HCID 53837538, compound → HCID 11500313, compound

HRID 1835720Notes

Reaction equation

HRID 1835720 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](COCC)[C:16]([NH:25][CH3:26])=[N:15][C:14]=2[N:13]([CH3:27])[C:11]1=[O:12])(=O)C>CO.Cl>[OH:4][C@H:5]([CH3:28])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[NH:17][C:16]([NH:25][CH3:26])=[N:15][C:14]=2[N:13]([CH3:27])[C:11]1=[O:12]

Participants

4

Reactant 1

HCID 53837538HCID 53837538, compound

Product 1

HCID 11500313HCID 11500313, compoundYield 41.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

A solution of (R)-1-(5-acetoxyhexyl)-7-ethoxymethyl-3-methyl-8-methylaminoxanthine (0.32 g) in methanol (10 ml) was heated in presence of concentrated hydrochloric acid (2 drops) for 12 hours to 70° C. After evaporation of the solvent under reduced pressure, the residue was dissolved in 20% methanol-ethyl acetate (50 ml). The solution was washed with saturated sodium bicarbonate solution (20 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with 10% methanol-ethyl acetate to provide (R)-1-(5-hydroxyhexyl)-3-methyl-8-methylaminoxanthine (0.100 g).

Workup

  1. customAfter evaporation of the solvent under reduced pressure
  2. dissolutionthe residue was dissolved in 20% methanol-ethyl acetate (50 ml)
  3. washThe solution was washed with saturated sodium bicarbonate solution (20 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel eluting with 10% methanol-ethyl acetate

Sources & evidence

ORD record
ord-0b5b8fa8373340cf9b6874046d3b5699
Source dataset
uspto-grants-2004_08
Patent number
US06774130B2

Reaction notes

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