Hydrochloric Acid → 6-(5-Chloro-2-methyl-phenyl)-N*4*-p-tolyl-pyrimidine-2,4-diamine

HRID 28539

Reaction equation

HRID 28539 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[CH3:15])[N:5]=[C:4]([NH2:16])[N:3]=1.Cl.[CH3:18][C:19]1[CH:20]=[CH:21][C:22]([NH2:25])=[CH:23][CH:24]=1>C(O)C.O1CCOCC1>[Cl:14][C:12]1[CH:11]=[CH:10][C:9]([CH3:15])=[C:8]([C:6]2[N:5]=[C:4]([NH2:16])[N:3]=[C:2]([NH:25][C:22]3[CH:23]=[CH:24][C:19]([CH3:18])=[CH:20][CH:21]=3)[CH:7]=2)[CH:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7813p-ToluidineHCID 860043474-Chloro-6-(5-chloro-2-methylphenyl)pyrimidin-2-yl-amine

Product 1

HCID 112558106-(5-Chloro-2-methyl-phenyl)-N*4*-p-tolyl-pyrimidine-2,4-diamineYield 98.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred suspension of the hydrochloride salt of 4-chloro-6-(5-chloro-2-methyl-phenyl)-pyrimidin-2-yl-amine (0.01 g, 0.0344 mmol) in ethanol (5 ml) was added a solution of hydrogen chloride in dioxane (4.0 M, 0.01 ml) followed by p-tolylamine (0.074 g, 0.068 mmol). The mixture was heated under reflux for 75 minutes. After evaporation of volatiles under reduced pressure, the residue was treated 1.0 M hydrochloric acid (10 ml) and stirred for 30 minutes. After filtration the solid was dissolved in methanol (5 ml) and treated with a solution of sodium carbonate in water (1.0 M, 1.0 ml). After stirring for 30 minutes volatiles were evaporated under reduced pressure. The residue was treated with water (10 ml) and stirred for 15 minutes. Filtration provided the title compound (0.011 g, 98% yield) as a white powder. 1H NMR (DMSO-d6) δ 2.27 (s, 3H, CH3), 2.34 (s, 3H, CH3), 6.07 (s, 1H, Ar), 6.33 (s, 2H, NH2), 7.10 (d, 2H, J=8.3 Hz, Ar), 7.30 (d, 1H, J=8.2 Hz, Ar), 7.35-7.40 (m, 2H, Ar), 7.61 (d, 1H, J=8.4 Hz, Ar), 9.09 (s, 1H, NH).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 75 minutes
  3. customAfter evaporation of volatiles under reduced pressure
  4. additionthe residue was treated 1.0 M hydrochloric acid (10 ml)
  5. filtrationAfter filtration the solid
  6. dissolutionwas dissolved in methanol (5 ml)
  7. additiontreated with a solution of sodium carbonate in water (1.0 M, 1.0 ml)
  8. stirringAfter stirring for 30 minutes volatiles
  9. customwere evaporated under reduced pressure
  10. additionThe residue was treated with water (10 ml)
  11. stirringstirred for 15 minutes
  12. filtrationFiltration

Sources & evidence

ORD record
ord-57e3d671ae764e5690a26c19dfd77d63
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Linked notes

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