Synthesis
2-Methyl-5-pyrimidinecarboxaldehyde (8 g, 66 mmol, compound 44b) was dissolved in methanol (100 mL) at 0°C and sodium borohydride (7.5 g, 197 mmol) was slowly added. The reaction temperature was maintained in the range of 0-15°C and the reaction mixture was stirred for 3 hours. Upon completion of the reaction, the reaction was quenched with saturated ammonium chloride solution (30 mL) and subsequently extracted with ethyl acetate (20 mL x 3). The organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification of the residue by silica gel column chromatography afforded (2-methylpyrimidin-5-yl)methanol (4.1 g, 51% yield, compound 44c) as a white solid.
References
[1] Patent: WO2016/180695, 2016, A1. Location in patent: Page/Page column 153
[2] Patent: US2014/107340, 2014, A1. Location in patent: Paragraph 0121
[3] Patent: US2008/275037, 2008, A1. Location in patent: Page/Page column 29
[4] Patent: WO2010/33168, 2010, A2. Location in patent: Page/Page column 80-81
