2,4-Difluoroaniline → 2-Methylpentane

HRID 347737Notes

Reaction equation

HRID 347737 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[F:9][C:10]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:11]=1[NH2:12].C(N(C(C)C)CC)(C)C>C(O)CCC>[CH3:6][CH2:5][CH2:4][CH:10]([CH3:16])[CH3:11].[Cl:1][C:2]1[N:7]=[C:6]([NH:12][C:11]2[CH:13]=[CH:14][C:15]([F:17])=[CH:16][C:10]=2[F:9])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 97092,4-DifluoroanilineHCID 775312,4-DichloropyrimidineHCID 81531Diisopropylethylamine

Product 2

HCID 78922-MethylpentaneHCID 179811362-Chloro-4-(2,4-difluoroanilino)pyrimidine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

2,4-Dichloropyrimidine (200 mg, 1.34 mmol), 2,4-difluoroaniline (173 mg, 1.34 mmol) and diisopropylethylamine (0.26 ml, 1.48 mmol) were dissolved in n-butanol (5 ml). 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 solid on evaporation (174 mg, 54%). NMR (300 MHz): 6.70 (d, 1H), 7.12 (t, 1H), 7.38 (t, 1H), 7.70 (dd, 1H), 8.14 (d, 1H), 9.74 (brs, 1H); m/z: (ES+) 242.1 (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-f6da5a729c2e494ebc8fa4f7327d1432
Source dataset
uspto-grants-2007_02
Patent number
US07176212B2

Reaction notes

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