Reaction #1702128

Reaction equation

NaHCO3

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

3-aminobenzyl alcohol

p-toluenesulfonic acid monohydrate

→

desired product

Yield 101.7%

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

Yield 101.7%

Solvents

1,4-dioxane

Conditions

Workup

1. 1
   Otherthe organic solvent was removed under vacuum
2. 2
   workup.ADDITIONfollowed by the addition of water and EtOAc
3. 3
   ExtractionThe aqueous layer was extracted with EtOAc twice
4. 4
   DryingThe combined organic layers were dried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated (
7. 7
   Otherthen triturated with cold EtOAc)

Procedure

To a solution of 2,5-dichloro-N-[2-(3-methoxyphenyl)ethyl]pyrimidin-4-amine (0.70 g, 2.3 mmol) and 3-aminobenzyl alcohol (0.39 g, 3.2 mmol) in 1,4-dioxane (20.0 mL) was added p-toluenesulfonic acid monohydrate (0.16 g, 0.85 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) and the organic solvent was removed under vacuum, followed by the addition of water and EtOAc. 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 an off-white powder (0.90 g, 100%). LCMS for C20H22ClN4O2 (M+H)+: m/z=385.1.

Source