4-Chloroaniline → 6-(5-Chloro-2-methoxy-phenyl)-N*2*-(4-chloro-phenyl)-pyrimidine-2,4-diamine

HRID 28549Notes

Reaction equation

HRID 28549 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[C:4]([C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=2[O:16][CH3:17])[N:3]=1.[Cl:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1>C(O)C>[Cl:15][C:13]1[CH:12]=[CH:11][C:10]([O:16][CH3:17])=[C:9]([C:4]2[N:3]=[C:2]([NH:23][C:22]3[CH:24]=[CH:25][C:19]([Cl:18])=[CH:20][CH:21]=3)[N:7]=[C:6]([NH2:8])[CH:5]=2)[CH:14]=1

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 865946002-Chloro-6-(5-chloro-2-methoxy-phenyl)-pyrimidin-4-yl-amine

Product 1

HCID 114852166-(5-Chloro-2-methoxy-phenyl)-N*2*-(4-chloro-phenyl)-pyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred suspension of the hydrochloride salt of 2-chloro-6-(5-chloro-2-methoxy-phenyl)-pyrimidin-4-yl-amine (0.023 g, 0.075 mmol) in ethanol (7.0 ml) was added 4-chloroaniline (0.025 g, 0.20 mmol). The mixture was stirred under reflux for 6 hours. After evaporation of the solvent under reduced pressure, the residue was treated with hydrochloric acid (1.0 M, 10 ml) and stirred for 30 minutes. Filtration provided the hydrochloride salt of 6-(5-chloro-2-methoxy-phenyl)-N*2*-(4-chloro-phenyl)-pyrimidine-2,4-diamine which was treated with methanol (10 ml) and stirred while a solution of sodium carbonate in water (1.0 M, 1 ml) was added. After stirring for 1 hour, solvents were evaporated under reduced pressure. The residual solid was treated with water (10 ml) and stirred for 15 minutes. Filtration provided the title compound (0.019 g, 70% yield) as a white powder. 1H NMR (CDCl3) δ 4.80 (s, 2H, NH2), 6.62 (s, 1H, Ar), 6.94 (d, 1H, J=8.8 Hz, Ar), 6.98 (s, 1H, NH), 7.27-7.30 (m, 2H, Ar), 7.36 (dd, 1H, J=8.8 Hz, J=2.8 Hz, Ar), 7.61-7.63 (m, 2H, Ar), 7.93 (d, 1H, J=2.8 Hz, Ar),

Workup

  1. temperatureunder reflux for 6 hours
  2. customAfter evaporation of the solvent under reduced pressure
  3. additionthe residue was treated with hydrochloric acid (1.0 M, 10 ml)
  4. stirringstirred for 30 minutes
  5. filtrationFiltration

Sources & evidence

ORD record
ord-aa451e0c7af3429c9b3e3bcae5571df3
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Reaction notes

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