Methyl iodide → 1-methyl-3-pentyl-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione

HRID 2386621Notes

Reaction equation

HRID 2386621 reaction equation
[CH2:1]([N:6]1[C:14]2[N:13]=[CH:12][N:11]([CH2:15][CH:16]=[CH2:17])[C:10]=2[C:9](=[O:18])[NH:8][C:7]1=[O:19])[CH2:2][CH2:3][CH2:4][CH3:5].[C:20](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[CH3:20][N:8]1[C:9](=[O:18])[C:10]2[N:11]([CH2:15][CH:16]=[CH2:17])[CH:12]=[N:13][C:14]=2[N:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[C:7]1=[O:19]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 598538107-Allyl-3-pentyl-3,7-dihydro-1H-purine-2,6-dione

Product 1

HCID 592995971-methyl-3-pentyl-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dioneYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Pentyl-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (0.20 g, 0.76 mmol), potassium carbonate (0.4 g, 2.9 mmol) and methyl iodide (0.5 ml, 4.9 mmol) were stirred and heated at 50° C. in DMF (5 ml) for 3 h. The solution was allowed to cool and separated between ethyl acetate and brine. The organics were isolated, dried (MgSO4) and concentrated to provide the title compound (0.21 g, 100%). m/z 277 [MH+]

Workup

  1. temperatureto cool
  2. customseparated between ethyl acetate and brine
  3. customThe organics were isolated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-878fb279a189472ca8c4fa62aabebb58
Source dataset
uspto-grants-2012_09
Patent number
US08268839B2

Reaction notes

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