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

HRID 279546Notes

Reaction equation

HRID 279546 reaction equation
Cl.C([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=3[F:28])=[N:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:29][CH3:30])C1C=CC=CC=1>C(O)(C(F)(F)F)=O>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([NH:20][C:14]2[C:13]3[C:18](=[CH:19][C:10]([OH:9])=[C:11]([O:29][CH3:30])[CH:12]=3)[N:17]=[CH:16][N:15]=2)=[C:22]([F:28])[CH:23]=1

Participants

3

Reactant 1

HCID 224782657-Benzyloxy-4-(4-chloro-2-fluorophenylamino)-6-methoxyquinazoline hydrochloride

Product 1

HCID 1355137204-(4-Chloro-2-fluorophenylamino)-7-hydroxy-6-methoxyquinazolineYield 72%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 7-benzyloxy-4-(4-chloro-2-fluoroanilino)-6-methoxyquinazoline hydrochloride (892 mg, 2 mmol) in TFA (10 ml) was heated at reflux for 50 minutes. The mixture was allowed to cool and then poured on to ice. The precipitate was collected by filtration, dissolved in methanol (10 ml) and basified to pH11 with aqueous ammonia. The mixture was concentrated by evaporation, the resulting solid product was collected by filtration, washed with water then ether and dried under vacuum to give 4-(4-chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (460 mg, 72%) as a yellow solid.

Workup

  1. temperatureat reflux for 50 minutes
  2. temperatureto cool
  3. additionpoured on to ice
  4. filtrationThe precipitate was collected by filtration
  5. dissolutiondissolved in methanol (10 ml)
  6. concentrationThe mixture was concentrated by evaporation
  7. filtrationthe resulting solid product was collected by filtration
  8. washwashed with water
  9. dry with materialether and dried under vacuum

Sources & evidence

ORD record
ord-4c7883d045824795a9bf66d1e48e93f7
Source dataset
uspto-grants-2002_03
Patent number
US06362336B1

Reaction notes

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