Aniline → HCID 11438062, compound

Participants

Reaction Steps

A solution of aniline (18 mg, 0.19 mmol) in tetrahydrofuran (5 mL) at −78° C. was treated with n-butyllithium (0.13 mL of a 1.6M solution in hexanes, 0.21 mmol) and the resulting mixture stirred at this temperature for 0.5 h. The mixture was then treated with a solution of of 5-methyl-2-(methylthio)-7-phenylimidazo[5,1-f][1,2,4]triazine (Intermediate 72) (50 mg, 0.17 mmol) in tetrahydrofuran (5 mL) and the mixture allowed to warm slowly to room temperature overnight. The mixture was then reduced under vacuum and partitioned between ethyl acetate and saturated aqueous sodium bicarbonate and the layers separated. The organic layer was then dried with magnesium sulfate, filtered and reduced. The crude product was purified by chromatography on silica gel eluting with 50% ethyl acetate in petrol to afford 5-methyl-N,7-diphenylimidazo[5,1-f][1,2,4]triazin-2-amine (10 mg) as a yellow solid. MS m/z 302 (M+1).

Provenance & Evidence