4,6-Dichloro-n-methylpyrimidin-2-amine → N-(6-chloro-2-methylamino-pyrimidin-4-yl)-3-trifluoromethyl-benzenesulfonamide

HRID 610824Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 610824
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([NH:9][CH3:10])[N:3]=1.[K+].[F:12][C:13]([F:25])([F:24])[C:14]1[CH:15]=[C:16]([S:20]([NH-:23])(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=1>CN1CCCC1=O>[Cl:1][C:2]1[N:3]=[C:4]([NH:9][CH3:10])[N:5]=[C:6]([NH:23][S:20]([C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([C:13]([F:12])([F:25])[F:24])[CH:15]=2)(=[O:21])=[O:22])[CH:7]=1

Komponenten

4

Edukt 2

HCID 2598804,6-Dichloro-n-methylpyrimidin-2-amineHCID 1317213263-Trifluoromethyl-benzenesulfonamide potassium salt

Produkt 1

HCID 19353537N-(6-chloro-2-methylamino-pyrimidin-4-yl)-3-trifluoromethyl-benzenesulfonamideAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

0.27 g (0.00155 mol) of (4,6-dichloro-pyrimidin-2-yl)-methylamine and 0.82 g (0.0031 mol) of 3-trifluoromethyl-benzenesulfonamide potassium salt were stirred in 10 ml of 1-methyl-2-pyrrolidone at 150° C. for 8 hours. Then, the solvent was distilled off in a high vacuum, the residue was partitioned in ethyl acetate/water and extracted. The aqueous phase was made acid with 4N HCl and extracted with dichloromethane. The residue was chromatographed over silica gel with cyclohexane/ethyl acetate 2:1 as the eluent. There was obtained 0.26 g (69%) of N-(6-chloro-2-methylamino-pyrimidin-4-yl)-3-trifluoromethyl-benzenesulfonamide as white/beige crystals; m.p.: 190-193° C.

Aufarbeitung

  1. distillationThen, the solvent was distilled off in a high vacuum
  2. customthe residue was partitioned in ethyl acetate/water
  3. extractionextracted
  4. extractionextracted with dichloromethane
  5. customThe residue was chromatographed over silica gel with cyclohexane/ethyl acetate 2:1 as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-eda240dd4d5f403586636562c8bb63b2
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998665

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