Methanol → 2-Furan-2-yl-6-(3-phenyl-3-phenylamino-prop-1-ynyl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine

Participants

Reaction Conditions

Reaction Steps

To a solution of benzylidene-phenyl-amine (0.05 mmol) (prepared by heating neat phenylamine (0.05 mmol) and benzaldehyde (0.05 mmol) at 60° C. for 2 hours) in a 1:1 mixture of THF (250 uL) and methanol (250 uL) was added the above 6-ethynyl-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine (11 mg, 0.05 mmol). CuBr (2.2 mg, 0.015 mmol, 30 mol %) was added to the reaction mixture followed by RuCl3 (0.03 mg, 0.0015, 3 mol %) in water (50 μL). The reaction vessel was degassed and heated at 40° C., for 18 hours. After cooling, water was added and the residue was extracted with ethyl acetate. The combined organic extracts were dried over magnesium sulfate, and concentrated in vacuo to yield a crude product, which was purified using preparative HPLC to afford 2-furan-2-yl-6-(3-phenyl-3-phenylamino-prop-1-ynyl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine. 1H NMR (300 MHz, Acetone-d6) δ 8.20 (s, 1H), 7.79-7.71 (3H), 7.43-7.40(3H), 7.15-7.11(4H), 6.90-6.87(2H), 6.67-6.65 (2H), 5.70 (s, 1H), 2.55(s, 1H). MS: m/z 407 [M+1].

Provenance & Evidence