1H-1,2,4-Triazole → 7-(5-bromopyridin-3-yl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine

In a similar manner as described for Example 9, 5-bromo-N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)nicotinamide (Intermediate 20) (0.15 g, 0.31 mmol) and 1,2,4-triazole (128 mg, 1.9 mmol) in pyridine (4 mL) and phosphorus oxychloride (0.087 mL, 0.93 mmol) gave 7-(5-bromopyridin-3-yl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine (0.011 g) as a yellow solid. 1H NMR (Acetone-d6): δ9.81-9.78 (m, 1H), 9.18 (s, 1H), 8.93-8.90 (m, 1H), 8.73-8.70 (m, 1H), 8.57 (s, 1H) 7.12 (s, 2H), 3.73 (s, 3H), 3.73 (s, 3H), 3.70 (s, 3H), 2.59 (s, 3H). MS m/z 471, 473 (M+1, M+3).