Sodium hydride → HCID 21890958, compound

HRID 721625Notes

Reaction equation

HRID 721625 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+].Br.[CH2:26]([N:28]([CH2:32][CH3:33])[CH2:29][CH2:30]Br)[CH3:27].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][CH2:27][CH2:26][N:28]([CH2:32][CH3:33])[CH2:29][CH3:30])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 706072-Bromoethyldiethylammonium bromideHCID 516892Sodium BicarbonateHCID 17755504HCID 17755504, compound

Product 1

HCID 21890958HCID 21890958, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]phenol (100 mg) was dissolved in dimethylformamide (2 ml) to prepare a solution. Sodium hydride (27 mg) was then added to the solution, and the mixture was stirred at room temperature for 10 min. 2-(Diethylamino)ethyl bromide hydrobromide (88 mg) was added to the solution, and the mixture was stirred at room temperature for 2 hr. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by thin-layer chromatography using chloroform/methanol for development. Diethyl ether was added to the purification product, and the precipitated crystal was collected by filtration and was washed to give the title compound (30 mg, yield 23%).

Workup

  1. customto prepare a solution
  2. stirringthe mixture was stirred at room temperature for 2 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialwas then dried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation under the reduced pressure
  7. customThe residue was purified by thin-layer chromatography
  8. additionDiethyl ether was added to the purification product
  9. filtrationthe precipitated crystal was collected by filtration
  10. washwas washed

Sources & evidence

ORD record
ord-6d69725a417d47e2a777e19fb5e9d7bd
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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