Potassium Carbonate → HCID 53813730, compound

HRID 1195431Notes

Reaction equation

HRID 1195431 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([N:11]([CH3:13])[CH3:12])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23]Br>CN(C)C=O>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:23][C:22]2[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=2[F:20])=[C:4]([N:11]([CH3:13])[CH3:12])[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67968alpha-Bromo-o-fluorotolueneHCID 178483050HCID 178483050, compound

Product 1

HCID 53813730HCID 53813730, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.31 g (16.8 mmol) of 2-chloro-6-(N,N-dimethylamino)-9H-purine are dissolved in 60 ml of N,N-dimethylformamide. 4.16 g (30.2 mmol) of potassium carbonate and 2.02 ml (16.8 mmol) of 2-fluorobenzyl bromide are added to the solution. The reaction mixture is then stirred for 3 hours at room temperature and then ice water is added and the whole is extracted three times with dichloromethane. The combined organic phases are washed twice with water, dried over magnesium sulfate and concentrated by evaporation. The residue is chromatographed on silica gel with toluene/ethyl acetate (3:1) as eluant. The eluate is concentrated by evaporation and the residue obtained is recrystallised from ethyl acetate/diethyl ether. In this manner 2-chloro-6-(N,N-dimethylamino)-9-(2-fluorobenzyl)-9H-purine is obtained in the form of colourless needles having a melting range of from 130° to 131°.

Workup

  1. extractionthe whole is extracted three times with dichloromethane
  2. washThe combined organic phases are washed twice with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated by evaporation
  5. customThe residue is chromatographed on silica gel with toluene/ethyl acetate (3:1) as eluant
  6. concentrationThe eluate is concentrated by evaporation
  7. customthe residue obtained
  8. customis recrystallised from ethyl acetate/diethyl ether

Sources & evidence

ORD record
ord-8bbdfe377f434a6b9e95b8a61b6d56bb
Source dataset
uspto-grants-1992_05
Patent number
US05110818

Reaction notes

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