Methanol → N-(3-(1H-pyrazolo[3,4-d]pyrimidin-4-yl)pyridin-2-yl)-1-chloro-6-methylisoquinolin-5-amine

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A mixture of 1-chloro-6-methylisoquinolin-5-amine (414 mg, 2147 μmol) and 4-(2-fluoropyridin-3-yl)-1H-pyrazolo[3,4-d]pyrimidine (420 mg, 1952 μmol) in THF (20 ml) was sonicated until all solid became a fine powder. Lithium bis(trimethylsilyl)amide, 1.0 M solution in THF (6831 μl, 6831 mmol) was then added (all solids were dissolved and color changed) The mixture was stirred at rt overnight. The mixture was poured into a mixture of MeOH (20 ml) and AcOH (2 ml) and then solvent was removed in vacuo. 2 M NH3/MeOH (30 ml) was added and then solvent was removed in vacuo. The product was purified by flash chromatography eluting with MeOH/DCM (0-5%) to give N-(3-(1H-pyrazolo[3,4-d]pyrimidin-4-yl)pyridin-2-yl)-1-chloro-6-methylisoquinolin-5-amine. MS Found (ESI pos. ion) m/z 388 (M+H+).

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