Isopropyl methanesulfonate → 6-[5-(3-Isopropoxyazetidin-1-yl)-[1,2,4]oxadiazol-3-yl]-N-methyl-N-phenyl-[1,3,5]triazine-2,4-diamine

関与物質

反応手順

Sodium hydride (60% dispersion in mineral oil, 9 mg, 0.22 mmol) was added to a solution of 1-{3-[4-amino-6-(methyl-phenyl-amino)-[1,3,5]triazin-2-yl]-[1,2,4]oxadiazol-5-yl}-azetidin-3-ol (Intermediate 166, 50 mg, 0.147 mol) in anhydrous DMF (0.5 mL) at 0 C under nitrogen and the mixture was stirred for 10 min. A solution of propan-2-yl methanesulfonate (26.7 μL, 0.221 mmol) in anhydrous DMF (0.5 mL) was then added and the mixture was stirred at room temperature for 18 h. Further sodium hydride (60% dispersion in mineral oil, 9 mg, 0.22 mmol) and propan-2-yl methanesulfonate (26.7 μL, 0.221 mmol) were then added and the mixture was stirred at room temperature for 4 h. The mixture was diluted with EtOAc (10 mL) then washed with saturated aq. sodium carbonate (4×5 mL), brine (5 mL) and evaporated under vacuum. The crude residue was purified by flash chromatography (0-2% (7M ammonia in MeOH) in DCM) to afford the title compound as a light yellow glass (22 mg, 39%).

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