7-(Benzyloxy)-4-chloro-6-methoxyquinazoline → 7-Benzyloxy-4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)-6-methoxyquinazoline

HRID 634716Notes

Reaction equation

HRID 634716 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.[F:22][C:23]1[CH:29]=[C:28]([CH3:30])[C:27]([O:31][C:32]([O:34][CH3:35])=[O:33])=[CH:26][C:24]=1[NH2:25]>C(O)(C)C>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:25][C:24]3[CH:26]=[C:27]([O:31][C:32]([O:34][CH3:35])=[O:33])[C:28]([CH3:30])=[CH:29][C:23]=3[F:22])=[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

Participants

4

Reactant 2

HCID 106619987-(Benzyloxy)-4-chloro-6-methoxyquinazolineHCID 226250465-Amino-4-fluoro-2-methylphenyl Methoxyformate

Product 1

HCID 226249317-Benzyloxy-4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)-6-methoxyquinazolineYield 83%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 7-benzyloxy4-chloro-6-methoxyquinazoline (800 mg, 2.6 mmol), (prepared as described for the starting material in Example 4 but with an aqueous work up), and 2-fluoro-5-methoxycarbonyloxy-4-methylaniline (570 mg, 2.89 mmol) in isopropanol (20 ml) was refluxed for 2 hours. After cooling to ambient temperature, the solid was filtered, washed with isopropanol and dried under vacuum to give 7-benzyloxy-4-(2-fluoro-5-methoxycarbonyloxy4-methylanilino)-6-methoxyquinazoline (1.0 g, 77%).

Workup

  1. temperaturewas refluxed for 2 hours
  2. filtrationthe solid was filtered
  3. washwashed with isopropanol
  4. customdried under vacuum

Sources & evidence

ORD record
ord-1d47c0213ce84d63b202c3a75e512916
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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