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

HRID 1884825Notes

Reaction equation

HRID 1884825 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

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)+.

Workup

  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%

Sources & evidence

ORD record
ord-c130c63bdc8745a4871f6c1c72ea3508
Source dataset
uspto-grants-2004_07
Patent number
US06767909B2

Reaction notes

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