Uses
5-Hydroxypyrazine-2-carboxylic Acid Methyl Ester is a metabolite of Pyrazinamide (P840600), an antibacterial (tuberculostatic).
Synthesis
General procedure for the synthesis of methyl 5-hydroxypyrazine-2-carboxylate from methanol and 5-oxo-4,5-dihydropyrazine-2-carboxylic acid: Acetyl chloride (152 mL, 2.08 mol) was slowly added dropwise to methanol (5 L) at -20 °C. After the dropwise addition was completed, stirring was continued at this temperature for 30 minutes. Subsequently, 5-hydroxypyrazine-2-carboxylic acid (100 g, 714 mmol) was added and the mixture was heated to reflux and the reaction was maintained for 2 hours. Upon completion of the reaction, the solvent was removed by vacuum concentration and the residue was recrystallized from methanol (400 mL) to give 71 g (464 mmol) of methyl 5-hydroxypyrazine-2-carboxylate in 65% yield.
References
[1] Patent: WO2013/14567, 2013, A1. Location in patent: Page/Page column 80-81
[2] Patent: EP2239253, 2010, A1. Location in patent: Page/Page column 96
[3] Patent: EP1452525, 2004, A1. Location in patent: Page 15
