Trifluoroacetic acid → 4-(4-Chloro-2-fluorophenoxy)-7-hydroxy-6-methoxyquinazoline

HRID 1357713Notes

Reaction equation

HRID 1357713 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.FC(F)(F)C(O)=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 2

HCID 6422Trifluoroacetic acidHCID 218748257-Benzyloxy-4-(4-chloro-2-fluorophenoxy)-6-methoxyquinazoline

Product 1

HCID 1356162044-(4-Chloro-2-fluorophenoxy)-7-hydroxy-6-methoxyquinazolineYield 105.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 7-benzyloxy-4-(4-chloro-2-fluorophenoxy)-6-methoxyquinazoline (23 g) and trifluoroacetic acid (150 ml) was stirred and heated to reflux for 3 hours. The reaction mixture was allowed to cool to ambient temperature. Toluene was added and the mixture was evaporated. The residue was triturated under diethyl ether and then under acetone. The precipitate was collected by filtration and dried to give 4-(4-chloro-2-fluorophenoxy)-7-hydroxy-6-methoxyquinazoline (19 g) which was used without further purification; NMR: (DMSOd6) 3.97 (s, 3H), 7.22 (s, 1H), 7.39 (d, 1H), 7.53 (m, 2H), 7.67 (m, 1H), 8.46 (s, 1H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. customthe mixture was evaporated
  4. customThe residue was triturated under diethyl ether
  5. filtrationThe precipitate was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-c33ba17b71814227a5607ee3a4d1cc39
Source dataset
uspto-grants-2003_07
Patent number
US06593333B1

Reaction notes

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