Hydrochloric Acid → HCID 86690742, compound

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To a mixture of 3-((tert-butyldimethylsilyloxy)methyl)-2-(1-methyl-1H-pyrazol-5-yl)pyridine and 3-((tert-butyldimethylsilyloxy)methyl)-2-(1-methyl-1H-pyrazol-3-yl)pyridine (420 mg, 1.38 mmol) in MeOH (20 mL) was added HCl (4 N, 2.0 mL). The mixture was stirred at rt for 1 h, concentrated, and diluted with EtOAc (50 mL) and NaHCO3(sat) solution (10 mL). The layers were separated and aqueous layer was extracted with EtOAc three times. The combined organic layers were dried over Na2SO4, concentrated, and purified on silica gel using EtOAc as eluent to give (2-(1-methyl-1H-pyrazol-5-yl)pyridin-3-yl)methanol (187 mg, 72%) and (2-(1-methyl-1H-pyrazol-3-yl)pyridin-5-yl)methanol (55 mg, 21%) as white solids. Data for 2-(1-methyl-1H-pyrazol-5-yl)pyridin-3-yl)methanol: 1H NMR (400 MHz; CDCl3) 8.58 (d, 1H), 7.91 (d, 1H), 7.46 (s, 1H), 7.30 (dd, 1H), 6.36 (s, 1H), 4.62 (d, 2H), 3.83 (s, 3H), 2.1 (t, 1H). LRMS (M+H+) m/z 190.1; data for (2-(1-methyl-1H-pyrazol-3-yl)pyridin-5-yl)methanol: 1H NMR (400 MHz; CDCl3) 8.60 (d, 1H), 7.70 (d, 1H), 7.47 (s, 1H), 7.22 (dd, 1H), 6.99 (s, 1H), 5.91 (t, 1H), 4.68 (d, 2H), 4.01 (s, 3H). LRMS (M+H+) m/z 190.1

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