Methyl iodide → HCID 59299571, compound

HRID 2386625Notes

Reaction equation

HRID 2386625 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])[N:5]([CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])[C:4]=2[N:3]=1.[C:22](=O)([O-])[O-].[Na+].[Na+].CI>CN(C=O)C>[Cl:1][C:2]1[N:10]([CH2:11][CH:12]=[CH2:13])[C:9]2[C:8](=[O:14])[N:7]([CH3:22])[C:6](=[O:15])[N:5]([CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])[C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 59299587HCID 59299587, compound

Product 1

HCID 59299571HCID 59299571, compoundYield 142.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-chloro-3-({[2-(methyloxy)ethyl]oxy}methyl)-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (2 g, 6.37 mmol) in anhydrous DMF (15 ml) was added sodium carbonate (0.743 g, 7 mmol). After 10 minutes stirring at room temperature methyliodide (0.44 ml, 7 mmol) was added and stirring continued under nitrogen at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and the residue dissolved in EtOAc (100 ml) and washed with brine (100 ml). The organic extract was dried (MgSO4) filtered and evaporated to afford the title compound as a tan oil (85% pure) (2.98 g, quant.), m/z 329.2 [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 organic extract
  6. dry with materialwas dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-4cb883d4a3324f88ab4d8b44dbb65783
Source dataset
uspto-grants-2012_09
Patent number
US08268839B2

Reaction notes

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