2-METHYLSULFANYL-PYRIMIDINE-4-CARBALDEHYDE

180869-36-7

1074-68-6

Example 4 Synthesis of 2-(methylthio)pyrimidine-4-carboxaldehyde (4): 4-(dimethoxymethyl)-2-(methylthio)pyrimidine (3) (53.7 g, 268 mmol) was slowly added to an aqueous solution of 1.2N HCl (300 mL, 268 mmol, 1.0 eq.) at 60 °C with continuous stirring for 3 hours. Upon completion of the reaction, the mixture was cooled to room temperature and neutralized by slow addition of solid sodium bicarbonate. Subsequently, the crude product was extracted with ether (3 x 150 mL) and the combined organic layers were concentrated under reduced pressure to afford the target product 2-(methylthio)pyrimidine-4-carboxaldehyde (4) as a yellow solid (14.2 g, 34% yield).LC-MS m/z 155 (M+1). Reference: WO 2006/009734 A1, p. 67.