Potassium Carbonate → 2,6-Dichloro-9-cyclopropylpurine

HRID 570558Notes

Reaction equation

HRID 570558 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+].[CH:18]1(I)[CH2:20][CH2:19]1>CS(C)=O>[CH:18]1([N:8]2[CH:7]=[N:6][C:5]3[C:9]2=[N:10][C:2]([Cl:1])=[N:3][C:4]=3[Cl:11])[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 640653IodocyclopropaneHCID 53244122,6-Dichloropurine

Product 1

HCID 836813712,6-Dichloro-9-cyclopropylpurineYield 35%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2,6-Dichloropurine (1 mmol), powdered potassium carbonate (4 mmol) and cyclopropyliodide were vigorously stirred in 5 mL DMSO overnight. After evaporation of the solvent the product was extracted (water/diethylether) and purified by column chromatography (silicagel/1% MeOH in CHCl3). Crystallization from diethylether gave product in 35% yield, mp 121-124° C.

Workup

  1. customAfter evaporation of the solvent the product
  2. extractionwas extracted (water/diethylether)
  3. custompurified by column chromatography (silicagel/1% MeOH in CHCl3)
  4. customCrystallization from diethylether
  5. customgave product in 35% yield, mp 121-124° C.

Sources & evidence

ORD record
ord-20cd74ffb7cb48129122e08aefcfdb27
Source dataset
uspto-grants-2015_05
Patent number
US09023857B2

Reaction notes

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