N-bromobutanimide → HCID 67328112, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution containing 1.22 g (4.16 mmol) of 4-decyl-6-methoxy-N,N-dimethylpyrimidin-2-amine in 20 mL of acetonitrile were added 808 mg (4.54 mmol) of N-bromosuccinimide. The reaction mixture was stirred at 23° C. and protected from light for 5 h. The reaction mixture was concentrated under diminished pressure and the residue was dissolved into 100 mL of ethyl acetate. The organic solution was washed with a 100-mL portion of brine, dried (MgSO4) and concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column. Elution with 9:1 hexanes-ethyl ether afforded the expected product as white solid: yield 1.27 g (82%); mp: 45-46° C.; silica gel TLC Rf 0.75 (9:1 hexanes-ethyl ether); 1H-NMR (CDCl3) δ 0.86 (t, 3H, J=6.8 Hz), 1.33-1.24 (br m, 14H), 1.65 (quint, 2H, J=7.2 Hz), 2.68 (dd, 2H, J=7.6, 7.6 Hz), 3.12 (s, 6H) and 3.92 (s, 3H); 13C NMR (CDCl3) δ 14.09, 22.67, 27.62, 29.32, 29.37, 29.45, 29.57, 29.60, 31.89, 36.70, 36.94, 36.94, 53.97, 91.17, 160.07, 165.06 and 169.05.

Provenance & Evidence