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

HRID 1838527Notes

Reaction equation

HRID 1838527 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-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

  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-e30db74d72eb4da5bd1eaa7295640cd1
Source dataset
uspto-grants-2004_01
Patent number
US06673803B2

Reaction notes

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