3-Chlorobenzaldehyde → (E)-3-(4-(3-chlorostyryl)-3-methyl-5-nitro-2,6-dioxo-2,3-dihydropyrimidin-1(6H)-yl)propyl acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(3,4-dimethyl-5-nitro-2,6-dioxo-2,3-dihydropyrimidin-1(6H)-yl)propyl acetate (300 mg, 1.05 mmol) in HOAc (0.7 mL) was added 3-chlorobenzaldehyde (221 mg, 1.58 mmol) and sodium acetate (431 mg, 5.26 mmol). The reaction was heated at 150° C. for 7 h, cooled to RT then diluted with EA (20 mL) and water (20 mL). The organic layer was dried over Na2SO4 and concentrated to a residue which was purified by chromatography PE/EA (5:1 to 2:1) to give (E)-3-(4-(3-chlorostyryl)-3-methyl-5-nitro-2,6-dioxo-2,3-dihydropyrimidin-1 (6H)-yl)propyl acetate (70 mg, 16.4% yield) as a brown oil. LCMS: MH+ 408 and TR=1.560 min.

Provenance & Evidence