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

HRID 28539

Reaktionsgleichung

Reaktionsgleichung von HRID 28539
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

Komponenten

6

Edukt 3

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

Produkt 1

HCID 112558106-(5-Chloro-2-methyl-phenyl)-N*4*-p-tolyl-pyrimidine-2,4-diamineAusbeute 98,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-57e3d671ae764e5690a26c19dfd77d63
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419984B2

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