Methyl iodide → (Z)-1,7-dimethyl-3-(2-methyl-5-(1-(methylthio)-3-oxo-3-(thiazol-2-yl)prop-1-enylamino)phenyl)-1,6-naphthyridin-2(1H)-one

Participants

Reaction Steps

To a solution of 1-(thiazol-2-yl)ethanone (24.0 mg, 0.2 mmol) and NaH (16.0 mg, 0.4 mmol, 60% in mineral oil) in DMF (1 mL) was added 3-(5-isothiocyanato-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one 19 (64.5 mg, 0.2 mmol) at rt. The reaction was stirred for 1 h at rt. Then MeI (29 mg, 0.20 mmol) was added. The reaction was quenched with water after 10 min and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to yield crude (Z)-1,7-dimethyl-3-(2-methyl-5-(1-(methylthio)-3-oxo-3-(thiazol-2-yl)prop-1-enylamino)phenyl)-1,6-naphthyridin-2(1H)-one 32 which was used without purification. MS m/z 463.1 (M+1).

Provenance & Evidence