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

HRID 1384530Notes

Reaction equation

HRID 1384530 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%). 1H NMR Spectrum: (DMSOd6) 4.00(s, 3H); 7.20(s, 1H); 7.25-7.35(m, 3H); 7.4-7.55(m, 2H); 7.58(s, 1H); 10.73(s, 1H) MS-ESI: 269 [MH]+

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-fb6eb260f83b4e3da7287ee993d35058
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

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