Ammonium Hydroxide → 4-((4-Bromo-2-fluorophenyl)amino)-7-methoxyquinazolin-6-ol

HRID 1351215Notes

Reaction equation

HRID 1351215 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[CH:10][N:9]=[C:8]2[NH:17][C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][C:19]=1[F:25])(=O)C.[NH4+].[OH-]>CO>[Br:24][C:21]1[CH:22]=[CH:23][C:18]([NH:17][C:8]2[C:7]3[C:12](=[CH:13][C:14]([O:15][CH3:16])=[C:5]([OH:4])[CH:6]=3)[N:11]=[CH:10][N:9]=2)=[C:19]([F:25])[CH:20]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 210983974-((4-Bromo-2-fluorophenyl)amino)-7-methoxyquinazolin-6-yl acetate

Product 1

HCID 210983904-((4-Bromo-2-fluorophenyl)amino)-7-methoxyquinazolin-6-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-acetoxy-4-(4-bromo-2-fluoro-phenylamino)-7-methoxy-quinazoline (1.36 g, 3.34 mmol) (from Example 19, Step A, supra) in MeOH (30 mL) was added an aqueous solution of NH4OH (29%, 0.68 mL, 10 mmol). The reaction mixture was stirred at room temperature for 18 hours, then heated at 100° C. for 1.5 hours. The mixture was then cooled to room temperature and filtered. The precipitate was collected and dried in vacuo to give the desired 4-(4-bromo-2-fluoro-phenylamino)-7-methoxy-quinazolin-6-ol as a gray solid. (Yield 0.93 g, 77%).

Workup

  1. temperatureheated at 100° C. for 1.5 hours
  2. temperatureThe mixture was then cooled to room temperature
  3. filtrationfiltered
  4. customThe precipitate was collected
  5. customdried in vacuo

Sources & evidence

ORD record
ord-0565a86a420d4024bff72ce310630ba4
Source dataset
uspto-grants-2007_05
Patent number
US07217717B2

Reaction notes

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