Ammonia → 4-(5-Benzyloxy-2-fluoro4-methylanilino)-7-hydroxy-6-methoxyquinazoline

HRID 634678Notes

Reaction equation

HRID 634678 reaction equation
N.C([O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([NH:16][C:17]3[CH:22]=[C:21]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:20]([CH3:31])=[CH:19][C:18]=3[F:32])=[N:11][CH:12]=[N:13]2)=[CH:8][C:7]=1[O:33][CH3:34])(=O)C>CO>[CH2:24]([O:23][C:21]1[C:20]([CH3:31])=[CH:19][C:18]([F:32])=[C:17]([CH:22]=1)[NH:16][C:10]1[C:9]2[C:14](=[CH:15][C:6]([OH:5])=[C:7]([O:33][CH3:34])[CH:8]=2)[N:13]=[CH:12][N:11]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 212603127-Acetoxy4-(5-benzyloxy-2-fluoro-4-methylanilino)-6-methoxyquinazoline

Product 1

HCID 1355493824-(5-Benzyloxy-2-fluoro4-methylanilino)-7-hydroxy-6-methoxyquinazolineYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Concentrated aqueous ammonia (25 ml) was added to a solution of 7-acetoxy4-(5-benzyloxy-2-fluoro-4-methylanilino)-6-methoxyquinazoline (1.5 g, 3.4 mmol) in methanol (100 ml). The mixture was stirred at ambient temperature for 30 minutes, and most of the organic volatiles were then removed by evaporation. Further water was added and the precipitate was collected by filtration, washed with water and dried to give 4-(5-benzyloxy-2-fluoro-4-methylanilino)-7-hydroxy-6-methoxyquinazoline (1.2 g, 89%) which was used without further characterisation.

Workup

  1. custommost of the organic volatiles were then removed by evaporation
  2. additionFurther water was added
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-e96121c8a89c4848a5c6789ce011da8e
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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