Sodium hydride → HCID 21890086, compound

HRID 721597Notes

Reaction equation

HRID 721597 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.[H-].[Na+].[CH3:25][O:26][C:27](=[O:30])[CH2:28]Br.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:28][C:27]([O:26][CH3:25])=[O:30])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 516892Sodium BicarbonateHCID 17755504HCID 17755504, compound

Product 1

HCID 21890086HCID 21890086, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]phenol (100 mg) was dissolved in dimethylformamide (2 ml) to prepare a solution. Sodium hydride (15 mg) was added to the solution, and the mixture was stirred at 0° C. for 10 min. Methylbromoacetate (0.037 ml) was added thereto, and the mixture was further stirred at 0° C. for 30 min. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the mixture was extracted with ethyl acetate, followed by washing with saturated brine. The extract was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. Diethyl ether was added to the residue, and the precipitated crystal was collected by filtration and was washed to give the title compound (88 mg, yield 71%).

Workup

  1. customto prepare a solution
  2. stirringthe mixture was further stirred at 0° C. for 30 min
  3. extractionthe mixture was extracted with ethyl acetate
  4. washby washing with saturated brine
  5. dry with materialThe extract was then dried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation under the reduced pressure
  7. additionDiethyl ether was added to the residue
  8. filtrationthe precipitated crystal was collected by filtration
  9. washwas washed

Sources & evidence

ORD record
ord-7d79834700cd470eb3a3092001cfd399
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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