Methyl iodide → 6-Chloro-1,4-dimethyl-3-oxo-1,3-dihydro-pyrazolo[3,4-b]pyridine-2-carboxylic acid 2-methylbenzylamide

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Reaction Conditions

Reaction Steps

99.89 mg (0.3 mmol) of 6-chloro-4-methyl-3-oxo-1,3-dihydropyrazolo[3,4-b]pyridine-2-carboxylic acid 2-methylbenzylamide and 37.3 mg (0.33 mmol) of potassium tert-butoxide were stirred in 10 ml of THF at room temperature for 10 minutes. Addition of 20.7 μl of iodomethane was followed by stirring at room temperature for 2 h and at 60° C. for 4 h. Then 30 μl of iodomethane and 50 μl of triethylamine were added, and stirring was continued at 60° C. for 7 h, the mixture was concentrated and mixed with water and ethyl acetate, and the organic phase was separated off, concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 18 mg (17%), M+H+: 345.08.

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