Ethanol → tert-butyl 4-((6-fluoro-5-(2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-3-yl)methyl)piperazine-1-carboxylate

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A mixture of 5-((4-(tert-butoxycarbonyl)piperazin-1-yl)methyl)-2-fluoropyridin-3-ylboronic acid (655 mg, 1.931 mmol), 6-chloro-2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (586 mg, 2.317 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (Aldrich) (25.6 mg, 0.097 mmol) and potassium acetate (285 mg, 4.83 mmol) in ethanol (6.00 mL, 103 mmol) and H2O (1.00 mL, 55.5 mmol) was heated at 80° C. for 2 h. After cooling, the reaction mixture was concentrated and the crude product was adsorbed onto a plug of silica gel and chromatographed through a RediSep®, Teledyne ISCO, Lincoln, Nebr., pre-packed silica gel column (pure hexanes to 50% ethyl acetate in hexane) to give the tert-butyl 4-((6-fluoro-5-(2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-3-yl)methyl)piperazine-1-carboxylate as a pale yellow foam (0.877 g, 89%). LCMS (API-ES) m/z 512 (M+H)+.

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