Reacción #1702115

Ecuación de reacción

tert-butyl [3-(aminomethyl)phenyl]carbamate

2,4,5-trichloropyrimidine

potassium carbonate

→

desired product

Rendimiento 92.3%

tert-Butyl(3-{[(2,5-dichloropyrimidin-4-yl)amino]methyl}phenyl)carbamate

Rendimiento 92.3%

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was quenched with water
2. 2
   workup.ADDITIONEtOAc was added
3. 3
   Otrothe layers were separated
4. 4
   ExtracciónThe aqueous layer was extracted with EtOAc twice
5. 5
   LavadoThe combined organic layers were washed with water and brine successively
6. 6
   Secadodried (Na2SO4)
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated
9. 9
   OtroThe resulted residue was triturated with methylene chloride and hexanes

Procedimiento

To a solution of tert-butyl [3-(aminomethyl)phenyl]carbamate (0.50 g, 2.2 mmol) and 2,4,5-trichloropyrimidine (0.45 g, 2.5 mmol) in N,N-dimethylformamide (6 mL) was added potassium carbonate (0.62 g, 4.5 mmol). The resultant mixture was stirred overnight at room temperature. The reaction was quenched with water. EtOAc was added and the layers were separated. The aqueous layer was extracted with EtOAc twice. The combined organic layers were washed with water and brine successively, then dried (Na2SO4), filtered, and concentrated. The resulted residue was triturated with methylene chloride and hexanes to give the desired product as an off-white powder (0.75 g, 90%). LCMS for C12H11Cl2N4O2 (M-tBu+H)+: m/z=313.0, 315.0.

Fuente