4-(3-Acetoxy-4-methylanilino)-7-benzyloxy-6-methoxyquinazoline → 4-(3-Acetoxy-4-methylanilino)-7-hydroxy-6-methoxyquinazoline
Reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:29]=[CH:30][C:31]=1[CH3:32])[NH:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:21]CC3C=CC=CC=3)=[C:16]([O:19][CH3:20])[CH:17]=2)[N:12]=[CH:11][N:10]=1)(=[O:3])[CH3:2].[H][H]>[Pd].CO.CN(C=O)C.ClC(Cl)Cl>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:29]=[CH:30][C:31]=1[CH3:32])[NH:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([OH:21])=[C:16]([O:19][CH3:20])[CH:17]=2)[N:12]=[CH:11][N:10]=1)(=[O:3])[CH3:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Procedure
A mixture of 7-benzyloxy-4-chloro-6methoxyquinazoline (2.18 g, 7.25 mmol), 3-acetoxy-4-methylaniline (1.32 g, 8 mmol) and 2-propanol (50 ml) was stirred and heated to reflux for 1 hour. The mixture was cooled to ambient temperature. The precipitate was collected by filtration, washed with 2-propanol and ether to give 4-(3-acetoxy-4-methylanilino)-7-benzyloxy-6-methoxyquinazoline. A mixture of 4-(3-acetoxy-4-methylanilino)-7-benzyloxy-6-methoxyquinazoline (2.68 g, 5.75 mmol), 10% palladium-on-charcoal catalyst (0.27 g) in methanol (50 ml), DMF (12 ml) and trichloromethane (50 ml) was stirred at ambient temperature under 1.5 atmospheres of hydrogen for 30 minutes The catalyst was removed by filtration and the filtrate evaporated. The residual solid was triturated in ether, collected by filtration and dried under vacuum at 50° C. to give 4-(3-acetoxy-4-methylanilino)-7-hydroxy-6-methoxyquinazoline (2.1 g, 100%).
Workup
- customwas removed by filtration
- customthe filtrate evaporated
- customThe residual solid was triturated in ether
- filtrationcollected by filtration
- customdried under vacuum at 50° C.
Sources & evidence
- ORD record
- ord-6d39108c2468445fb0872599d4b70e96
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06673803B2
Reaction notes
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