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

HRID 1786972Notes

Reaction equation

HRID 1786972 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]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][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 125101182-Iodoethyl Benzoate

Product 1

HCID 568506702-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethyl benzoateYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (141 mg) in N,N-dimethylformamide (2.5 mL) was added cesium carbonate (358 mg) under ice-cooling, and the reaction mixture was stirred while warming to room temperature for 15 min. To the reaction mixture was added 2-iodoethyl benzoate (298 mg), and the mixture was stirred at room temperature for 15 hrs. The reaction mixture was poured into 5% aqueous sodium hydrogen carbonate solution (50 mL), and extracted with ethyl acetate (50 mL×3). The organic layer 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 2-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethyl benzoate (205 mg) as a colorless transparent oil.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 15 hrs
  3. extractionextracted with ethyl acetate (50 mL×3)
  4. washThe organic layer washed successively with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. concentrationThe object fraction was concentrated under reduced pressure
  8. customdried

Sources & evidence

ORD record
ord-773dab546a1b4512929373d9e453fda4
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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