3-Methyl-2-butanone → HCID 66743775, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-amino-5-(pyridin-4-yl)thiophene-2-carboxamide (0.108 g, 0.500 mmol), 3-methyl-2-butanone (3.0 mL), p-toluenesulfonic acid monohydrate (0.0095 g, 0.050 mmol) and acetic acid (3.0 mL) was stirred overnight at 70° C. in a sealed tube. The mixture was poured into sat. aqueous sodium hydrogen carbonate (150 mL). Extraction with ethyl acetate-tetrahydrofuran (3:1, 2×100 mL), drying over magnesium sulfate, filtration and concentration at reduced pressure gave a solid. This solid was dissolved with DMF-dichloromethane (2:5, 7 mL) and purified by column chromatography (Combiflash, 12 g silica gel, ethyl acetate to 90:10 ethyl acetate/methanol), then recrystallized from methanol-ethyl acetate to afford the title compound (0.0125 g, 8.7%) as a yellow solid:

Provenance & Evidence