Hydrochloric Acid → (R)-3-(2-furylmethyl)-1-(5-hydroxyhexyl)-7-methylxanthine

HRID 1835708Notes

Reaction equation

HRID 1835708 reaction equation
C([O:4][C@H:5]([CH3:28])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH3:21])[CH:16]=[N:15][C:14]=2[N:13]([CH2:22][C:23]2[O:24][CH:25]=[CH:26][CH:27]=2)[C:11]1=[O:12])(=O)C.Cl.O1CCOCC1>CO>[O:24]1[CH:25]=[CH:26][CH:27]=[C:23]1[CH2:22][N:13]1[C:14]2[N:15]=[CH:16][N:17]([CH3:21])[C:18]=2[C:19](=[O:20])[N:10]([CH2:9][CH2:8][CH2:7][CH2:6][C@H:5]([OH:4])[CH3:28])[C:11]1=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 54209961(R)-1-(5-acetoxyhexyl)-3-(2-furylmethyl)-7-methylxanthine

Product 1

HCID 9884609(R)-3-(2-furylmethyl)-1-(5-hydroxyhexyl)-7-methylxanthineYield 80.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring solution of (R)-1-(5-acetoxyhexyl)-3-(2-furylmethyl)-7-methylxanthine (0.42 g, 1.07 mmol) in methanol (20 ml) was added a solution of hydrogen chloride in 1,4-dioxane (4 M, 0.80 ml, 3.21 mmol) and the mixture was refluxed for 5 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure. The residue was treated with saturated aqueous sodium bicarbonate solution (25 ml) and the mixture was extracted with dichloromethane (3×25 ml). The combined extracts were washed with saturated aqueous sodium chloride solution (2×25 ml), dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate to provide (R)-3-(2-furylmethyl)-1-(5-hydroxyhexyl)-7-methylxanthine (0.30 g, 80% yield).

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. customthe solvent was evaporated under reduced pressure
  3. additionThe residue was treated with saturated aqueous sodium bicarbonate solution (25 ml)
  4. extractionthe mixture was extracted with dichloromethane (3×25 ml)
  5. washThe combined extracts were washed with saturated aqueous sodium chloride solution (2×25 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-168ed2dfb5e140d8ae676b9b1c400d04
Source dataset
uspto-grants-2004_08
Patent number
US06774130B2

Reaction notes

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