N-bromobutanimide → HCID 67328038, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution containing 1.41 g (3.99 mmol) of 4-methoxy-6-(10-(methoxymethoxy)decyl)-N,N-dimethylpyrimidin-2-amine in 10 mL of acetonitrile were added 852 mg (4.79 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 acetate afforded the expected product as colorless oil: yield 910 mg (53%); silica gel TLC Rf 0.65 (9:1 hexanes-ethyl acetate); 1H NMR (CDCl3) δ 1.31-1.26 (br m, 10H), 1.54-1.64 (m, 4H), 2.67 (dd, 2H, J=7.6, 7.6 Hz), 3.11 (s, 6H), 3.33 (s, 3H), 3.48 (t, 2H, J=6.8 Hz), 3.92 (s, 3H) and 4.59 (s, 2H); 13C-NMR (CDCL3) δ 26.18, 27.59, 29.34, 29.40, 29.40, 29.47, 29.55, 29.72, 36.68, 36.93, 53.96, 55.04, 67.85, 91.16, 96.35, 160.06, 165.05 and 169.04; mass spectrum (APCI+), m/z 432.1857 (M+H) (C19H35N3O3Br requires 432.1862).

Provenance & Evidence