Potassium Carbonate → HCID 86659812, compound

HRID 1846329Notes

Reaction equation

HRID 1846329 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH:7]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:26](=[O:27])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=[C:18]2[C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([CH3:35])[CH:29]=2)=[CH:13][CH:12]=1)([CH2:9][CH3:10])[CH3:8].Br[CH2:37][CH2:38][O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41]>CN(C=O)C>[Si:40]([O:39][CH2:38][CH2:37][O:34][C:31]1[CH:32]=[CH:33][C:28]([C:18]2[N:17]([C:14]3[CH:13]=[CH:12][C:11]([CH:7]([CH2:9][CH3:10])[CH3:8])=[CH:16][CH:15]=3)[C:26](=[O:27])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)=[CH:29][C:30]=1[CH3:35])([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 136330824HCID 136330824, compound

Product 1

HCID 86659812HCID 86659812, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

K2CO3 (0.135 g, 0.97 mmol) was added to a solution of 3-(4-sec-butylphenyl)-2-(4-hydroxy-3-methylphenyl)quinazolin-4(3H)-one (0.250 g, 0.65 mmol) in DMF (15 mL). The mixture was stirred at room temperature for 30 min, then (2-bromoethoxy)(tert-butyl)dimethylsilane (0.16 mL, 0.78 mmol) was added and the reaction was heated at reflux temperature for 3 hours, before concentrating in vacuo and dissolving the residue in EtOAc. The organics were washed with saturated NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 2% to 40% EtOAc in heptane, afforded 2-(4-(2-(tert-butyldimethylsilyloxy)-ethoxy)-3-methylphenyl)-3-(4-sec-butylphenyl)quinazolin-4(3H)-one (0.320 g, 90%).

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux temperature for 3 hours
  3. concentrationbefore concentrating in vacuo
  4. dissolutiondissolving the residue in EtOAc
  5. washThe organics were washed with saturated NaHCO3 and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by flash chromatography on silica gel
  10. washeluting with 2% to 40% EtOAc in heptane

Sources & evidence

ORD record
ord-0dff5b4b5fe34f56a278839a90389ebc
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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