7-Benzyloxy-4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)-6-methoxyquinazoline hydrochloride → 4-(2-Fluoro-5-methoxycarbonyloxy-4-methylanilino)-7-hydroxy-6-methoxyquinazoline hydrochloride

HRID 1420907Notes

Reaction equation

HRID 1420907 reaction equation
[ClH:1].C([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:20][C:21]3[CH:26]=[C:25]([O:27][C:28]([O:30][CH3:31])=[O:29])[C:24]([CH3:32])=[CH:23][C:22]=3[F:33])=[N:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:34][CH3:35])C1C=CC=CC=1>CN(C=O)C.CO.ClC(Cl)Cl.[Pd]>[ClH:1].[F:33][C:22]1[CH:23]=[C:24]([CH3:32])[C:25]([O:27][C:28]([O:30][CH3:31])=[O:29])=[CH:26][C:21]=1[NH:20][C:14]1[C:13]2[C:18](=[CH:19][C:10]([OH:9])=[C:11]([O:34][CH3:35])[CH:12]=2)[N:17]=[CH:16][N:15]=1

Participants

6

Reactant 1

HCID 226249307-Benzyloxy-4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)-6-methoxyquinazoline hydrochloride

Product 1

HCID 1356711794-(2-Fluoro-5-methoxycarbonyloxy-4-methylanilino)-7-hydroxy-6-methoxyquinazoline hydrochlorideYield 98%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 7-benzyloxy4-(2-fluoro-5-methoxycarbonyloxy4-methylanilino)-6-methoxyquinazoline hydrochloride (700 mg, 1.45mmol) in DMF (10 ml), methanol (10 ml) and trichloromethane (10 ml) containing 10% palladium-on-charcoal (100 mg) was stirred under an atmosphere of hydrogen for 1 hour. After filtration and evaporation of the solvent, the residue was triturated with ether, filtered and dried under vacuum to give 4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)-7-hydroxy-6-methoxyquinazoline hydrochloride (570 mg, 98%).

Workup

  1. filtrationAfter filtration and evaporation of the solvent
  2. customthe residue was triturated with ether
  3. filtrationfiltered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-3a084dddaf3941bc8b3aaa99e5d19bd7
Source dataset
uspto-grants-2000_06
Patent number
US06071921

Reaction notes

Loading…