Allyl bromide → 7-Allyl-8-chloro-1,3-dimethyl-3,7-dihydropurine-2,6-dione

HRID 1791998Notes

Reaction equation

HRID 1791998 reaction equation
[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[N:7]([CH3:12])[C:6](=[O:13])[N:5]([CH3:14])[C:4]=2[N:3]=1.[CH2:15](Br)[CH:16]=[CH2:17].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:17]([N:10]1[C:9]2[C:8](=[O:11])[N:7]([CH3:12])[C:6](=[O:13])[N:5]([CH3:14])[C:4]=2[N:3]=[C:2]1[Cl:1])[CH:16]=[CH2:15]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 106618-ChlorotheophyllineHCID 11430Potassium Carbonate

Product 1

HCID 7386827-Allyl-8-chloro-1,3-dimethyl-3,7-dihydropurine-2,6-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 8-chloro-1,3-dimethyl-3,7-dihydropurine-2,6-dione (10.7 g), allyl bromide (5.2 ml), anhydrous potassium carbonate (10.3 g), and N,N-dimethylformamide (75 ml) was stirred at room temperature overnight. The reaction mixture was extracted with ethyl acetate and water, and the organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and filtered through a small amount of silica gel. The silica gel was washed with ethyl acetate, and the eluate was concentrated under reduced pressure. Recrystallization of the residue from ethyl acetate (50 ml) and hexane (100 ml) gave 10.57 g of the title compound.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate and water
  2. washthe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered through a small amount of silica gel
  5. washThe silica gel was washed with ethyl acetate
  6. concentrationthe eluate was concentrated under reduced pressure
  7. customRecrystallization of the residue from ethyl acetate (50 ml) and hexane (100 ml)

Sources & evidence

ORD record
ord-8be18deaea584ea4b6ab79b4a47d0b61
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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