Potassium Cyanide → HCID 20773487, compound

HRID 1814966Notes

Reaction equation

CS(O[C@@H:6]([CH3:32])[CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:20](=[O:21])[C:19]2[NH:18][C:17]([CH2:22][NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[N:16][C:15]=2[N:14]([CH3:31])[C:12]1=[O:13])(=O)=O.[C-:33]#[N:34].[K+]>CS(C)=O>[C:33]([C@H:6]([CH3:32])[CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:20](=[O:21])[C:19]2[NH:18][C:17]([CH2:22][NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[N:16][C:15]=2[N:14]([CH3:31])[C:12]1=[O:13])#[N:34]

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of (S)-1-(5-methanesulfonyloxyhexyl)-8-(N-BOC-aminomethyl)-3-methylxanthine (0.47 g, 1.0 mmol) and potassium cyanide (0.39 g, 6.0 mmol) in dimethylsulfoxide (8.0 ml) was stirred at 60° C. overnight. The reaction was quenched by addition of water (30 ml) and extracted with ethyl acetate (3×15 ml). The combined extracts were washed with water (2×15 ml), saturated aqueous sodium chloride solution (15 ml), dried over magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with 15% methanol-ethyl acetate to give (R)-1-(5-cyanohexyl)-8-(N-BOC-aminomethyl)-3-methylxanthine (0.25 g, 62% yield) as an oil.

Workup

customThe reaction was quenched by addition of water (30 ml)
extractionextracted with ethyl acetate (3×15 ml)
washThe combined extracts were washed with water (2×15 ml), saturated aqueous sodium chloride solution (15 ml)
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe crude product was purified by flash chromatography on silica gel eluting with 15% methanol-ethyl acetate

Sources & evidence

ORD record: ord-43e3513af7ab423f96bf8a182c89ee65
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06878715B1

Reaction notes

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