Reaktion #1702117

Reaktionsgleichung

N-(3-{[(2,5-dichloropyrimidin-4-yl)amino]methyl}phenyl)-3-nitrobenzenesulfonamide

methanol

acetic acid

NaHCO3

→

desired product

Ausbeute 25.0%

3-Amino-N-(3-{[(2,5-dichloropyrimidin-4-yl)amino]methyl}phenyl)benzenesulfonamide

Ausbeute 25.0%

Lösungsmittel

water

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Filtrationthe mixture was filtered
3. 3
   Waschenwashed with EtOAc
4. 4
   EinengenThe filtrate was concentrated under vacuum
5. 5
   Sonstigeto give a residue, which
6. 6
   SonstigeThe organic layer was dried
7. 7
   Einengenconcentrated under vacuum
8. 8
   SonstigeThe resulting crude product was then purified by silica gel column chromatography

Vorschrift

Into a reaction flask was added N-(3-{[(2,5-dichloropyrimidin-4-yl)amino]methyl}phenyl)-3-nitrobenzenesulfonamide (0.20 g, 0.44 mmol), methanol (20 mL), acetic acid (2.0 mL), and water (1 mL). Then iron (0.25 g, 4.5 mmol) powder was added. The reaction mixture was heated at 70° C. for 2 hours. After cooling, the mixture was filtered and washed with EtOAc. The filtrate was concentrated under vacuum to give a residue, which was treated with NaHCO3 (saturated aqueous solution) and EtOAc. The organic layer was dried and concentrated under vacuum. The resulting crude product was then purified by silica gel column chromatography to provide the desired product (46 mg, 25%). LCMS for C17H16Cl2N5O2S (M+H)+: m/z=424.0, 426.0.

Quelle