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

HRID 453983Notes

Reaction equation

HRID 453983 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 96%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

7-Benzyloxy-6-methoxy-4-phenoxyquinazoline (36.95 g, 105.5 mmol) was suspended in TFA (420 ml) and heated at reflux for 3 hours. The reaction mixture was allowed to cool and evaporated under vacuum. The residue was stirred mechanically in water then basified with saturated aqueous sodium hydrogen carbonate solution and stirred overnight. The water was decanted and the solid suspended in acetone. After stirring the white solid was collected by filtration, washed with acetone and dried to give 7-hydroxy-6-methoxy-4-phenoxyquinazoline (26.61 g, 96%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. temperatureto cool
  4. customevaporated under vacuum
  5. stirringstirred overnight
  6. customThe water was decanted
  7. stirringAfter stirring the white solid
  8. filtrationwas collected by filtration
  9. washwashed with acetone
  10. customdried

Sources & evidence

ORD record
ord-3b2faee5f001413abb79fc6904f74e69
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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