2-Bromo-4-methylaniline → 2-Methylpentane

HRID 347741Notes

Reaction equation

HRID 347741 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[Br:9][C:10]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:11]=1[NH2:12].C(N(C(C)C)CC)(C)C>C(O)CCC>[CH3:11][CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16].[Cl:1][C:2]1[N:7]=[C:6]([NH:12][C:11]2[CH:13]=[CH:14][C:15]([CH3:17])=[CH:16][C:10]=2[Br:9])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 114222-Bromo-4-methylanilineHCID 775312,4-DichloropyrimidineHCID 81531Diisopropylethylamine

Product 2

HCID 78922-MethylpentaneHCID 17981144HCID 17981144, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

2,4-Dichloropyrimidine (1 g, 6.71 mmol), 2-bromo-4-methylaniline (1.25 g, 6.71 mmol) and di-isopropylethylamine (1.29 ml, 7.38 mmol) were dissolved in n-butanol (5 ml). The reaction mixture was heated at 120° C. 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 solid on evaporation (1.01 g). NMR (300 MHz): 2.31 (s, 3H), 6.50 (d, 1H), 7.22 (dd, 1H), 7.36 (d, 1H), 7.55 (s, 1H), 8.09 (d, 1H), 9.61 (s, 1H); m/z: (ES+) 298.1 (MH+).

Workup

  1. temperaturecooled
  2. customevaporated onto silica (5 ml)
  3. customThe residue was purified by column chromatography
  4. washeluted with EtOAc (30%)

Sources & evidence

ORD record
ord-1adcf999a79647d6a2683ece9512052d
Source dataset
uspto-grants-2007_02
Patent number
US07176212B2

Reaction notes

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