N-bromobutanimide → HCID 67328112, compound

HRID 1846199Notes

Reaction equation

HRID 1846199 reaction equation
[CH2:1]([C:11]1[CH:16]=[C:15]([O:17][CH3:18])[N:14]=[C:13]([N:19]([CH3:21])[CH3:20])[N:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[Br:22]N1C(=O)CCC1=O>C(#N)C>[Br:22][C:16]1[C:11]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])=[N:12][C:13]([N:19]([CH3:20])[CH3:21])=[N:14][C:15]=1[O:17][CH3:18]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67329002HCID 67329002, compound

Product 1

HCID 67328112HCID 67328112, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
23 °C

Procedure

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.

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-a10d01aec06b40cd975eb0af19d93c95
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

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