Hydrazine → HCID 66664953, compound

Participants

Reaction Steps

To a solution of tert-butyl 4-(2-(3-nitrophenyl)-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate (769 mg, 1.677 mmol) in EtOH (12 ml) at room temperature is added Raney® 2400 nickel (98 mg, 1.677 mmol) followed by hydrazine (0.526 ml, 16.77 mmol) dropwise and the mixture is stirred at room temperature for 4 hours. The reaction is monitored by TLC and LMCMS and additional nickel and hydrazine is added until completion. The mixture is filtered over celite and concentrated in vacuo to give crude tert-butyl 4-(2-(3-aminophenyl)-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate (443 mg, 1.034 mmol, 61.6% yield) as a tan solid.

Provenance & Evidence