Triethylamine → 3-(6-chloro-1-ethyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane

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To a cloudy solution of 2,4,6-trichloro-pyrimidine-5-carbaldehyde (1.1 g, 5.2 mmol) in chloroform (50 mL) cooled to −78° C. was added ethylhydrazine oxalate (0.78 g, 5.2 mmol) in two portions, followed by triethylamine (2.7 mL). The cooling bath was then removed and ethanol (10 mL) was added to the reaction mixture, which was allowed to warm to room temperature. 8-Oxa-3-azabicyclo[3.2.1]octane hydrochloride (0.69 g, 4.6 mmol) was added to the mixture. The mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate and water. The aqueous phase was extracted three times with ethyl acetate. The combined organics were washed successively with 5% aqueous potassium hydrogen sulfate solution, water, saturated aqueous sodium hydrogen carbonate solution, and saturated aqueous sodium chloride solution. Organics were dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to provide 3-(6-chloro-1-ethyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane. MS (ES+): 293.9, 295.9 (M+H)+

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