4-Chloroaniline → 6-Chloro-N2-(4-chlorophenyl)pyrimidine-2,4-diamine

HRID 28546

Reaction equation

HRID 28546 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.[Cl:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1>O1CCOCC1>[Cl:9][C:4]1[N:3]=[C:2]([NH:15][C:14]2[CH:16]=[CH:17][C:11]([Cl:10])=[CH:12][CH:13]=2)[N:7]=[C:6]([NH2:8])[CH:5]=1

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 823874-Pyrimidinamine, 2,6-dichloro-

Product 1

HCID 860043166-Chloro-N2-(4-chlorophenyl)pyrimidine-2,4-diamineYield 42%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2,6-dichloro-pyrimidin-4-yl-amine (0.492 g, 3.0 mmol) and 4-chloro-aniline (1.54 g, 12.0 mmol) in dioxane (25 ml) was heated under reflux for 3 hours. After cooled to room temperature, the mixture was filtered. Concentration of the filtrate under reduced pressure provided the crude product which was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:3) to provide 6-chloro-N*2*-(4-chloro-phenyl)-pyrimidine-2,4-diamine (0.32 g, 42% yield) as a white powder.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. filtrationthe mixture was filtered
  4. customConcentration of the filtrate under reduced pressure provided the crude product which
  5. customwas purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:3)

Sources & evidence

ORD record
ord-9eb5e6401f8f42b0be4eb920452e57df
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Linked notes

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