Potassium Carbonate → 3-(5-amino-2-methylphenyl)-7-chloro-1-methyl-1,6-naphthyridin-2(1H)-one

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Reaction Conditions

Reaction Steps

6-Chloro-4-methylamino-pyridine-3-carbaldehyde 6 (19.8 g, 116 mmol) was mixed with 2-(5-amino-2-methyl-phenyl)acetic acid methyl ester 7 (27 g, 151 mmol) and potassium carbonate (48.1 g, 348 mmol) in DMF (1 L). The mixture was heated to 100° C. for 16 h. After cooling to rt and removing solvent in vacuo, the crude product was purified using flash chromatography (ethyl acetate:petroleum ether=1:1). The title compound 8 was obtained as a pale solid. 1H NMR (300 MHz, CDCl3) δ 8.56 (s, 1H), 7.63 (s, 1H), 7.27 (s, 1H), 7.06 (d, J=8.1 Hz, 1H), 6.74 (dd, J=2.4, 8.1 Hz, 1H), 6.58 (d, J=2.4 Hz, 1H), 3.71 (s, 2H), 2.10 (s, 3H).

Provenance & Evidence