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

HRID 2374300Notes

Reaction equation

HRID 2374300 reaction equation
[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[NH:14][C:13](=[O:18])[NH:12][C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].I[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>CN(C=O)C.O.CCOC(C)=O>[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[NH:14][C:13](=[O:18])[N:12]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 123351-IodopentaneHCID 125005077-Benzyl-1H-purine-2,6(3H,7H)-dione

Product 1

HCID 598538537-Benzyl-3-pentyl-3,7-dihydro-1H-purine-2,6-dioneYield 44%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

7-Benzyl-3,7-dihydro-1H-purine-2,6-dione (5.0 g, 21 mmol) was mixed with sodium carbonate (3.3 g, 31 mmol) and 1-iodopentane (4.0 mL, 31 mmol) in DMF (60 mL). After being stirred at 40° C. for 18 h, the reaction mixture was diluted with water and EtOAc. The aqueous layer was extracted with EtOAc twice. The combined organic layers were dried, filtered and concentrated. The resulting white solid was collected and dried in vacuum oven at 50° C. for 18 h to provide the desired product (2.84 g, 44% yield). LCMS calculated for C17H21N4O2 (M+H): 313.2; found: 313.2.

Workup

  1. extractionThe aqueous layer was extracted with EtOAc twice
  2. customThe combined organic layers were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting white solid was collected
  6. customdried in vacuum oven at 50° C. for 18 h

Sources & evidence

ORD record
ord-d961f90bd17c400fb9432fbf4e690936
Source dataset
uspto-grants-2008_12
Patent number
US07462624B2

Reaction notes

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