Water → HCID 86616377, compound

HRID 545122Notes

Reaction equation

HRID 545122 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[Cl:14][C:15]1[N:24]=[C:23](Cl)[C:22]2[C:17](=[CH:18][C:19]([O:28][CH3:29])=[C:20]([O:26][CH3:27])[CH:21]=2)[N:16]=1.O>O1CCOCC1>[Cl:14][C:15]1[N:24]=[C:23]([CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])[C:22]2[C:17](=[CH:18][C:19]([O:28][CH3:29])=[C:20]([O:26][CH3:27])[CH:21]=2)[N:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 5203272,4-Dichloro-6,7-dimethoxyquinazoline

Product 1

HCID 86616377HCID 86616377, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Diethyl malonate (0.76 mL) was dissolved in dioxane (25 mL), sodium hydride (200 mg) was added, and the mixture was stirred at room temperature for 30 min. Then, 2,4-dichloro-6,7-dimethoxyquinazoline (1.3 g) was added, and the mixture was heated under reflux for 3.5 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was recrystallized from a mixed solvent of ethyl acetate and hexane to give the title compound (840 mg) as a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3.5 hrs
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was recrystallized from a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-c7dbf9673ae14c1a898b85e0886feedb
Source dataset
uspto-grants-2011_05
Patent number
US07935700B2

Reaction notes

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