Sodium hydride → 3-(Cyanopentyl)-7-methylxanthine

HRID 992380

Reaction equation

HRID 992380 reaction equation
[CH3:1][N:2]1[C:10]2[C:9](=[O:11])[NH:8][C:7](=[O:12])[NH:6][C:5]=2[N:4]=[CH:3]1.[H-].[Na+].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]#[N:22]>CS(C)=O>[C:21]([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:6]1[C:5]2[N:4]=[CH:3][N:2]([CH3:1])[C:10]=2[C:9](=[O:11])[NH:8][C:7]1=[O:12])#[N:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 683747-MethylxanthineHCID 810936-Bromohexanenitrile

Product 1

HCID 228882753-(Cyanopentyl)-7-methylxanthineYield 15.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirring slurry of 2.69 g 7-methylxanthine (16.2 mmol) (Aldrich, Milwaukee, Wis.) in 50 ml methyl sulfoxide was added 0.39 g sodium hydride (16.2 mmol). After 1 hour, 2.85 g of 6-bromocapronitrile (16.2 mmol) (Lancaster Synthesis, Inc., Windham, N.H.) was added neat and the reaction was stirred for 72 h at room temperature. The mixture was then quenched with 150 mL water and extracted five times with 35 ml methyl acetate. The combined extracts were washed two times with 40 ml saturated aqueous sodium bicarbonate solution and two times with 40 ml saturated aqueous sodium chloride solution and then dried over sodium sulfate. After concentration under vacuum, the residual white powder was recrystallized with ethyl acetate-hexane solution to yield 0.64 g 3-(cyanopentyl)-7-methylxanthine (15% yield) as a white solid.

Workup

  1. customThe mixture was then quenched with 150 mL water
  2. extractionextracted five times with 35 ml methyl acetate
  3. washThe combined extracts were washed two times with 40 ml saturated aqueous sodium bicarbonate solution and two times with 40 ml saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationAfter concentration under vacuum
  6. customthe residual white powder was recrystallized with ethyl acetate-hexane solution

Sources & evidence

ORD record
ord-f742a5c71eac4eac9ed962676c044553
Source dataset
uspto-grants-2002_10
Patent number
US06469017B1

Linked notes

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