NaH (0.223 g, 5.5 mmol) was washed with heptane (10 ml), then suspended in DMF (5 ml). N-(Tetrahydro-2H-pyran-2-yloxy) 2-{6-[(naphthalene-2-sulfonyl)amino]-3-azabicyclo[3.1.0]hex-3-yl}pyrimidine-5-carboxamide (0.991 g, 1.95 mmol) was added, and the mixture stirred for 5 min. To NaH (0.172 g, 4.3 mmol) in DMF was added 1-(2-chloroethyl)-pyrrolidine hydrochloride (0.724 g, 4.2 mmol). The reaction was swirled gently for 2 min, and then added to the solution of N-(tetrahydro-2H-pyran-2-yloxy) 2-{6-[(naphthalene-2-sulfonyl)amino]-3-azabicyclo[3.1.0]hex-3-yl}pyrimidine-5-carboxamide. The mixture was stirred at r.t. for 5 days, then poured into DCM (150 ml) and quenched with 2.4M ammonium chloride solution (50 ml). The organic layer was separated, and the aqueous was further extracted with DCM (150 ml). The combined organic extracts were dried, concentrated in vacuo to give the title compound (0.234 g, 19%). This was carried forward without further purification.
