Water → HCID 9947912, compound

HRID 1814959Notes

Reaction equation

HRID 1814959 reaction equation
[C-:1]#[N:2].[K+].CS(O[C@@H:9]([CH3:27])[CH2:10][CH2:11][CH2:12][CH2:13][N:14]1[C:23](=[O:24])[C:22]2[N:21]([CH3:25])[CH:20]=[N:19][C:18]=2[N:17]([CH3:26])[C:15]1=[O:16])(=O)=O.O>CS(C)=O>[C:1]([C@H:9]([CH3:27])[CH2:10][CH2:11][CH2:12][CH2:13][N:14]1[C:23](=[O:24])[C:22]2[N:21]([CH3:25])[CH:20]=[N:19][C:18]=2[N:17]([CH3:26])[C:15]1=[O:16])#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 54003857HCID 54003857, compound

Product 1

HCID 9947912HCID 9947912, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

Potassium cyanide (280 mg, 4.30 mmol) was added to a solution of (5)-1-(5-methanesulfonyloxyhexyl)-3,7-dimethylxanthine (prepared as described for CT11558) (770 mg, 2.15 mmol) in dimethylsulfoxide (10 ml). After heating at 50° C. for 24 hours, the mixture was poured into water (50 ml) and extracted with ethyl acetate (3x 50 ml). The combined extracts were washed with water (40 ml), saturated aqueous sodium chloride solution (40 ml), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate to provide (R)-1-(5-cyanohexyl)-3,7-dimethylxanthine (CT16575) (280 mg).

Workup

  1. extractionextracted with ethyl acetate (3x 50 ml)
  2. washThe combined extracts were washed with water (40 ml), saturated aqueous sodium chloride solution (40 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-111b892535104400bff054245485085d
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

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