Hydrochloric Acid → 4-(2-Fluoro-5-hydroxy4-methylanilino)-7-hydroxy-6-methoxyquinazoline

HRID 634714Notes

Reaction equation

HRID 634714 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:23]=[C:22]([CH3:24])[C:21]([O:25]C(OC)=O)=[CH:20][C:5]=1[NH:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([OH:19])=[C:14]([O:17][CH3:18])[CH:15]=2)[N:10]=[CH:9][N:8]=1.Cl>CO>[F:3][C:4]1[CH:23]=[C:22]([CH3:24])[C:21]([OH:25])=[CH:20][C:5]=1[NH:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([OH:19])=[C:14]([O:17][CH3:18])[CH:15]=2)[N:10]=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 1355493904-(2-Fluoro-5-methoxycarbonyloxy-4-methylanilino)-7-hydroxy-6-methoxyquinazoline

Product 1

HCID 1355493844-(2-Fluoro-5-hydroxy4-methylanilino)-7-hydroxy-6-methoxyquinazolineYield 45.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1M Aqueous sodium hydroxide solution (4 ml, 4 mmol) was added to a solution of 4-(2-fluoro-5-methoxycarbonyloxy4-methylanilino)-7-hydroxy-6-methoxyquinazoline (820 mg, 2.2 mmol) in methanol (20 ml) and the mixture stirred for 1 hour at ambient temperature. Concentrated hydrochloric acid (0.8 ml) was added, the volatiles removed by evaporation and the residue purified by column chromatography eluting with methylene chloride/methanol (60/40) to give 4-(2-fluoro-5-hydroxy4-methylanilino)-7-hydroxy-6-methoxyquinazoline (313 mg, 45%).

Workup

  1. customthe volatiles removed by evaporation
  2. customthe residue purified by column chromatography
  3. washeluting with methylene chloride/methanol (60/40)

Sources & evidence

ORD record
ord-21be697f4d1642c9870b42839caafa10
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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