Tert-butyl {4-chloro-2-fluoro-5-[(5-nitro-4-thiocyanatopyrimidin-2-yl)amino]phenyl}carbamate → Tert-butyl {5-[(2-amino[1,3]thiazolo[5,4-d]pyrimidin-5-yl)amino]-4-chloro-2-fluorophenyl}carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of the above-mentioned crude product of tert-butyl {4-chloro-2-fluoro-5-[(5-nitro-4-thiocyanatopyrimidin-2-yl)amino]phenyl}carbamate in acetic acid (20 mL) was added reduced iron (697 mg, 12.5 mmol), and the mixture was stirred at 80° C. for 30 min. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. To the obtained residue was added saturated aqueous sodium hydrogen carbonate solution (50 mL), and the mixture was extracted with ethyl acetate/tetrahydrofuran mixture (1:1, 50 mL, 20 mL). The combined organic layer was washed with saturated brine (10 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was washed with ethyl acetate to give the title compound (487 mg, 6%) as a pale-yellow solid.

Provenance & Evidence