Hydrochloric Acid → 2-methoxy-5-((2-(4-methyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)isonicotinaldehyde

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Reaction Steps

To 2-methoxy-5-((2-(4-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)isonicotinaldehyde (110 mg, 0.27 mmol, 1 equiv) suspended in EtOH (1 mL) was added HCl (1.0 mL, 3 N). The solution turned homogeneous and the mixture was stirred at rt overnight. The EtOH was partially removed by blowing in N2 gas and basified to pH 9. The aqueous solution was extracted with EtOAc three times. The organic layer was dried over Na2SO4 and concentrated. The crude was purified on silica gel using a mixture of MeOH and DCM as eluent to give 2-methoxy-5-((2-(4-methyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)isonicotinaldehyde (40 mg, 46%) as a white solid. 1H NMR (400 MHz; CDCl3) δ=10.45 (s, 1H), 8.76 (d, 1H), 8.07 (br, 1H), 8.05 (s, 1H), 7.53 (s, 1H), 7.40 (dd, 1H), 7.13 (s, 1H), 5.52 (br, 2H), 3.98 (s, 3H). LRMS (MAT) m/z 325.1.

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