N-bromobutanimide → HCID 67329292, compound

HRID 1846201Notes

Reaction equation

HRID 1846201 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

HCID 67184N-bromobutanimideHCID 67328833HCID 67328833, compound

Product 1

HCID 67329292HCID 67329292, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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.

Workup

  1. concentrationThe reaction mixture was concentrated under diminished pressure
  2. dissolutionthe residue was dissolved into 100 mL of ethyl acetate
  3. washThe organic solution was washed with a 100-mL portion of brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under diminished pressure
  6. customThe residue was purified by chromatography on a silica gel column
  7. washElution with 9:1 hexanes-ethyl ether

Sources & evidence

ORD record
ord-de6d2204e4b64a0ca691b659f537217d
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

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