Cesium carbonate → 2-(2-(4-Chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethoxy)ethyl benzoate

HRID 1786966Notes

Reaction equation

HRID 1786966 reaction equation
[Cl:1][C:2]1[C:3]2[NH:10][CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:17]([O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30]I)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])O.[Na+]>CN(C)C=O>[C:17]([O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][N:10]1[C:3]2[C:2]([Cl:1])=[N:7][CH:6]=[N:5][C:4]=2[CH:8]=[CH:9]1)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 53706954-chloro-5H-pyrrolo[3,2-d]pyrimidineHCID 213618682-(2-Iodoethoxy)ethyl benzoate

Product 1

HCID 568508032-(2-(4-Chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethoxy)ethyl benzoateYield 55.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (0.659 g) in N,N-dimethylformamide (5.0 mL) was added cesium carbonate (3.13 g) under ice-cooling, and the reaction mixture was stirred while warming to room temperature for 15 min. To the reaction mixture was added 2-(2-iodoethoxy)ethyl benzoate (1.45 g) prepared above, and the mixture was stirred at room temperature for 15 hrs. The reaction mixture was poured into 5% aqueous sodium hydrogen carbonate solution (100 mL), and extracted with ethyl acetate (150 mL×3). The organic layer was washed successively with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was subjected to silica gel chromatography (eluent:hexane/ethyl acetate=95/5→60/40). The object fraction was concentrated under reduced pressure and dried to give the title compound (0.822 g) as a colorless transparent oil.

Workup

  1. temperaturecooling
  2. customprepared above, and the mixture
  3. stirringwas stirred at room temperature for 15 hrs
  4. extractionextracted with ethyl acetate (150 mL×3)
  5. washThe organic layer was washed successively with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. concentrationThe object fraction was concentrated under reduced pressure
  9. customdried

Sources & evidence

ORD record
ord-1e82edd567a44bb9a159177efafbc67a
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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