Potassium Carbonate → HCID 10710411, compound

HRID 886815Notes

Reaction equation

HRID 886815 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.C(=O)([O-])[O-].[K+].[K+].[F:18][C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:20]=1[CH2:21]Br>CS(C)=O>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:21][C:20]2[C:19]([F:18])=[CH:26][CH:25]=[CH:24][C:23]=2[F:27])=[C:4]([Cl:11])[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5814352-(Bromomethyl)-1,3-difluorobenzeneHCID 53244122,6-Dichloropurine

Product 1

HCID 10710411HCID 10710411, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of 2,6-dichloropurine (5.3 mmol) in 10 ml anhydrous DMSO at room temperature was added anhydrous potassium carbonate (6.34 mmol) and 2,6-difluorobenzylbromide (6.34 mmol). The reaction mixture was maintained at this temperature for 20 hrs. The reaction can be monitored using either TLC or LC/MS. The reaction mixture was poured in to a beaker containing ice-cold water. The aqueous layer was acidified to pH 5-6. Extraction of the aqueous layer, using 3×75 ml portions of ethyl acetate, afforded the crude product. This was purified on the silica gel column (10-70% ethyl acetate in petroleum ether, step-gradient), to give the desired compound in a yield of 61%.

Workup

  1. temperatureThe reaction mixture was maintained at this temperature for 20 hrs
  2. customThe reaction
  3. additionThe reaction mixture was poured in to a beaker
  4. additioncontaining ice-cold water
  5. extractionExtraction of the aqueous layer
  6. customafforded the crude product
  7. customThis was purified on the silica gel column (10-70% ethyl acetate in petroleum ether, step-gradient)

Sources & evidence

ORD record
ord-10d396c0a6b24c75a35d729c1fd4b8a6
Source dataset
uspto-grants-2012_08
Patent number
US08247410B2

Reaction notes

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