4-Methylmorpholine → 3-Ethyl 5-methyl 2-amino-6-methyl-4-(p-tolyl)-1,4-dihydropyridine-3,5-dicarboxylate

Participants

Reaction Steps

A mixture of (E and Z) methyl 2-(4-methylbenzylidene)-3-oxobutanoate (887 mg, 4.06 mmol), ethyl 3,3-diaminoacrylate, hydrochloride (677 mg, 4.06 mmol), and N-methylmorpholine (447 μl, 4.06 mmol) in Isopropanol (7682 μl) was refluxed overnight. The reaction was then concentrated and purified with column chromatography (0-100% EtOAc/Hexane) to afford 3-ethyl 5-methyl 2-amino-6-methyl-4-(p-tolyl)-1,4-dihydropyridine-3,5-dicarboxylate (1.1349 g, 3.44 mmol, 85% yield) as pale yellow solid: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.15 (d, J=8.0 Hz, 2 H), 7.01 (d, J=7.8 Hz, 2 H), 5.90 (br. s., 2 H), 5.64 (s, 1 H), 4.86 (s, 1 H), 4.07 (q, J=7.1 Hz, 2 H), 3.64 (s, 3 H), 2.32 (s, 3 H), 2.27 (s, 3 H), 1.23 (t, 3 H); LCMS (m/z) ES+=331 (M+1).

Provenance & Evidence