4-(2-Fluoro-5-methoxycarbonyloxy-4-methylanilino)-6-methoxy-7-nitroquinazoline hydrochloride → 7-Amino4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)-6-methoxyquinazoline hydrochloride
Reaction equation
[ClH:1].[F:2][C:3]1[CH:24]=[C:23]([CH3:25])[C:22]([O:26][C:27]([O:29][CH3:30])=[O:28])=[CH:21][C:4]=1[NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([N+:18]([O-])=O)=[C:13]([O:16][CH3:17])[CH:14]=2)[N:9]=[CH:8][N:7]=1>[Pd].CO.C(O)C>[ClH:1].[NH2:18][C:12]1[CH:11]=[C:10]2[C:15]([C:6]([NH:5][C:4]3[CH:21]=[C:22]([O:26][C:27]([O:29][CH3:30])=[O:28])[C:23]([CH3:25])=[CH:24][C:3]=3[F:2])=[N:7][CH:8]=[N:9]2)=[CH:14][C:13]=1[O:16][CH3:17]Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
A mixture of 4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)-6-methoxy-7-nitroquinazoline hydrochloride (1.1 g, 25 mmol) and 10% palladium-on-charcoal catalyst (220 mg) in methanol (200 ml) and ethanol (10 ml) was stirred under hydrogen at 2.7 atmospheres for 7 hours. The catalyst was removed by filtration through diatomaceous earth, the solvent removed from the filtrate by evaporation and the solid residue washed with ether, collected by filtration and dried under vacuum to give 7-amino4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)-6-methoxyquinazoline hydrochloride (930 mg, 91%).
Workup
- customThe catalyst was removed by filtration through diatomaceous earth
- customthe solvent removed from the filtrate by evaporation
- washthe solid residue washed with ether
- filtrationcollected by filtration
- customdried under vacuum
Sources & evidence
- ORD record
- ord-9b3cd4a76e4c47dd8006335f5e48e243
- Source dataset
- uspto-grants-2001_02
- Patent number
- US06184225B2
Reaction notes
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