Cesium carbonate → HCID 58280090, compound

HRID 2189094Notes

Reaction equation

HRID 2189094 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:16]([O:18][C:19]4[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=4)[NH2:22])=[N:15][CH:14]=[N:13][C:12]=3[O:11][C:10]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:5][CH:4]=1.[CH3:32][O:33][C:34](=[O:37])[CH2:35]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[CH3:32][O:33][C:34](=[O:37])[CH2:35][NH:22][C:21]1[CH:23]=[CH:24][CH:25]=[C:19]([O:18][C:16]2[C:17]3[C:9]([C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=4)=[C:10]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[O:11][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:20]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 58280122HCID 58280122, compound

Product 1

HCID 58280090HCID 58280090, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Stir 450 mg (1.1 mmol) of 3-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]-oxy}aniline, 202 mg (1.32 mmol) of bromoacetic acid methyl ester and 465.5 mg (1.43 mmol) of caesium carbonate in 10 ml of acetone under reflux overnight. Remove the acetone under reduced pressure and take up the residue in water and extract repeatedly with dichloromethane/ethyl acetate (1:1). Dry the combined organic phases over magnesium sulphate and concentrate. Chromatograph the residue twice on silica gel (eluent: dichloromethane/ethyl acetate 1:1). 75.4 mg (13.8% of theory) of the target compound are obtained as a white foam.

Workup

  1. temperatureunder reflux overnight
  2. customRemove the acetone under reduced pressure
  3. extractionextract repeatedly with dichloromethane/ethyl acetate (1:1)
  4. dry with materialDry the combined organic phases over magnesium sulphate
  5. concentrationconcentrate
  6. custom75.4 mg (13.8% of theory) of the target compound are obtained as a white foam

Sources & evidence

ORD record
ord-5e0c371cff0543c4b7a9ecfe0ca45096
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

Loading…