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

HRID 249769Notes

Reaction equation

HRID 249769 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+].I[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>CN(C=O)C.O.CCOC(C)=O>[CH2:1]([N:4]1[C:12]2[C:11](=[O:13])[NH:10][C:9](=[O:14])[N:8]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:7]=2[N:6]=[CH:5]1)[CH:2]=[CH2:3]

Participants

7

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 45.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 7-allyl-3,7-dihydro-1H-purine-2,6-dione (10.0 g, 0.052 mol), sodium carbonate (8.3 g, 0.078 mol), and 1-iodopentane (12 g, 0.062 mol) in DMF (100 mL) was stirred at 45° C. for 2 days. The reaction mixture was diluted with water and EtOAc. The aqueous layer was extracted with EtOAc three times. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was treated with ether and the solid formed was filtered to provide the desired product as white solid (6.2 g, 45.4%). LCMS calculated for C13H19N4O2 (M+H): 263.2. found: 263.2.

Workup

  1. extractionThe aqueous layer was extracted with EtOAc three times
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. additionThe residue was treated with ether
  6. customthe solid formed
  7. filtrationwas filtered

Sources & evidence

ORD record
ord-992a00e7f7b1479cab0ce476acf75ff9
Source dataset
uspto-grants-2011_01
Patent number
US07863285B2

Reaction notes

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