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

HRID 1597219Notes

Reaction equation

HRID 1597219 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-19132787bad64a3fb6001b192c0e7d8c
Source dataset
uspto-grants-2001_09
Patent number
US06294532B1

Reaction notes

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