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

HRID 361880

Reaction equation

HRID 361880 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-purineYield 45%

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 (3×50 mL). The organic extracts were combined and back washed with 3×50 mL of waterfollowed 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 0.37 gms of desired N-9 product (45%) and 0.08 gms of the N-7 isomer(10%).

Workup

  1. customThe reaction was quenched with 30 mL of water
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washback washed with 3×50 mL of waterfollowed by 20 mL of brine
  4. dry with materialThe ethyl acetate solution was dried over anhydrous magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-9a0d011c5c81437dbbce13410c0cc588
Source dataset
uspto-grants-1999_02
Patent number
US05866702

Linked notes

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