Synthesis
Ethyl 4,6-dimethylpyrimidine-5-carboxylate (10.9 g, 0.0605 mol) was used as starting material, which was mixed with an aqueous solution (70 mL) of sodium hydroxide (4.0 g, 0.10 mol). The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the reaction solution was acidified with concentrated hydrochloric acid and subsequently the solution was concentrated to dryness. To the dried residue, acetone (100 mL) was added, the insoluble sodium chloride was removed by filtration, and the solid was washed with methanol (100 mL). The filtrate was concentrated to dryness and the resulting residue was washed with acetonitrile (ACN) to give a final 8.5 g (92% yield) of 4,6-dimethylpyrimidine-5-carboxylic acid solid product. The mass spectrum (EI) showed a m/z of 153.1 (M + 1). 1H NMR (400 MHz, CD3OD) data were as follows: δ 8.89 (s, 1H), 2.56 (s, 6H).
References
[1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 4, p. 709 - 712
[2] Patent: US2005/261310, 2005, A1. Location in patent: Page/Page column 1220
[3] Patent: US6391865, 2002, B1. Location in patent: Page column 86
[4] Patent: EP1175402, 2005, B1. Location in patent: Page/Page column 54
[5] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 3, p. 567 - 571
