Reacción #1702131

Ecuación de reacción

NaHCO3

2,5-dichloro-N-[2-(3-methoxyphenyl)ethyl]pyrimidin-4-amine

2,5-Dichloro-N-[2-(3-methoxyphenyl)ethyl]pyrimidin-4-amine

2-(3-aminophenyl)ethanol

p-toluenesulfonic acid monohydrate

→

desired product

Rendimiento 96.0%

2-{3-[(5-Chloro-4-{[2-(3-methoxyphenyl)ethyl]amino}pyrimidin-2-yl)amino]phenyl}ethanol

Rendimiento 96.0%

Disolventes

1,4-dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe organic solvent was removed under vacuum and water/EtOAc
2. 2
   workup.ADDITIONwas added
3. 3
   OtroAfter layer separation
4. 4
   Extracciónthe aqueous layer was extracted with EtOAc twice
5. 5
   SecadoThe combined organic layers were dried over Na2SO4
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated (
8. 8
   Otrothen triturated with cold EtOAc)

Procedimiento

To a solution of 2,5-dichloro-N-[2-(3-methoxyphenyl)ethyl]pyrimidin-4-amine (0.50 g, 1.7 mmol) (prepared according to Example 8, step A) and 2-(3-aminophenyl)ethanol (0.31 g, 2.3 mmol) (prepared according to Example 22, Step B) in 1,4-dioxane (14.3 mL) was added p-toluenesulfonic acid monohydrate (0.12 g, 0.61 mmol). The mixture was heated at 100° C. for 16 h and the reaction was complete. To the mixture was added NaHCO3 (saturated aqueous solution). The organic solvent was removed under vacuum and water/EtOAc was added. After layer separation, the aqueous layer was extracted with EtOAc twice. The combined organic layers were dried over Na2SO4, filtered, and concentrated (then triturated with cold EtOAc) to give the desired product as a light brown powder (0.64 g, 96%). LCMS for C21H24ClN4O2 (M+H)+: m/z=399.1.

Fuente