Sodium Carbonate → 7-Allyl-3-pentyl-3,7-dihydro-1H-purine-2,6-dione

HRID 1943804Notes

Reaction equation

HRID 1943804 reaction equation
[CH2:1]([N:4]1[C:12]2[C:11](=[O:13])[NH:10][C:9](=[O:14])[NH:8][C:7]=2[N:6]=[CH:5]1)[CH:2]=[CH2:3].C(=O)([O-])[O-].[Na+].[Na+].[CH2:21](I)[CH2:22][CH2:23][CH2:24][CH3:25]>CN(C=O)C>[CH2:21]([N:8]1[C:7]2[N:6]=[CH:5][N:4]([CH2:1][CH:2]=[CH2:3])[C:12]=2[C:11](=[O:13])[NH:10][C:9]1=[O:14])[CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 123351-IodopentaneHCID 598537957-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione

Product 1

HCID 598538107-Allyl-3-pentyl-3,7-dihydro-1H-purine-2,6-dioneYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (0.61 g, 3.2 mmol), sodium carbonate (0.60 g, 5.7 mmol) and pentyl iodide (0.64 g, 3.2 mmol) were stirred in DMF (5 ml) at 50° C. for 18 h. The solution was cooled, separated between ethyl acetate and brine and the organics isolated, dried (MgSO4) and concentrated. Chromatography over silica (gradient elution dichloromethane to 5:1 dichloromethane/ethyl acetate) provided the title compound as a pale yellow solid (0.47 g, 56%). m/z 263[MH+]

Workup

  1. temperatureThe solution was cooled
  2. customseparated between ethyl acetate and brine
  3. dry with materialthe organics isolated, dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-64f3f45561d644559a647ebfc4a8d154
Source dataset
uspto-grants-2013_03
Patent number
US08394808B2

Reaction notes

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