Sodium Carbonate → 7-Allyl-8-chloro-3-pentyl-1H-purine-2,6(3H,7H)-dione

HRID 2386611Notes

Reaction equation

HRID 2386611 reaction equation
[Cl:1][C:2]1[N:10]([CH2:11][CH:12]=[CH2:13])[C:9]2[C:8](=[O:14])[NH:7][C:6](=[O:15])[NH:5][C:4]=2[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:22](I)[CH2:23][CH2:24][CH2:25][CH3:26]>CN(C=O)C.O>[Cl:1][C:2]1[N:10]([CH2:11][CH:12]=[CH2:13])[C:9]2[C:8](=[O:14])[NH:7][C:6](=[O:15])[N:5]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:4]=2[N:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 123351-IodopentaneHCID 592995327-Allyl-8-chloro-1H-purine-2,6(3H,7H)-dione

Product 1

HCID 592995577-Allyl-8-chloro-3-pentyl-1H-purine-2,6(3H,7H)-dioneYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-chloro-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (100 mg, 0.44 mmol) in anhydrous DMF (3 ml) was added sodium carbonate (0.051 g, 0.484 mmol). After 10 minutes stirring at room temperature pentyl iodide (0.063 ml, 0.484 mmol) was added and stirring continued under nitrogen at room temperature for 18 hours. The reaction mixture was diluted with water (25 ml) and extracted with EtOAc (2×25 ml). The combined organic extracts were dried (MgSO4) filtered and evaporated. Purification by SPE (Si, 5 g) eluting with 4:1 EtOAc/cyclohexane afforded the title compound as a white solid (96 mg, 74%); m/z 297.2 [MH+].

Workup

  1. additionwas added
  2. extractionextracted with EtOAc (2×25 ml)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by SPE (Si, 5 g)
  7. washeluting with 4:1 EtOAc/cyclohexane

Sources & evidence

ORD record
ord-5fce89ea592b45fba7e0e3389ea550a0
Source dataset
uspto-grants-2012_09
Patent number
US08268839B2

Reaction notes

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