Sodium hydride → (R)-1-(5-acetoxyhexyl)-3-(5-cyanopentyl)-7-methylxanthine

HRID 992382Notes

Reaction equation

HRID 992382 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:16]2[N:15]=[CH:14][N:13]([CH3:17])[C:12]=2[C:11](=[O:18])[NH:10][C:9]1=[O:19])#[N:2].[H-].[Na+].[C:22]([O:25][C@H:26]([CH3:32])[CH2:27][CH2:28][CH2:29][CH2:30]I)(=[O:24])[CH3:23]>CS(C)=O>[C:22]([O:25][C@H:26]([CH3:32])[CH2:27][CH2:28][CH2:29][CH2:30][N:10]1[C:11](=[O:18])[C:12]2[N:13]([CH3:17])[CH:14]=[N:15][C:16]=2[N:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:1]#[N:2])[C:9]1=[O:19])(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 228882753-(Cyanopentyl)-7-methylxanthineHCID 54009360(R)-5-acetoxy-1-iodohexane

Product 1

HCID 54348929(R)-1-(5-acetoxyhexyl)-3-(5-cyanopentyl)-7-methylxanthineYield 88%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirring solution of 0.31 g 3-(cyanopentyl)-7-methylxanthine (1.2 mmol) in 20 ml dimethyl sulfoxide was added 30 mg sodium hydride (1.3 mmol). After 25 minutes, 0.34 g of (R)-5-acetoxy-1-iodohexane (1.3 mol) was added and the mixture was stirred for 24 h. The mixture was then quenched with 70 ml water and extracted three times with 30 ml ethyl acetate. The combined extracts were washed two times with 35 ml saturated aqueous sodium chloride solution and dried over sodium sulfate, and concentrated under vacuum. The residue was purified by flash chromatography (silica gel) eluting with 5% methanol-ethyl acetate to give 0.42 g (R)-1-(5-acetoxyhexyl)-3-(5-cyanopentyl)-7-methylxanthine (88% yield) as a viscous oil.

Workup

  1. customThe mixture was then quenched with 70 ml water
  2. extractionextracted three times with 30 ml ethyl acetate
  3. washThe combined extracts were washed two times with 35 ml saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by flash chromatography (silica gel)
  7. washeluting with 5% methanol-ethyl acetate

Sources & evidence

ORD record
ord-0b0bc36b8651457693023ee990a9eb9f
Source dataset
uspto-grants-2002_10
Patent number
US06469017B1

Reaction notes

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