Citric Acid → 3-Amino-6-iodo-pyrazine-2-carboxylic acid dimethylamide

참여 물질

반응 단계

534 mg (2.02 mmol) of 3-amino-6-iodo-pyrazine-2-carboxylic acid were dissolved in 20 mL of 50% v/v acetonitrile in dichloromethane containing 350 μL (2.01 mmol) of di-iso-propyl-ethylamine. 818 mg (2.18 mmol) of N,N,N′,N′,-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate were added. Upon stirring for 3 minutes at ambient temperature 2.5 mL (5 mmol) of 2.0 M dimethylamine in anhydrous THF was added and stirring was continued for 23 h. The resulting solution was distributed between dichloromethane and 10% w/v aqueous citric acid solution. The organic phase was dried over sodium sulfate and evaporated. The resulting crude was purified by flash chromatography on silica gel using a gradient of ethyl acetate and hexanes to afford 363 mg (1.24 mmol, 62%) of 3-amino-6-iodo-pyrazine-2-carboxylic acid dimethylamide as a pale yellow crystalline solid. 1H-NMR [500 MHz, d6-DMSO] δ: 8.25 (s, 1H), 6.71 (s, hr., 2H), 2.98 (s, 3H), 2.92 (s, 3H); MS [MH+] m/z: 293.

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