Cesium carbonate → 2-(1-(2-(9-methyl-2-(2-methyl-1H-benzo[d]imidazol-1-yl)-6-morpholino-9H-purin-8-yl)ethyl)piperidin-4-yl)propan-2-ol

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A mixture of 2-{1-[2-(2-chloro-9-methyl-6-morpholin-4-yl-9H-purin-8-yl)ethyl]-piperidin-4-yl}propan-2-ol (47 mg, 0.11 mmol), 2-methylbenzimidazole (16 mg, 0.12 mmol), Pd2(dba)3 (2.5 mg, 2.5 mol %), Xphos (5.0 mg, 10 mol %) and Cs2CO3 (54 mg, 0.17 mmol) in dioxane (1.0 mL) was purged with argon gas then heated at 150° C., for 30 min, in a microwave reactor. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge, washed with MeOH then the desired product eluted with 2 M NH3 in MeOH. The resulting residue was purified by flash chromatography (RediSep amine cartridge, 0-5% MeOH in DCM) followed by reverse phase HPLC (Phenomenex Gemini 5 μm C18, 20 mM triethylamine in water on a gradient of acetonitrile 30-50%) to give 344 (25 mg, 43%) as a white solid. LCMS: (Method G): RT 5.64 min; [M+H]+ 519.3. 1H NMR (400 MHz, CHCl3-d): δ 8.09-8.04 (m, 1 H), 7.73-7.69 (m, 1 H), 7.29-7.24 (m, 2 H), 4.48-4.16 (m, 4 H), 3.87 (t, J=4.7 Hz, 4 H), 3.79 (s, 3 H), 3.23-1.05 (m, 4 H), 2.93 (s, 3 H), 2.93-2.75 (m, 2 H), 2.11 (s, 3 H), 1.90-1.75 (m, 2 H), 1.55-1.25 (m, 3 H), 1.20 (s, 6 H)

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