Methyltriphenylphosphonium iodide → 4-(4-Benzyl-phthalazin-1-yl)-5'-isopropenyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

Methyltriphenylphosphonium iodide (115 mg, 0.28 mmol) is dissolved in THF (750 μL) and chilled to 5° C. While stirring add potassium t-butoxide (310 μL, 1M in THF, 0.31 mmol) to the solution. After 30 minutes add the mixture to a solution of 1-[4-(4-Benzyl-phthalazin-1-yl)-3,4,5,6-tetrahydro-2H-[1,2]bipyrazinyl-5′-yl]-ethanone (100 mg, 0.24 mmol) and THF (750 μL). Stir 30 minutes. Analysis shows 60-70% completion. A second portion of methyl triphenyl phosphonium iodide (115 mg, 0.28 mmol) is dissolved in THF (750 μl) and chilled to 5° C. While stirring add potassium t-butoxide (310 μL, 1M in THF, 0.31 mmol) to the solution. Again add this mixture to the current reaction. Reaction quickly proceeds to completion. Quench by adding saturated ammonium chloride. Concentrate in vacuo to remove THF and partition between water and EtOAc. Extract with EtOAc, and wash combined organics with brine. Concentrate EtOAc in vacuo. The residue is purified by flash chromatography on silica gel (EtOAc/Heptane) to afford the title compound (80 mg, 78%).

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