[CH:1]([N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11]2[S:15][C:14]([CH:16]=[O:17])=[CH:13][CH:12]=2)=[CH:5]1)([CH3:3])[CH3:2].[CH3:18][Mg]Br.C(OCC)C>C1COCC1>[OH:17][CH:16]([C:14]1[S:15][C:11]([C:6]2[CH:7]=[CH:8][C:9](=[O:10])[N:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=2)=[CH:12][CH:13]=1)[CH3:18]A solution of 5-(1-isopropyl-6-oxo-1,6-dihydropyridin-3-yl)thiophene-2-carbaldehyde (0.205 g, 0.829 mmol) in THF (10 mL) was cooled to 0° C. A solution of 1.5M methyl magnesium bromide in diethyl ether (1.65 mL, 2.48 mmol) was added slowly at 0° C. and the mixture was stirred for 2 h at rt. The reaction mixture was quenched with saturated NH4Cl solution (10 mL) and extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with brine solution (10 mL), dried over Na2SO4 and concentrated under vacuum to obtain crude 5-(5-(1-hydroxyethyl)thiophen-2-yl)-1-isopropylpyridin-2(1H)-one as an off-white solid (0.150 g, 71% yield). LC-MS m/z calcd for [M+H]+ 264.1. found 264.1.
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