4-Bromoaniline → N*4*-(4-Bromo-phenyl)-6-(2,5-dichloro-phenyl)-pyrimidine-2,4-diamine

HRID 28537Notes

Reaction equation

HRID 28537 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=2[Cl:15])[N:5]=[C:4]([NH2:16])[N:3]=1.[Br:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1.C(OCC)(=O)C>C(O)C>[Br:17][C:18]1[CH:24]=[CH:23][C:21]([NH:22][C:2]2[CH:7]=[C:6]([C:8]3[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=3[Cl:15])[N:5]=[C:4]([NH2:16])[N:3]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 78074-BromoanilineHCID 8857Ethyl AcetateHCID 865945994-Chloro-6-(2,5-dichloro-phenyl)-pyrimidin-2-yl-amine

Product 1

HCID 11441232N*4*-(4-Bromo-phenyl)-6-(2,5-dichloro-phenyl)-pyrimidine-2,4-diamineYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the hydrochloride salt of 4-chloro-6-(2,5-dichloro-phenyl)-pyrimidin-2-yl-amine (0.03 g, 0.096 mmol) and 4-bromoaniline (0.034 g, 0.020 mmol) in ethanol (7.5 ml) was heated under reflux for 1 hour. After evaporation of the solvent under reduced pressure, the residue was treated with 1.0 N hydrochloric acid (10 ml) and stirred for 30 minutes. Filtration provided the crude product, which was treated with ethyl acetate (10 ml) and stirred for 1 hour. After filtration the solid was dissolved in methanol (10 ml) and treated with aqueous sodium carbonate solution (1.0 M, 1 ml). After stirring for 1 hour, the solvent was evaporated under reduced pressure and the solid was treated with water (10 ml). After stirring for 15 minutes, filtration provided the title compound (59% yield) as a white powder. 1H NMR (DMSO-d6) δ 6.31 (s, 1H, Ar), 6.54 (s, 2H, NH2), 7.45 (d, 2H, J=8.9 Hz, Ar), 7.52 (dd, 1H, J=8.6 Hz, J-2.6 Hz, Ar), 7.60 (d, 1H, J=8.6 Hz, Ar), 7.64 (d, 1H, J=2.6 Hz, Ar), 7.77 (d, 2H, J=8.9 Hz, Ar), 9.46 (s, 1H, NH).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. customAfter evaporation of the solvent under reduced pressure
  4. additionthe residue was treated with 1.0 N hydrochloric acid (10 ml)
  5. filtrationFiltration
  6. customprovided the crude product, which
  7. stirringstirred for 1 hour
  8. filtrationAfter filtration the solid
  9. dissolutionwas dissolved in methanol (10 ml)
  10. additiontreated with aqueous sodium carbonate solution (1.0 M, 1 ml)
  11. stirringAfter stirring for 1 hour
  12. customthe solvent was evaporated under reduced pressure
  13. additionthe solid was treated with water (10 ml)
  14. stirringAfter stirring for 15 minutes
  15. filtrationfiltration

Sources & evidence

ORD record
ord-b863c566d9d045fd9293cb99e8b1f630
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Reaction notes

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