N-methylthiophen-3-amine → (2-morpholin-4-yl-ethyl)-[3-{6-[(thiophen-3-ylmethyl)-amino]-pyridin-2-yl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-amine

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A sealed tube was charged with [3-(6-bromo-pyridin-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-(2-morpholin-4-yl-ethyl)-amine (from Example 32 supra) (320 mg, 0.60 mmol), thiophen-3-yl-methylamine (81 mg, 0.72 mmol), Pd2(dba)3 (34 mg), DavePhos (47 mg), t-BuONa (69 mg, 0.72 mmol) and dioxane (12 mL). The mixture was stirred at 105° C. under an atmosphere of N2 for 8 hours. After cooling to room temperature, the mixture was filtered and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 16 g, 100-200 mesh, eluting with MeOH:dichloromethane, 1:100 to 1:80) to give crude (2-morpholin-4-yl-ethyl)-[3-{6-[(thiophen-3-ylmethyl)-amino]-pyridin-2-yl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-amine as a yellow oil. (Yield 149 mg).

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