Reaction #1702117

Reaction equation

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

methanol

acetic acid

NaHCO3

→

desired product

Yield 25.0%

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

Yield 25.0%

Solvents

water

EtOAc

Conditions

Workup

1. 1
   TemperatureAfter cooling
2. 2
   Filtrationthe mixture was filtered
3. 3
   Washwashed with EtOAc
4. 4
   ConcentrationThe filtrate was concentrated under vacuum
5. 5
   Otherto give a residue, which
6. 6
   OtherThe organic layer was dried
7. 7
   Concentrationconcentrated under vacuum
8. 8
   OtherThe resulting crude product was then purified by silica gel column chromatography

Procedure

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.

Source