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

HRID 1420906Notes

Reaction equation

HRID 1420906 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([Cl:20])=[N:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:21][CH3:22])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[F:23][C:24]1[CH:30]=[C:29]([CH3:31])[C:28]([O:32][C:33]([O:35][CH3:36])=[O:34])=[CH:27][C:25]=1[NH2:26]>C(O)(C)C>[ClH:20].[CH2:2]([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:26][C:25]3[CH:27]=[C:28]([O:32][C:33]([O:35][CH3:36])=[O:34])[C:29]([CH3:31])=[CH:30][C:24]=3[F:23])=[N:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:21][CH3:22])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 220308367-(Benzyloxy)-4-chloro-6-methoxyquinazoline hydrochlorideHCID 226250465-Amino-4-fluoro-2-methylphenyl Methoxyformate

Product 1

HCID 226249307-Benzyloxy-4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)-6-methoxyquinazoline hydrochlorideYield 87%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 7-benzyloxy-4-chloro-6-methoxyquinazoline hydrochloride (800 mg, 2.4 mmol), (prepared as described for the starting material in Example 1), and 2-fluoro-5-methoxycarbonyloxy-4-methylaniline (570 mg, 2.89mmol) 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-methoxycarbonyloxy-4-methylanilino)-6-methoxyquinazoline hydrochloride (1.0 g, 87%)

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-53329e1a03c749b3a61c689e85bd6c4f
Source dataset
uspto-grants-2000_06
Patent number
US06071921

Reaction notes

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