HCID 57758046, compound → Ethyl 4-amino-5-(4-aminophenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate

Participants

Reaction Steps

Raney nickel was added to a flask containing ethanol (20 mL). The catalyst was triturated with ethanol (3×20 mL) and the a suspension of ethyl 4-amino-5-(4-nitrophenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate (4.0 g, 12.2 mmol) in ethanol (600 mL) and THF (200 mL) was added. The reaction was then placed under a hydrogen atmosphere (1 atm) and allowed to stir at rt overnight. The reaction was filtered through a pad of Celite® using a mixture of ethanol and THF (3:1) to rinse. The filtrate was concentrated in vacuo to afford the desired product (3.60 g, 96%). 1H-NMR (DMSO-d6) 8.05 (s, 1H), 8.04 (br s, 2H), 7.88 (s, 1H), 7.01 (d, J=8.0 Hz, 2H), 6.61 (d, J=8.0 Hz, 2H), 5.31 (br s, 2H), 4.07 (q, J=7.3 Hz, 2H), 1.12 (t, J=7.3 Hz, 3H); ES-MS m/z 298.2 (MH)+; HPLC RT (Method A) 1.64 min; TLC Rf=0.30 (Acetone/CH2Cl2 1:3).

Provenance & Evidence