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

HRID 1596258Notes

Reaction equation

HRID 1596258 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]>C(O)(C)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-benzyloxy4-chloro-6-methoxyquinazoline (2.18 g, 7.25 mmol), (prepared as described for the starting material in Example 4), 3-acetoxy-4-methylaniline (1.32 g, 8 mmol) and isopropanol (50 ml) was stirred and heated at reflux for 1 hour. The mixture was cooled to ambient temperature. The precipitate was collected by filtration, washed with isopropanol and ether to give 4-(3-acetoxy-4-methylanilino)-7-benzyloxy-6-methoxyquinazoline.

Workup

  1. custom(prepared
  2. temperatureheated
  3. temperatureat reflux for 1 hour
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with isopropanol and ether

Sources & evidence

ORD record
ord-2e765a88cad344cfbe24f03caaa68585
Source dataset
uspto-grants-2001_09
Patent number
US06291455B1

Reaction notes

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