Iodoethane → 2,6-dichloro-7-ethyl-7H-purine

HRID 9899

Reaction equation

HRID 9899 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([Cl:11])[N:3]=1.[H-].[Na+].[CH2:14](I)[CH3:15]>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]([CH2:14][CH3:15])[CH:7]=[N:8]2)=[C:4]([Cl:11])[N:3]=1.[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:14][CH3:15])=[C:4]([Cl:11])[N:3]=1

Participants

7

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 53244122,6-Dichloropurine

Product 2

HCID 219882962,6-dichloro-7-ethyl-7H-purineHCID 219883252,6-dichloro-9-ethyl-9H-purine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.0 g (5.29 mmol) of 2,6-dichloro-purine is dissolved in DMF (20 ml) and treated with 152 mg (80%, 5.3 mmol) of sodium hydride and the mixture is stirred at RT for 0.5 hours. After addition of 0.42 ml (5.3 mmol) of ethyl iodide, the mixture is stirred at 70° C. for 3 hours, diluted with ethyl acetate (100 ml) and extracted with concentrated brine. The organic phase is dried (sodium sulfate) and concentrated and the residue is chromatographed (silica gel, methylene chloride:methanol=19:1). An oily mixture comprising 2,6-dichloro-7-ethyl-7H-purine and 2,6-dichloro-9-ethyl-9H-purine is obtained.

Workup

  1. stirringthe mixture is stirred at 70° C. for 3 hours
  2. extractionextracted with concentrated brine
  3. dry with materialThe organic phase is dried (sodium sulfate)
  4. concentrationconcentrated
  5. customthe residue is chromatographed (silica gel, methylene chloride:methanol=19:1)

Sources & evidence

ORD record
ord-66d3e0ffc92349d497cdf78b8c94e762
Source dataset
uspto-grants-2006_08
Patent number
US07091346B1

Linked notes

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