmol) in TFA (3 ml) was heated at reflux for 30 minutes. The solvent was removed by evaporation and the residue treated with aqueous sodium hydrogen carbonate solution. The precipitated product was collected by filtration, washed with water and dried to give 7-hydroxy-6-methoxy-4-phenoxyquinazoline (105 mg, 88%).

Workup

  1. temperatureat reflux for 30 minutes
  2. customThe solvent was removed by evaporation
  3. additionthe residue treated with aqueous sodium hydrogen carbonate solution
  4. filtrationThe precipitated product was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-ca42766ddb2a45ce9dca4a7cdb978da1
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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