Reacción #1702120

Ecuación de reacción

NaHCO3

2,5-dichloro-N-(3-methoxybenzyl)pyrimidin-4-amine

2,5-Dichloro-N-(3-methoxybenzyl)pyrimidin-4-amine

3-(3-aminophenyl)propan-1-ol

p-toluenesulfonic acid monohydrate

→

desired product

Rendimiento 64.5%

3-[3-({5-Chloro-4-[(3-methoxybenzyl)amino]pyrimidin-2-yl}amino)phenyl]propan-1-ol

Rendimiento 64.5%

Disolventes

1,4-dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe organic solvent was removed under vacuum
2. 2
   workup.ADDITIONfollowed by an addition of water and EtOAc
3. 3
   ExtracciónThe aqueous layer was extracted with EtOAc twice
4. 4
   Secadodried over Na2SO4
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated under vacuum
7. 7
   OtroThe crude product was purified by silica gel column chromatography

Procedimiento

Into a reaction flask were added 2,5-dichloro-N-(3-methoxybenzyl)pyrimidin-4-amine (0.20 g, 0.70 mmol, prepared according to Example 1, step A), 1,4-dioxane (20 mL), 3-(3-aminophenyl)propan-1-ol (0.16 g, 1.0 mmol, prepared according to Example 12, step A & B), and p-toluenesulfonic acid monohydrate (0.049 g, 0.26 mmol). The mixture was heated at 105° C. for 2 days and NaHCO3 (saturated aqueous solution) was added. The organic solvent was removed under vacuum followed by an addition of water and EtOAc. The aqueous layer was extracted with EtOAc twice. The organic layers were combined, dried over Na2SO4, filtered, and concentrated under vacuum. The crude product was purified by silica gel column chromatography to give the desired product (0.18 g, 64%) as a white solid. LCMS for C21H24lN4O2 (M+H)+: m/z=399.1.

Fuente