7-Benzyloxy-4-(4-chloro-2-fluorophenoxy)-6-methoxyquinazoline → 4-(4-Chloro-2-fluorophenoxy)-7-hydroxy-6-methoxyquinazoline

HRID 1384589Notes

Reaction equation

HRID 1384589 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][C:23]([Cl:26])=[CH:22][C:21]=3[F:27])=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:28][CH3:29])C1C=CC=CC=1>C(O)(C(F)(F)F)=O.C1(C)C=CC=CC=1>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([O:19][C:13]2[C:12]3[C:17](=[CH:18][C:9]([OH:8])=[C:10]([O:28][CH3:29])[CH:11]=3)[N:16]=[CH:15][N:14]=2)=[C:21]([F:27])[CH:22]=1

Participants

4

Reactant 1

HCID 218748257-Benzyloxy-4-(4-chloro-2-fluorophenoxy)-6-methoxyquinazoline

Product 1

HCID 1356162044-(4-Chloro-2-fluorophenoxy)-7-hydroxy-6-methoxyquinazolineYield 90.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 7-benzyloxy-4-(4-chloro-2-fluorophenoxy)-6-methoxyquinazoline (451 mg, 1.1 mmol) in TFA (4.5 ml) was heated at reflux for 3 hours. The mixture was diluted with toluene and the volatiles removed by evaporation. The residue was triturated with methylene chloride, collected by filtration, washed with ether and dried under vacuum to give 4-(4-chloro-2-fluorophenoxy)-7-hydroxy-6-methoxyquinazoline (320 mg, 90%). 1H NMR Spectrum: (DMSOd6) 4.0(s, 3H); 7.27(s, 1H); 7.43(dd, 1H); 7.56(t, 1H); 7.57(s, 1H); 7.72(dd, 1H); 8.5(s, 1H) MS-ESI: 321 [MH]+

Workup

  1. temperatureat reflux for 3 hours
  2. customthe volatiles removed by evaporation
  3. customThe residue was triturated with methylene chloride
  4. filtrationcollected by filtration
  5. washwashed with ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-edd41af82f044ab1a45d1931d2c3a6a1
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

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