3,4-Dichloroaniline → 4,6-dichloro-N-(3,4-dichlorophenyl)-2-pyrimidinamine

HRID 1352884Notes

Reaction equation

HRID 1352884 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.[Cl:10][C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][C:17]=1[Cl:18])[NH2:14]>O1CCOCC1.C(N(CC)C(C)C)(C)C>[Cl:9][C:4]1[CH:5]=[C:6]([Cl:8])[N:7]=[C:2]([NH:14][C:13]2[CH:15]=[CH:16][C:17]([Cl:18])=[C:11]([Cl:10])[CH:12]=2)[N:3]=1

Participants

5

Reactant 2

HCID 72573,4-DichloroanilineHCID 773782,4,6-Trichloropyrimidine

Product 1

HCID 211013154,6-dichloro-N-(3,4-dichlorophenyl)-2-pyrimidinamineYield 58%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 81531DiisopropylethylamineSolvent

Procedure

A solution of 2,4,6-trichloropyrimidine (5.00 g), 3,4-dichloroaniline (4.45 g, 1 equivalent) in 1,4-dioxane (20 mL) and N,N-diisopropylethylamine (10 mL) was heated at reflux with stirring for 3 hours. The solvent was removed and the crude material was purified by flash chromatography on silica gel. The column was eluted with a gradient of cyclohexane to ethyl acetate/cyclohexane (1:9). The eluent was removed, giving 4,6-dichloro-N-(3,4-dichlorophenyl)-2-pyrimidinamine (1.83 g, 58%, Rf=0.39 in ethyl acetate/cyclohexane, 2:3).

Workup

  1. temperatureat reflux
  2. customThe solvent was removed
  3. customthe crude material was purified by flash chromatography on silica gel
  4. washThe column was eluted with a gradient of cyclohexane to ethyl acetate/cyclohexane (1:9)
  5. customThe eluent was removed

Sources & evidence

ORD record
ord-a1284ffd615c47f6ba38763cc864661a
Source dataset
uspto-grants-2007_05
Patent number
US07220775B2

Reaction notes

Loading…