Ammonium Hydroxide → C-[4-(2,2-Difluoro-propoxy)-pyrimidin-5-yl]-methylamine

Participants

Reaction Steps

4-(2,2-difluoropropoxyl)pyrimidine-5-carbonitrile (1.0 equiv.) was dissolved in a 1:1 mixture of ethanol and ethyl acetate (0.2 M). Sponge nickel catalyst (50% aqueous slurry) (19 equiv.) and ammonium hydroxide (12 equiv.) were added to the reaction vessel, which was purged thoroughly with hydrogen gas and allowed to stir at room temperature for 16 h. The reaction mixture was filtered through a microfiber filter containing celite, washed with ethanol, and volatile solvents were removed under reduced pressure. The residue was purified using silica gel chromatography (60-100% ethyl acetate in hexanes followed by 1-20% MeOH in ethyl acetate). The desired fractions were combined and volatile solvents were removed under reduced pressure to afford (4-(2,2-difluoropropoxyl)pyrimidin-5-yl)methanamine (82% yield). MS(ESI) m/z 204.1 [M+1]+.

Provenance & Evidence