Morpholine → N-(6-bromo-2-morpholinopyrimidin-4-yl)quinolin-3-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,4,6-tribromopyrimidine (5.40 g, 17.2 mmol) in acetonitrile (60 mL) was added quinolin-3-amine, followed by DIEA (8.99 mL, 51.6 mmol). The reaction mixture was heated to 45° C. overnight. Morpholine (1.50 mL, 17.2 mmol) was then added, and the reaction mixture continued heating for 4 h. The reaction mixture was then cooled to room temperature, concentrated and dissolved in EtOAc (about 500 mL), the organic solution was washed with saturated NaHCO3 (3×), H2O (2×), brine (1×) and dried over Na2SO4. The solution was then evaporated in the presence of silica gel and purified by column chromatography (SiO2, 15-25% EtOAc/Hexanes) to yield N-(6-bromo-2-morpholinopyrimidin-4-yl)quinolin-3-amine. LC/MS (m/z): 386.1 (MH+).

Provenance & Evidence