2,5-Dimethylaniline → 2-Methylpentane

HRID 347735

Reaction equation

HRID 347735 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[CH3:9][C:10]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:11]=1[NH2:12].C(N(CC)CC)C>CCO>[CH3:14][CH2:13][CH2:11][CH:10]([CH3:16])[CH3:9].[Cl:1][C:2]1[N:7]=[C:6]([NH:12][C:11]2[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:10]=2[CH3:9])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 72592,5-DimethylanilineHCID 8471TriethylamineHCID 775312,4-Dichloropyrimidine

Product 2

HCID 78922-MethylpentaneHCID 113108502-Chloro-4-(2,5-dimethylanilino)pyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,4-Dichloropyrimidine (500 mg, 3.36 mmol), 2,5-dimethylaniline (407 mg, 3.36 mmol) and triethylamine (0.51 ml, 3.69 mmol) were dissolved in EtOH (5 ml) with stirring. The reaction mixture was heated at reflux for 12 hours, cooled and evaporated onto silica (5 ml). The residue was purified by column chromatography and eluted with EtOAc (30%): isohexane to give the title product as a waxy solid on evaporation (514 mg, 66%). NMR (300 MHz): 2.1 (s, 3H), 2.27 (s, 3H), 6.42 (d. 1H), 6.99 (d, 1H), 7.08 (s, 1H). 7.18 (d, 1H), 8.03 (d, 1H), 9.45 (s, 1H); m/z: (ES+) 234.3 (MH+).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 12 hours
  3. temperaturecooled
  4. customevaporated onto silica (5 ml)
  5. customThe residue was purified by column chromatography
  6. washeluted with EtOAc (30%)

Sources & evidence

ORD record
ord-36c0c7568fde4d02bed8f71c2b1944d0
Source dataset
uspto-grants-2007_02
Patent number
US07176212B2

Linked notes

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