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

HRID 992383Notes

Reaction equation

HRID 992383 reaction equation
C([O:4][C@H:5]([CH3:29])[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][CH2:23][CH2:24][CH2:25][CH2:26][C:27]#[N:28])[C:11]1=[O:12])(=O)C.Cl.O1CCOCC1>CO>[C:27]([CH2:26][CH2:25][CH2:24][CH2:23][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])[CH3:29])[C:11]1=[O:12])#[N:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 54348929(R)-1-(5-acetoxyhexyl)-3-(5-cyanopentyl)-7-methylxanthine

Product 1

HCID 54298528(R)-3-(5-cyanopentyl)-1-(5-hydroxyhexyl)-7-methylxanthineYield 47%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a stirring solution of 0.37 g (R)-1-(5-acetoxyhexyl)-3-(5-cyanopentyl)-7-methylxanthine (0.92 mmol) in 20 ml methanol was added a solution of 4M hydrogen chloride in 70 ml 1,4-dioxane (2.77 mmol). The reaction was heated at reflux (80° C.) for five hours and then cooled to room temperature. The solvent was removed under reduced pressure and the resulting oil was treated with 25 ml saturated aqueous sodium bicarbonate solution and extracted three times with 25 ml dichloromethane. The combined extracts were washed 2× with 25 ml saturated aqueous sodium chloride solution dried over sodium sulfate, and concentrated under vacuum. The resulting residue was purified by flash chromatography eluting with 10% methanol-ethyl acetate to give 0.15 g (R)-3-(5-cyanopentyl)-1-(5-hydroxyhexyl)-7-methylxanthine (47% yield) as a viscous oil.

Workup

  1. temperatureThe reaction was heated
  2. temperaturecooled to room temperature
  3. customThe solvent was removed under reduced pressure
  4. additionthe resulting oil was treated with 25 ml saturated aqueous sodium bicarbonate solution
  5. extractionextracted three times with 25 ml dichloromethane
  6. washThe combined extracts were washed 2× with 25 ml saturated aqueous sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under vacuum
  9. customThe resulting residue was purified by flash chromatography
  10. washeluting with 10% methanol-ethyl acetate

Sources & evidence

ORD record
ord-ca53bfdf778f4f508d8aa9a6d7fa3154
Source dataset
uspto-grants-2002_10
Patent number
US06469017B1

Reaction notes

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