Sodium hydride → HCID 15896334, compound

HRID 479460Notes

Reaction equation

HRID 479460 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:30]=[CH:31][CH:32]=1)[CH2:6][N:7]1[CH2:12][CH2:11][CH:10]([N:13]2[CH:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][C:14]2=[O:29])[CH2:9][CH2:8]1.[H-].[Na+].[Si:35]([O:42][CH2:43][CH2:44]Br)([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36].C(=O)(O)[O-].[Na+]>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Si:35]([O:42][CH2:43][CH2:44][N:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:22]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:13]([CH:10]2[CH2:11][CH2:12][N:7]([CH2:6][C:5]3[CH:30]=[CH:31][CH:32]=[C:3]([CH2:2][OH:1])[CH:4]=3)[CH2:8][CH2:9]2)[C:14]1=[O:29])([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 15896333HCID 15896333, compound

Product 1

HCID 15896334HCID 15896334, compoundYield 34.2%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 200 mg (0.468 mmol) of 3-[1-(3-hydroxymethylbenzyl) piperidin-4-yl]-4-phenyl-3,4-dihydro-2(1H)-quinazolinone in 3 ml of DMF, 22 mg (0.55 mmol) of sodium hydride (60%) were added under ice-cooling and stirred at the same temperature for 5 minutes and at room temperature for 10 minutes. After ice-cooling again, 224 mg (0.55 mmol) of 2-tert-butyldimethylsilyloxyethylbromide and 2 mg of tetrabutylammonium iodide were added thereto and stirred under ice-cooling for 4 hours. It was poured into aqueous sodium bicarbonate solution, extracted with ethyl acetate, washed with water, aqueous saturated sodium bicarbonate solution and saturated brine, and dried over anhydrous sodium sulfate. After the solvent was evaporated under reduced pressure, the obtained residue was purified by silica gel column chromatography (chloroform—3% methanol/chloroform) to give 92 mg (0.16 mmol) of the title compound as colorless oil.

Workup

  1. temperaturecooling
  2. temperatureAfter ice-cooling again
  3. stirringstirred under ice-
  4. temperaturecooling for 4 hours
  5. extractionextracted with ethyl acetate
  6. washwashed with water, aqueous saturated sodium bicarbonate solution and saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customAfter the solvent was evaporated under reduced pressure
  9. customthe obtained residue was purified by silica gel column chromatography (chloroform—3% methanol/chloroform)

Sources & evidence

ORD record
ord-e3624859616f4f6e917849abcc742026
Source dataset
uspto-grants-2003_11
Patent number
US06645971B1

Reaction notes

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