Potassium Carbonate → 2-(4-(2-(tert-Butyldimethylsilyloxy)ethoxy)-3-methylphenyl)-3-(4-chlorophenyl)quinazolin-4(3H)-one

HRID 1846332Notes

Reaction equation

HRID 1846332 reaction equation
C([O-])([O-])=O.[K+].[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=[C:15]2[C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([CH3:32])[CH:26]=2)=[CH:10][CH:9]=1.Br[CH2:34][CH2:35][O:36][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38]>CN(C=O)C>[Si:37]([O:36][CH2:35][CH2:34][O:31][C:28]1[CH:29]=[CH:30][C:25]([C:15]2[N:14]([C:11]3[CH:10]=[CH:9][C:8]([Cl:7])=[CH:13][CH:12]=3)[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)=[CH:26][C:27]=1[CH3:32])([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 1363309563-(4-chlorophenyl)-2-(4-hydroxy-3-methylphenyl)quinazolin-4(3H)-one

Product 1

HCID 674598262-(4-(2-(tert-Butyldimethylsilyloxy)ethoxy)-3-methylphenyl)-3-(4-chlorophenyl)quinazolin-4(3H)-oneYield 103.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

K2CO3 (0.131 g, 0.95 mmol) was added to a solution of 3-(4-chlorophenyl)-2-(4-hydroxy-3-methylphenyl)quinazolin-4(3H)-one (0.230 g, 0.63 mmol) in DMF (15 mL) and stirred for 30 min. (2-Bromoethoxy)(tert-butyl)dimethylsilane (0.16 mL, 0.76 mmol) was added and the reaction was heated to reflux temperature for 3 hours, and concentrated in vacuo. The residue was dissolved in EtOAc, washed with saturated NaHCO3, and then brine, dried (Na2SO4), filtered, and concentrated in vacuo, to afford 2-(4-(2-(tert-Butyldimethylsilyloxy)ethoxy)-3-methylphenyl)-3-(4-chlorophenyl)quinazolin-4(3H)-one (0.340 g, quantitative).

Workup

  1. additionwas added
  2. temperaturethe reaction was heated
  3. temperatureto reflux temperature for 3 hours
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in EtOAc
  6. washwashed with saturated NaHCO3
  7. dry with materialbrine, dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-801cf4297e3d44a882c630a22b58114c
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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