2-Ethylaniline → 2-Methylpentane

HRID 347745Notes

Reaction equation

HRID 347745 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[CH2:9]([C:11]1[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=1[NH2:13])[CH3:10].C(N(CC)C(C)C)(C)C>C(O)CCC>[CH3:15][CH2:14][CH2:12][CH:11]([CH3:17])[CH3:9].[Cl:1][C:2]1[N:7]=[C:6]([NH:13][C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=2[CH2:9][CH3:10])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 113572-EthylanilineHCID 775312,4-DichloropyrimidineHCID 81531Diisopropylethylamine

Product 2

HCID 78922-MethylpentaneHCID 179811452-Chloro-4-(2-ethylanilino)pyrimidine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

2,4-Dichloropyrimidine (596 mg, 4 mmol), 2-ethylaniline (494 ml, 4 mmol) and N,N-diisopropylethylamine (695 ml, 4 mmol) were dissolved in n-butanol (20 ml) with stirring. The reaction mixture was heated to 100° C. for 18 hours, allowed to cool to ambient temperature and evaporated onto silica (3 ml). The residue was purified by column chromatography eluting with EtOAc (0–20%): isohexane to give the title product as a colourless solid on evaporation (215 mg, 23%). NMR (CDCl3, 300 MHz): 1.20 (t, 3H), 2.61 (q, 2H), 6.26 (d, 1H), 6.80 (br, 1H) 7.31 (m, 4H), 8.04 (d, 1H); m/z: (ES−) 234.2 (MH+).

Workup

  1. temperatureto cool to ambient temperature
  2. customevaporated onto silica (3 ml)
  3. customThe residue was purified by column chromatography
  4. washeluting with EtOAc (0–20%)

Sources & evidence

ORD record
ord-c981408d6e2c4cafa0eed54994b5d123
Source dataset
uspto-grants-2007_02
Patent number
US07176212B2

Reaction notes

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