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

HRID 1791993Notes

Reaction equation

HRID 1791993 reaction equation
[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[NH:7][C:6](=[O:12])[N:5]([CH3:13])[C:4]=2[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:20](Br)[CH:21]=[CH2:22]>CN(C)C=O.C(OCC)(=O)C.O>[CH2:22]([N:10]1[C:9]2[C:8](=[O:11])[NH:7][C:6](=[O:12])[N:5]([CH3:13])[C:4]=2[N:3]=[C:2]1[Cl:1])[CH:21]=[CH2:20]

Participants

7

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 126175848-chloro-3-methyl-2,3,6,9-tetrahydro-1H-purine-2,6-dione

Product 1

HCID 220295197-Allyl-8-chloro-3-methyl-3,7-dihydropurine-2,6-dione

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

8-Chloro-3-methyl-3,7-dihydropurine-2,6-dione (868 mg) and potassium carbonate (628 mg) were suspended in N,N-dimethylformamide (10 ml), and allyl bromide was added dropwise thereto while cooling on ice. After stirring the reaction mixture at room temperature for 17 hours, the resulting white suspension was diluted with ethyl acetate (30 ml) and water (4 ml), and was filtered to give a white solid. The solid was washed with water and ethyl acetate to give 797 mg of the title compound.

Workup

  1. temperaturewhile cooling on ice
  2. filtrationwas filtered
  3. customto give a white solid
  4. washThe solid was washed with water and ethyl acetate

Sources & evidence

ORD record
ord-eba40e1b03a04e9bac81fafb421d9fb6
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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