HCID 12318256, compound → ethyl 4-amino-1-methyl-1H-imidazole-5-carboxylate

Participants

Reaction Steps

Ethyl 4-amino-1-methyl-2-(methylthio)imidazole-5-carboxylate (1.52 g, 7.11 mmol) and W-2 Raney nickel (3 g, 50% in water) in ethanol (25 mL) were heated at reflux for 12 hours. Additional Raney nickel (ca 1.5 g, 50% in water) was added and heating was continued for an additional 3 hours adding Raney nickel (ca 1.5 g, 50% in water) every hour. The reaction was filtered and the filtrate evaporated under reduced pressure. Chromatography of the residue on silica gel eluting with 1.5% methanol in chloroform afforded 0.72 g (60%) of the desired product as a solid. TLC (10% methanol/90% chloroform) Rf =0.47. 1H NMR (CDCl3, 300 MHz) d 1.38 (t, 3H), 3.77 (s, 3H), 4.32 (q, 2H), 4.82 (br, 2H), 7.13 (s, 1H). MS (DCl/NH3) m/e 170 (M+H)+ .

Provenance & Evidence