Potassium Carbonate → HCID 86670199, compound

HRID 2401311Notes

Reaction equation

HRID 2401311 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][C:7]([CH:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)=[N:8]2)=[C:4]([Cl:16])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:23][Si:24]([CH3:31])([CH3:30])[CH2:25][CH2:26][O:27][CH2:28]Cl>CN(C=O)C.O>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]([CH2:28][O:27][CH2:26][CH2:25][Si:24]([CH3:31])([CH3:30])[CH3:23])[C:7]([CH:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)=[N:8]2)=[C:4]([Cl:16])[N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 54162597HCID 54162597, compound

Product 1

HCID 86670199HCID 86670199, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture 2,6-dichloro-8-cyclopentyl-7H-purine (0.2 g, 0.78 mmol) and potassium carbonate (0.32 g, 2.34 mmol) was taken in DMF (2.5 ml) and 2-(trimethylsilyl)ethoxymethyl chloride (0.38 g, 2.34 mmol) was added drop wise. The reaction mixture was stirred at room temperature for 4 hours, diluted with water (10 ml). The aqueous layer was extracted with ethyl acetate. The organic layer was washed with saturated brine solution and dried over Na2SO4 and concentrated. The residue was purified by column chromatography to obtain 2,6-dichloro-8-cyclopentyl-7-(2-trimethylsilanyl-ethoxymethyl)-7H-purine (0.12 g, 40%) as yellow oil.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-31afe248c2a94f98970db8816a37929f
Source dataset
uspto-grants-2014_08
Patent number
US08796290B2

Reaction notes

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