2-Fluoro-4-nitrophenol → 4-Amino-6-(2-fluoro-4-nitrophenoxy)pyrimidine

Participants

Reaction Conditions

Reaction Steps

2-Fluoro-4-nitrophenol (1.736 g) was dissolved in dimethyl sulfoxide (10 ml), and then sodium hydride (400 mg) was added thereto, followed by stirring for 20 min. Then, 4-amino-6-chloropyrimidine (648 mg) was added thereto, followed by stirring at 100° C. for 45 min. The reaction mixture was heated up to 120° C., followed by stirring for 1 hr and 25 min. Then, the reaction mixture was heated up to 140° C., followed by stirring overnight. The reaction mixture was cooled down to room temperature, and then a 1 N aqueous solution of sodium hydroxide (10 ml) was added thereto, followed by stirring and extracting with ethyl acetate. The organic layer was washed with a 1 N aqueous solution of sodium hydroxide, water and brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure to give a residue, which was then purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:2). The solvent was evaporated under a reduced pressure to give a residue, which was suspended in diethyl ether (7 ml)-hexane (3.5 ml). The solid was filtered off, and dried under aeration to provide the titled compound (201 mg, 16.0%) as pale brown powder.

Provenance & Evidence