Sodium Hydroxide → 2-Amino-5-methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin

Participants

Reaction Conditions

Reaction Steps

Crude N-[1-(3-amino-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)ethyl]-3-(trifluoromethyl)benzamide (Intermediate 42) (8.34 g, 25.5 mmol) was suspended in POCl3 (30 mL) and heated in a sealed tube at 110° C. for 2h. After the reaction had cooled to rt, the solution was carefully poured onto ice, neutralized with NaOH(aq) and extracted into EtOAc. The combined organic extracts were dried (MgSO4), filtered, and concentrated. Purification of the residue by chromatography afforded 2-amino-5-methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-4(3H-one (1.63 g) as a pale yellow solid. 1H NMR (DMSO-d6): δ10.91 (s, 1H), 8.75-8.71 (m, 1H), 8.66 (s, 1H), 7.77-7.68 (m, 2H), 6.25 (bs, 2H), 2.48 (s, 3H). MS m/z 308 (M−1).

Provenance & Evidence