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

HRID 1596259Notes

Reaction equation

HRID 1596259 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]>[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

6

Reactant 1

HCID 224782894-(3-Acetoxy-4-methylanilino)-7-benzyloxy-6-methoxyquinazoline

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 4-(3-acetoxy-4-methylanilino)-7-benzyloxy-6-methoxyquinazoline (2.68 g, 5.75 mmol) and 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 hydrogen at 1.5 atmospheres pressure for 30 minutes. The catalyst was removed by filtration through diatomaceous earth and the solvent removed from filtrate by evaporation. The residue was triturated with 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 through diatomaceous earth
  2. customthe solvent removed from filtrate by evaporation
  3. customThe residue was triturated with ether
  4. filtrationcollected by filtration
  5. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-b1b280f1a049450aaa5df0e614425121
Source dataset
uspto-grants-2001_09
Patent number
US06291455B1

Reaction notes

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