6-(2-(dimethylamino)vinyl)-1-methyl-5-nitro-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)pyrimidine-2,4(1H,3H)-dione → 3-(1-methyl-2,4-dioxo-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-(2-(dimethylamino)vinyl)-1-methyl-5-nitro-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)pyrimidine-2,4(1H,3H)-dione (530 mg, 1.4 mmol) in HOAc (5 mL) was added Zn dust (910 mg, 14 mmol). The reaction was heated at 100° C. for 2 h, cooled to RT, diluted with water (10 mL) and extracted with EA (3×20 mL). The combined organic layers were dried over Na2SO4 and concentrated to a residue which was purified by chromatography eluted with PE/EA (1:1) to give 3-(1-methyl-2,4-dioxo-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate (210 mg, 56% yield) as a white solid. LCMS: MH+ 266 and TR=0.646 min.

Provenance & Evidence