Acetonitrile → N-(3-(5-(2-aminopyrimidin-5-yl)-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)phenyl)acetamide

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Reaction Steps

4-(5-Chloro-2-iodothiazolo[4,5-d]pyrimidin-7-yl)morpholine 27, 3-acetamido-phenyl boronic acid (1.2 eq), and trans-dichlorobis(triphenylphosphine)palladium(II) (0.1 eq) were slurried with equal parts 1M sodium carbonate aqueous solution (3 eq) and acetonitrile. The solution was microwaved at 90° C. for 10 minutes. Water was added and the solution was filtered. The aqueous layer was dried and combined with 5-pyrimidine-2-amine boronic acid (1.2 eq) and trans-dichlorobis(triphenylphosphine)palladium(II) (0.1 eq) and slurried with equal parts 1M sodium carbonate aqueous solution (3 eq) and acetonitrile. The solution was microwaved at 150° C. for 10 minutes. Water was added and the solution was filtered. The resulting precipitate was purified by reverse phase silica gel chromatography to yield 140.

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