Potassium Carbonate → 4-(6-Chloro-purin-9-yl)-butyric acid ethyl ester

HRID 854246Notes

Reaction equation

HRID 854246 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.C(=O)([O-])[O-].[K+].[K+].[CH2:17]([O:19][C:20](=[O:25])[CH2:21][CH2:22][CH2:23]Br)[CH3:18]>CN(C)C=O>[CH2:17]([O:19][C:20](=[O:25])[CH2:21][CH2:22][CH2:23][N:6]1[CH:5]=[N:4][C:3]2[C:7]1=[N:8][CH:9]=[N:10][C:2]=2[Cl:1])[CH3:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 53592776-Chloropurine

Product 1

HCID 155472644-(6-Chloro-purin-9-yl)-butyric acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

25 g (0.162 mol) of 6-chloropurine was dissolved in 500 ml of dimethylformamide and 89.4 g (0.647 mol) of potassium carbonate was added to this solution. 23.4 ml (0.162 mol) of 4-bromobutyric acid ethyl ester was added dropwise over a period of 4 hours. The solution was stirred for 16 h at room temperature. The solvent was removed in vacuo, the residue was dissolved in EE and the solution was washed three times with water and once with saturated aqueous sodium chloride solution. The organic phase was dried with sodium sulfate, filtered and the solvent was removed in vacuo. The residue was chromatographed on silica gel eluting with DCM/EE (1/1). Yield: 28.7 g.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in EE
  3. washthe solution was washed three times with water
  4. dry with materialThe organic phase was dried with sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customThe residue was chromatographed on silica gel eluting with DCM/EE (1/1)

Sources & evidence

ORD record
ord-5ad8221b7c3249f9934d4b27df3b9a87
Source dataset
uspto-grants-2007_08
Patent number
US07259159B2

Reaction notes

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