HCID 53837538, compound → HCID 11500313, compound

HRID 1814933Notes

Reaction equation

HRID 1814933 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-3fddcfad9bc54303a8a7d5d4f39ada03
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

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