Reaction #1702118

Reaction equation

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

hydrogen chloride

triethylamine

3-nitrobenzoyl chloride

→

desired product

Yield 70.0%

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

Yield 70.0%

Solvents

THF

Conditions

Workup

1. 1
   Concentrationconcentrated under vacuum
2. 2
   OtherThe residue was partitioned in EtOAc
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 (0.10 g, 0.29 mmol) (prepared according to Example 3, step B) and triethylamine (0.16 mL, 1.2 mmol) in THF (3 mL) was added slowly 3-nitrobenzoyl chloride (54 mg, 0.29 mmol). The resulting mixture was stirred at rt for 2 hours and concentrated under vacuum. The residue was partitioned in EtOAc and water. The organic layer was dried over Na2SO4, filtered, and concentrated under vacuum to give the desired product as a yellow solid (90 mg, 70%). LCMS for C18H14Cl2N5O3 (M+H)+: m/z=418.0, 420.0.

Source