Iodoethane → 7-Allyl-3-ethyl-xanthine

HRID 2200632Notes

Reaction equation

HRID 2200632 reaction equation
[CH2:1]([N:4]1[C:12]2[C:11](=[O:13])[NH:10][C:9](=[O:14])[NH:8][C:7]=2[N:6]=[CH:5]1)[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].I[CH2:22][CH3:23]>CN(C=O)C>[CH2:1]([N:4]1[C:12]2[C:11](=[O:13])[NH:10][C:9](=[O:14])[N:8]([CH2:22][CH3:23])[C:7]=2[N:6]=[CH:5]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 598537957-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione

Product 1

HCID 198196497-Allyl-3-ethyl-xanthineYield 71.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-allyl-1H-purine-2,6(3H,7H)-dione (15 g, 78.13 mmol) in DMF (200 mL) was added potassium carbonate (23.7 g, 171.74 mmol), followed by dropwise addition of iodoethane (3.6 mL, 44.54 mmol). The reaction was stirred at room temperature overnight. The reaction was concentrated and partitioned between ethyl acetate and water. The organic phase was washed with brine and dried over sodium sulfate, and concentrated to give a crude product which was purified by silica gel chromatography eluting with petroleum/ethyl acetate (6:1 to 3:1) to give 7-allyl-3-ethyl-1H-purine-2,6(3H,7H)-dione (7 g, 40.7% yield) as yellow solid. LCMS retention time 0.402 min; LCMS MH+ 221.

Workup

  1. concentrationThe reaction was concentrated
  2. custompartitioned between ethyl acetate and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customto give a crude product which
  7. customwas purified by silica gel chromatography
  8. washeluting with petroleum/ethyl acetate (6:1 to 3:1)

Sources & evidence

ORD record
ord-50f936227d7c4018a80cd20d45575559
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

Loading…