Isopropyl iodide → 2,6-dichloro-9-(propan-2-yl)-9H-purine

HRID 2215651Notes

Reaction equation

HRID 2215651 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+].[H][H].[CH:16](I)([CH3:18])[CH3:17]>CN(C=O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:16]([CH3:18])[CH3:17])=[C:4]([Cl:11])[N:3]=1

Participants

6

Reactant 4

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 53244122,6-DichloropurineHCID 178418361HCID 178418361, compound

Product 1

HCID 112184902,6-dichloro-9-(propan-2-yl)-9H-purine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.67 g of 2,6-dichloropurine in 5 mL of dry DMF at room temperature was added 0.16 gms (1.1 eq.) of 50% sodium hydride/oil powder. Upon cessation of hydrogen evolution, a large excess (2 mL) of isopropyl iodide was added to the anionic solution. This reaction solution was stirred for three days at ambient temperature. The reaction was quenched with 30 mL of water and extracted with ethyl acetate (350 mL). The organic extracts were combined and back washed with 350 mL of water followed by 20 mL of brine. The ethyl acetate solution was dried over anhydrous magnesium sulfate and evaporated. The compound was subjected to variable gradient flash chromatography on silica gel with hexane/ethyl acetate mixtures and yielded the N-9 product and the N-7 isomer.

Workup

  1. customThe reaction was quenched with 30 mL of water
  2. extractionextracted with ethyl acetate (350 mL)
  3. washback washed with 350 mL of water
  4. dry with materialThe ethyl acetate solution was dried over anhydrous magnesium sulfate
  5. customevaporated
  6. customyielded the N-9 product

Sources & evidence

ORD record
ord-a06b9c1ba97b4187a14f8b4bf9ec85ba
Source dataset
uspto-grants-2006_09
Patent number
US07109330B2

Reaction notes

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