Tetrahydrofuran → HCID 23153217, compound

Participants

Reaction Steps

To a solution of 6-(2-fluoro-4-nitrophenoxy)pyrimidin-4-ylamine (250 mg) in tetrahydrofuran (10 ml) were added triethylamine (0.307 ml) and phenyl chloroformate (0.264 ml) in this order, followed by stirring at room temperature for 30 min. The reaction mixture was concentrated to give a residue. To the residue was added N,N-dimethylformamide (5.0 ml), methyl-[1-(1-methylazetidin-3-yl)piperidin-4-yl]amine (1.07 g), followed by stirring at room temperature for 36 hrs. The reaction mixture was partitioned between ethyl acetate and an 1N aqueous solution of sodium hydroxide. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated to give a residue, which was then purified by silica gel column chromatography (FUJI Silysia NH, eluent; ethyl acetate, then ethyl acetate:methanol=20:1). Fractions containing a target compound were concentrated to give a powder, which was suspended hexane (5 ml). It was filtered off, dried under aeration to provide the titled compound (193 mg, 42.0%) as yellow powder.

Provenance & Evidence