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

HRID 453993Notes

Reaction equation

HRID 453993 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.C1(C)C=CC=CC=1>C(O)(C(F)(F)F)=O>[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 1140TolueneHCID 218748257-Benzyloxy-4-(4-chloro-2-fluorophenoxy)-6-methoxyquinazoline

Product 1

HCID 1356162044-(4-Chloro-2-fluorophenoxy)-7-hydroxy-6-methoxyquinazolineYield 1,999.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

7-Benzyloxy-4-(4-chloro-2-fluorophenoxy)-6-methoxyquinazoline (1.4 g, 3.4 mmol) was suspended in TFA (15 ml) and heated at reflux for 3 hours. The reaction mixture was allowed to cool, toluene was added and the volatiles were removed by evaporation under vacuum. The residue was triturated with ether and then acetone. The precipitate was collected by filtration and dried to give 4-(4-chloro-2-fluorophenoxy)-7-hydroxy-6-methoxyquinazoline (21.8 g). This was used without further purification in the next step.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. temperatureto cool
  4. customthe volatiles were removed by evaporation under vacuum
  5. customThe residue was triturated with ether
  6. filtrationThe precipitate was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-724911cf6bb14d178ff9b3f47811e26f
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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