Dimethylformamide dimethyl acetal → 6-(2-(dimethylamino)vinyl)-1-methyl-5-nitro-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)pyrimidine-2,4(1H,3H)-dione

Participants

Reaction Conditions

Reaction Steps

To a solution of 1,6-dimethyl-5-nitro-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)pyrimidine-2,4(1H,3H)-dione (980 mg, 3 mmol) in DMF (2 mL) was added DMF-DMA (5 mL). The reaction was heated at 95° C. for 15 h, cooled to RT and concentrated to a residue which was dissolved in EA (20 mL). The mixture was washed with aq. 1N LiCl (3×10 mL). The organic layer was dried over Na2SO4 and concentrated to a residue which was purified by chromatography eluted with PE/EA (2:1) to give 6-(2-(dimethylamino)vinyl)-1-methyl-5-nitro-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl) pyrimidine-2,4(1H,3H)-dione (840 mg, 73% yield) as a yellow oil. LCMS: MH+ 383 and TR=1.308 min.

Provenance & Evidence