N-bromobutanimide → HCID 67329292, compound
Reaction equation
[CH2:1]([C:17]1[CH:22]=[C:21]([O:23][CH3:24])[N:20]=[C:19]([N:25]([CH3:27])[CH3:26])[N:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[Br:28]N1C(=O)CCC1=O>C(#N)C>[Br:28][C:22]1[C:17]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[N:18][C:19]([N:25]([CH3:26])[CH3:27])=[N:20][C:21]=1[O:23][CH3:24]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 23 °C
Procedure
To a stirred solution containing 1.56 g (4.13 mmol) of 4-hexadecyl-6-methoxy-N,N-dimethylpyrimidin-2-amine in 30 mL of acetonitrile were added 888 mg (4.99 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 1.80 g (95%); mp: 66-67° C.; silica gel TLC Rf 0.60 (9:1 hexanes-ethyl ether); 0.86 (t, 3H, J=6.8 Hz), 1.34-1.20 (br m, 26H), 1.65 (quint, 2H, J=7.2 Hz), 2.68 (dd, 2H, J=7.6, 7.6 Hz), 3.12 (s, 6H) and 3.93 (s, 3H); 13C NMR (CDCl3) δ14.10, 26.67, 27.62, 29.34, 39.37, 29.45, 29.57, 29.63, 29.65, 29.68, 29.68, 29.68, 29.68, 29.68, 31.90, 36.71, 36.95, 36.95, 53.98, 91.17, 160.08, 165.07 and 169.06.