Dimethyl Carbonate → HCID 66653516, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of sodium hydride (60%, 153 mg, 6.36 mmol) in dimethyl carbonate (3.82 mL, 45.4 mmol) at room temperature was slowly added 6′-methoxy-5′-methyl-2,3,5,6-tetrahydro-[1,3′]bipyridinyl-4-one (1 g, 4.54 mmol). The reaction mixture was heated to reflux (90° C.) for 1 h and then cooled to room temperature. The mixture was partitioned between CH2Cl2 and water and a solution of 1N HCl was added cautiously. The aqueous layer was separated and washed with an addition portion of CH2Cl2. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and evaporated to give the crude product, which was purified by flash-chromatography on silica gel (heptane/ethylacetate 3/1) to afford 6′-methoxy-5′-methyl-4-oxo-3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-3-carboxylic acid methyl ester (975 mg, yield 77%) as a white solid. 1H-NMR (400 MHz, DMSO, 298K) (mixture of keto and enol tautomers observed) δ ppm 2.12 (s, 6H) 2.36-2.69 (m, 4H) 3.26-3.96 (m, 20H) 7.34-7.77 (m, 4H) 11.84 (s, 1H). LCMS: [M+H]+=279.1, Rt(3)=1.51 min (tautomer 1) and 1.70 min (tautomer 2).

Provenance & Evidence