Sodium Hydroxide → 7-(Benzyloxy)-4-chloro-6-methoxyquinazoline

HRID 1375774Notes

Reaction equation

HRID 1375774 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH2:6]([O:13][C:14]1[CH:23]=[C:22]2[C:17]([C:18](=O)[NH:19][CH:20]=[N:21]2)=[CH:16][C:15]=1[O:25][CH3:26])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(C(C)C)CC)(C)C.[OH-].[Na+]>>[CH2:6]([O:13][C:14]1[CH:23]=[C:22]2[C:17]([C:18]([Cl:3])=[N:19][CH:20]=[N:21]2)=[CH:16][C:15]=1[O:25][CH3:26])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 1354047187-Benzyloxy-6-methoxy-3H-quinazolin-4-one

Product 1

HCID 106619987-(Benzyloxy)-4-chloro-6-methoxyquinazolineYield 99%

Procedure

Phosphorus oxychloride (515 ml) was added to 7-(benzyloxy)-6-methoxy-3,4-dihydro-4-quinazolinone (400 mg) and diisopropylethylamine (0.3 ml), and the mixture was refluxed for 20 min. The reaction solution was cooled to room temperature. A 10% aqueous sodium hydroxide solution was then added to the reaction solution, followed by extraction with chloroform. The organic layer was dried over sodium sulfate. The organic layer was filtered, and the solvent was then removed by distillation under the reduced pressure. The residue was dried through a vacuum pump to give 420 mg (yield 99%) of the title compound.

Workup

  1. temperaturethe mixture was refluxed for 20 min
  2. extractionfollowed by extraction with chloroform
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationThe organic layer was filtered
  5. customthe solvent was then removed by distillation under the reduced pressure
  6. customThe residue was dried through a vacuum pump

Sources & evidence

ORD record
ord-5d08b6f8359a4ebd9b5d58a10e5cc91c
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

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