Sodium Carbonate → HCID 59299587, compound

HRID 2386654Notes

Reaction equation

HRID 2386654 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+].[CH3:22][O:23][CH2:24][CH2:25][O:26][CH2:27]Cl>CN(C=O)C>[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][O:23][CH2:24][CH2:25][O:26][CH3:27])[C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 592995327-Allyl-8-chloro-1H-purine-2,6(3H,7H)-dione

Product 1

HCID 59299587HCID 59299587, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-chloro-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (6 g, 26.5 mmol) in anhydrous DMF (30 ml) was added sodium carbonate (3.09 g, 29.15 mmol). After 10 minutes stirring at room temperature methoxyethoxymethylchloride (3.03 ml, 26.5 mmol) was added and stirring continued under nitrogen at room temperature for 66 hours. The reaction mixture was concentrated in vacuo and the residue dissolved in EtOAc (100 ml) and washed with brine (100 ml), the aqueous extract was extracted with DCM (100 ml) and the organic extracts dried (MgSO4) combined and concentrated in vacuo. The residue was trituated with EtOAc and the solid filtered off. Concentration of the filtrate afforded a light brown oil that was absorbed onto silica and purified by SPE (Si, 50 g) eluting with a gradient of 1:1 EtOAc/cyclohexane-EtOAc to afford the title compound as a white solid (2 g, 24%), m/z 315.2 [MH+]

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe residue dissolved in EtOAc (100 ml)
  4. washwashed with brine (100 ml)
  5. extractionthe aqueous extract
  6. extractionwas extracted with DCM (100 ml)
  7. dry with materialthe organic extracts dried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. filtrationthe solid filtered off
  10. customConcentration of the filtrate afforded a light brown oil that
  11. customwas absorbed onto silica
  12. custompurified by SPE (Si, 50 g)
  13. washeluting with a gradient of 1:1 EtOAc/cyclohexane-EtOAc

Sources & evidence

ORD record
ord-4218bda09f0c4a5bb15dc80ebaadf714
Source dataset
uspto-grants-2012_09
Patent number
US08268839B2

Reaction notes

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