Reacción #1702117

Ecuación de reacción

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

methanol

acetic acid

NaHCO3

→

desired product

Rendimiento 25.0%

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

Rendimiento 25.0%

Disolventes

water

EtOAc

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling
2. 2
   Filtraciónthe mixture was filtered
3. 3
   Lavadowashed with EtOAc
4. 4
   ConcentraciónThe filtrate was concentrated under vacuum
5. 5
   Otroto give a residue, which
6. 6
   OtroThe organic layer was dried
7. 7
   Concentraciónconcentrated under vacuum
8. 8
   OtroThe resulting crude product was then purified by silica gel column chromatography

Procedimiento

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.

Fuente