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

HRID 1791516Notes

Reaction equation

HRID 1791516 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-36e35b2dcbe54393ad2cd3b23febd9d7
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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