Methyl acetoacetate → HCID 22477278, compound

Participants

Reaction Conditions

Reaction Steps

A solution of methyl acetoacetate (1.35 mL) in N-methylpyrrolidone (15 mL), cooled to 0° C., was treated portionwise with sodium hydride (0.33 g, 60% dispersion in mineral oil) and after stirring at 0° C. for 30 minutes this mixture was then treated with a solution of [6-(4-tert-butylphenyl-5H-pyrrolo[2,3-b]pyrazin-7-yl]methyltrimethylammonium iodide [2 g, Reference Example 45(a)] in N-methylpyrrolidone (100 mL). After stirring at room temperature overnight the reaction mixture was subjected to chromatography on silica eluting with a mixture of heptane and ethyl acetate. The resulting 2-acetyl-[6-(4-tert-butyl-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]propionic acid, methyl ester (1.2 g) was dissolved in a mixture of sodium hydroxide (250 mL, 2N), methanol (25 mL) and tetrahydrofuran. This solution was then heated at 50° C. for 1 hour, then evaporated, then acidified by addition of hydrochloric acid (25 mL, 2N) and then extracted with ethyl acetate. The organic extract was dried over sodium sulfate and then evaporated to give the title compound (1 g). MS: 322 (MH+).

Provenance & Evidence