Water → N-ethoxy-1-methyl-2,2-dioxo-6-[1-(3-pyridyl)pyrazol-4-yl]pyrido[3,2-c]thiazin-4-imine

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To Na2CO3 (183 mg, 1.71 mmol) was added water (1.5 ml) and acetonitrile (2 ml) and the solution was degassed for 5 min with argon. 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazol-1-yl]pyridine (111 mg, 0.41 mmol), 6-bromo-N-ethoxy-1-methyl-2,2-dioxo-pyrido[3,2-c]thiazin-4-imine (114 mg, 0.34 mmol) and Pd(dppf)Cl2 (25 mg, 0.034 mmol) were added sequentially followed by rinsing the flask with acetonitrile (2 ml). The mixture was stirred at 80° C. for 1.5 h followed by cooling to ambient temperature. Water and ethyl acetate were added then the phases were separated. The aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography eluting with ethyl acetate/heptane, gradient, afforded N-ethoxy-1-methyl-2,2-dioxo-6-[1-(3-pyridyl)pyrazol-4-yl]pyrido[3,2-c]thiazin-4-imine as a red solid as a single isomer.

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