Hydrazinium hydrate → 4-(4-Aminobenzylamino)-N-(4,6-dimethylpyrimidin-2-yl)-benzenesulfonamide

HRID 1884825

Reaktionsgleichung

Reaktionsgleichung von HRID 1884825
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=3)=[CH:15][CH:14]=2)(=[O:12])=[O:11])[N:3]=1.O.[NH3+]N>O1CCCC1.[Pd]>[NH2:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][NH:19][C:16]2[CH:15]=[CH:14][C:13]([S:10]([NH:9][C:4]3[N:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[N:5]=3)(=[O:12])=[O:11])=[CH:18][CH:17]=2)=[CH:22][CH:23]=1

Komponenten

5

Edukt 2

HCID 22629909Hydrazinium hydrateHCID 23504906N-(4,6-dimethylpyrimidin-2-yl)-4-(4-nitrobenzylamino)-benzenesulfonamide

Produkt 1

HCID 235048974-(4-Aminobenzylamino)-N-(4,6-dimethylpyrimidin-2-yl)-benzenesulfonamideAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

18 mg (0.04 mmol) of N-(4,6-dimethylpyrimidin-2-yl)-4-(4-nitrobenzylamino)-benzenesulfonamide was dissolved in 1 ml of tetrahydrofurane. Hydrazinium hydrate (50 μl, 1.5 mmol) and catalytic amount of palladium on charcoal were added to the reaction mixture. Solution was stirred overnight. The reaction mixture was evaporated to dryness and purified on silica using gradient elution (chloroform to 4% methanol in chloroform) to obtain with a yield of 59%. MS (ESI+): m/z 406 (M+H)+, 384 (M+H)+.

Aufarbeitung

  1. customThe reaction mixture was evaporated to dryness
  2. custompurified on silica using gradient elution (chloroform to 4% methanol in chloroform)
  3. customto obtain with a yield of 59%

Quellen und Nachweise

ORD-Eintrag
ord-c130c63bdc8745a4871f6c1c72ea3508
Quelldatensatz
uspto-grants-2004_07
Patentnummer
US06767909B2

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