4-(3-Acetoxy-4-methylanilino)-7-benzyloxy-6-methoxyquinazoline → 4-(3-Acetoxy-4-methylanilino)-7-hydroxy-6-methoxyquinazoline

HRID 2182524Notes

Reaction equation

HRID 2182524 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

7

Reactant 2

HCID 224782894-(3-Acetoxy-4-methylanilino)-7-benzyloxy-6-methoxyquinazolineHCID 178418361HCID 178418361, compound

Product 1

HCID 1354508044-(3-Acetoxy-4-methylanilino)-7-hydroxy-6-methoxyquinazolineYield 107.6%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-benzyloxy-4-chloro-6-methoxyquinazoline (20.8 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-4methylanilino)-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

  1. customThe catalyst was removed by filtration
  2. customthe filtrate evaporated
  3. customThe residual solid was triturated in ether
  4. filtrationcollected by filtration
  5. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-3a7092eac16e4252b34701e4a654ffe2
Source dataset
uspto-grants-2005_05
Patent number
US06897210B2

Reaction notes

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