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

HRID 454165Notes

Reaction equation

HRID 454165 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%).

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-375f0b3774a84719b9dbae849f1cf187
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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