Triethylamine → N4,N4-dimethyl-N6-(4-methylphenyl)-2,4,6-pyrimidinetriamine

HRID 1352904

Reaktionsgleichung

Reaktionsgleichung von HRID 1352904
Cl[C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[CH:3]=1.Cl.[CH3:18][NH:19][CH3:20].C(N(CC)CC)C>CN(C=O)C>[CH3:18][N:19]([CH3:20])[C:2]1[CH:3]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:5]=[C:6]([NH2:8])[N:7]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 2387486-Chloro-n4-(4-methylphenyl)pyrimidine-2,4-diamine

Produkt 1

HCID 68563652N4,N4-dimethyl-N6-(4-methylphenyl)-2,4,6-pyrimidinetriamineAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

A mixture of 6-chloro-N4-(4-methylphenyl)-2,4-pyrimidinediamine (1.5 g, 6.4 mmol) and N,N-dimethylamine hydrochloride (0.56 g, 7 mmol) and triethylamine (1.4 g, 14 mmol) in DMF (2 mL), was heated at 170° C. for 16 h. The product was filtered out and the organic layer was treated with saturated NaHCO3 (50 mL) and extracted with EtOAC (3×50 mL). The organic layer was washed with brine (2×100 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by chromatography on silica using hexane/EtOAc (1:3), giving the desired product (0.6 g, 40%).

Aufarbeitung

  1. filtrationThe product was filtered out
  2. additionthe organic layer was treated with saturated NaHCO3 (50 mL)
  3. extractionextracted with EtOAC (3×50 mL)
  4. washThe organic layer was washed with brine (2×100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-b5188f43cb5e4634882dcc1047090c6e
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07220775B2

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