Reaction #336944

Reaction equation

7-Benzyl-3,7-dihydro-1H-purine-2,6-dione

sodium carbonate

1-iodopentane

→

desired product

Yield 44.0%

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

Yield 44.0%

Solvents

water

EtOAc

DMF

Conditions

Workup

1. 1
   ExtractionThe aqueous layer was extracted with EtOAc twice
2. 2
   OtherThe combined organic layers were dried
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated
5. 5
   OtherThe resulting white solid was collected
6. 6
   Otherdried in vacuum oven at 50° C. for 18 h

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.

Source