Hydrazine → 7-Pyrimidin-5-yl-1-benzofuran-5-amine

Participants

Reaction Steps

Raney-nickel (slurry in ethanol; 2 mL) and hydrazine (0.378 g, 7.55 mmol) were added to 5-(5-nitro-1-benzofuran-7-yl)pyrimidine (0.455 g, 1.87 mmol, Intermediate 17) in ethanol/THF (100 mL:25 mL). The mixture was stirred at room temperature for 3 h, filtered through Celite and concentrated in vacuo to afford 0.317 g (80%) of the title compound as a yellow solid. HPLC 100%, RT: 0.957 min (System A; 10-97% over 3 min). 1H NMR (270 MHz, methanol-d4) δ ppm 6.77 (d, J=2.23 Hz, 1H) 7.05 (q, J=2.23 Hz, 2H) 7.76 (d, J=2.23 Hz, 1H) 9.14 (s, 1H) 9.26 (s, 2H). LC-MS 212 (M+H)+.

Provenance & Evidence