Triethylamine → N-(2,6-bis-methylamino-pyrimidin-4-yl)-4-fluoro-benzenesulfonamide

HRID 378291Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 378291
Cl[C:2]1[N:7]=[C:6]([NH:8][CH3:9])[N:5]=[C:4]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:3]=1.Cl.CN.[CH2:24]([N:26](CC)CC)C>C(O)C>[CH3:9][NH:8][C:6]1[N:5]=[C:4]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:3]=[C:2]([NH:26][CH3:24])[N:7]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 6364545Methylamine hydrochlorideHCID 19353544N-(6-chloro-2-methylamino-pyrimidin-4-yl)-4-fluoro-benzenesulfonamide

Produkt 1

HCID 17774522N-(2,6-bis-methylamino-pyrimidin-4-yl)-4-fluoro-benzenesulfonamideAusbeute 43,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

0.36 g (0.0011 mol) of N-(6-chloro-2-methylamino-pyrimidin-4-yl)-4-fluoro-benzenesulfonamide was dissolved in 10 ml of ethanol, treated with 1.2 g (0.018 mol) of methylamine hydrochloride and 4.0 ml (0.029 mol) of triethylamine and stirred in an autoclave at 140° C. for 17 hours. The mixture was freed completely from solvent, the residue was partitioned in ethyl acetate/water, the insoluble constituents were filtered off under suction and extracted. The extract and the solid were combined and recrystallized from methanol/diethyl ether. There was obtained 0.15 g (43%) of N-(2,6-bis-methylamino-pyrimidin-4-yl)-4-fluoro-benzenesulfonamide as white crystals; m.p. 261-263° C.

Aufarbeitung

  1. customthe residue was partitioned in ethyl acetate/water
  2. filtrationthe insoluble constituents were filtered off under suction
  3. extractionextracted
  4. extractionThe extract
  5. customrecrystallized from methanol/diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-e43e829c2ce54c36ab02dad425a4882b
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06030976

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