Methyl iodide → methyl 3-(6-bromo-1-methyl-2,4-dioxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propanoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-2-(3-(3-methoxy-3-oxopropyl)ureido)nicotinic acid (15 g, 43.5 mmol) in acetone (150 mL) was added K2CO3 (18 g, 130.4 mmol) followed by CH3I (18 mL, 263.1 mmol). The reaction was heated in a sealed flask at 40° C. for 24 h, cooled to RT, concentrated then diluted with EA (200 mL) and water (100 ml). The organic layer was washed with brine (100 mL), dried over Na2SO4, filtered and concentrated to a residue which was purified by chromatography PE/EA eluted with (10:1 to 2:1) to give methyl 3-(6-bromo-1-methyl-2,4-dioxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propanoate (5.1 g, 34.4% yield) as a white solid. LCMS: MH+ 342 and TR=1.266 min. Used without further purification.

Provenance & Evidence