Reaction #1702116

Reaction equation

N-(3-aminobenzyl)-2,5-dichloropyrimidin-4-amine

hydrogen chloride

triethylamine

m-nitrobenzenesulfonyl chloride

→

desired product

Yield 95.0%

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

Yield 95.0%

Solvents

THF

Conditions

Workup

1. 1
   Otherthe solvent was removed under vacuum
2. 2
   workup.ADDITIONThe residue was treated with EtOAc and water
3. 3
   DryingThe organic layer was dried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated under vacuum

Procedure

To a mixture of N-(3-aminobenzyl)-2,5-dichloropyrimidin-4-amine.hydrogen chloride (0.20 g, 0.58 mmol) and triethylamine (0.32 mL, 2.3 mmol) in THF (3 mL) was added slowly m-nitrobenzenesulfonyl chloride (0.13 g, 0.58 mmol). The resulting mixture was stirred at rt for 2 hours and the solvent was removed under vacuum. The residue was treated with EtOAc and water. The organic layer was dried over Na2SO4, filtered, and concentrated under vacuum to provide the desired product (0.30 g, 95%). LCMS for C17H14Cl2N5O4S (M+H)+: m/z=453.9, 455.9.

Source