Potassium Cyanide → (R)-1-(5-acetoxyhexyl)-7-benzyl-8-cyano-3-methylxanthine

HRID 1355397Notes

Reaction equation

[C:1]([O:4][C@H:5]([CH3:30])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16](Br)=[N:15][C:14]=2[N:13]([CH3:29])[C:11]1=[O:12])(=[O:3])[CH3:2].[C-:31]#[N:32].[K+]>CS(C)=O>[C:1]([O:4][C@H:5]([CH3:30])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]([C:31]#[N:32])=[N:15][C:14]=2[N:13]([CH3:29])[C:11]1=[O:12])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of (R)-1-(5-acetoxyhexyl)-7-benzyl-8-bromo-3-methylxanthine (9.55 g, 20.0 mmol) in anhydrous dimethylsulfoxide was added potassium cyanide (1.43 g, 22.0 mmol). After stirring at 70-80° C. for 4.5 hours, the mixture was cooled to room temperature, quenched with water (500 ml) and extracted with ethyl acetate (4×150 ml). The combined extracts were washed with saturated aqueous sodium chloride solution (45 ml), dried over magnesium sulfate and the solvent was evaporated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:1) to provide (R)-1-(5-acetoxyhexyl)-7-benzyl-8-cyano-3-methylxanthine (7.60 g, 90% yield) as a beige powder.

Workup

temperaturethe mixture was cooled to room temperature
customquenched with water (500 ml)
extractionextracted with ethyl acetate (4×150 ml)
washThe combined extracts were washed with saturated aqueous sodium chloride solution (45 ml)
dry with materialdried over magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe crude product was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:1)

Sources & evidence

ORD record: ord-dd900634b1444fc4913e735fa2e85286
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586429B2

Reaction notes

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