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

HRID 2227911Notes

Reaction equation

HRID 2227911 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](Cl)=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]([O:25][C:26]1[CH:27]=[C:28]([CH:30]=[CH:31][C:32]=1[CH3:33])[NH2:29])(=[O:24])[CH3:23]>CC(O)C>[C:22]([O:25][C:26]1[CH:27]=[C:28]([CH:30]=[CH:31][C:32]=1[CH3:33])[NH:29][C:13]1[C:12]2[C:17](=[CH:18][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:10]([O:20][CH3:21])[CH:11]=2)[N:16]=[CH:15][N:14]=1)(=[O:24])[CH3:23]

Participants

4

Reactant 2

HCID 106619987-(Benzyloxy)-4-chloro-6-methoxyquinazolineHCID 224783113-Acetoxy-4-methylaniline

Product 1

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

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 7-benzyloxy-4-chloro-6-methoxyquinazoline (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

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with 2-propanol and ether

Sources & evidence

ORD record
ord-75c81a2b9ca54624890a5cdaf11b8db6
Source dataset
uspto-grants-2002_07
Patent number
US06414148B1

Reaction notes

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