4-Chloroaniline → (2-Chloro-6-methyl-pyrimidin-4-yl)-(4-chloro-phenyl)-amine

HRID 1514348Notes

Reaction equation

HRID 1514348 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH3:9])[N:3]=1.[Cl:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1.C(N(C(C)C)CC)(C)C>C(#N)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:15][C:14]2[CH:16]=[CH:17][C:11]([Cl:10])=[CH:12][CH:13]=2)[CH:5]=[C:4]([CH3:9])[N:3]=1

Participants

5

Reactant 3

HCID 78124-ChloroanilineHCID 794712,4-Dichloro-6-methylpyrimidineHCID 81531Diisopropylethylamine

Product 1

HCID 58026187(2-Chloro-6-methyl-pyrimidin-4-yl)-(4-chloro-phenyl)-amineYield 10%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

2,4-Dichloro-6-methylpyrimidine (10 g, 61.3 mmol) and 4-chloroaniline (7.83 g, 61.3 mmol) were dissolved in acetonitrile (100 mL). Diisopropylethylamine (21.37 mL, 122.7 mmol) was added and heated to 90° C. for 4 days. The reaction mixture was concentrated in vacuo and the crude product was purified by flash chromatography with ethyl acetate-hexane as eluent to give (2-chloro-6-methyl-pyrimidin-4-yl)-(4-chloro-phenyl)-amine (1.5 g, 10%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe crude product was purified by flash chromatography with ethyl acetate-hexane as eluent

Sources & evidence

ORD record
ord-ec249a4fd41f4774b437844839ec1c19
Source dataset
uspto-grants-2012_07
Patent number
US08222262B2

Reaction notes

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