Reaction #1702135

Reaction equation

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

3-aminobenzyl alcohol

p-toluenesulfonic acid monohydrate

→

desired product

Yield 80.9%

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

Yield 80.9%

Solvents

1,4-dioxane

Conditions

Workup

1. 1
   TemperatureAfter cooling
2. 2
   Filtrationthe mixture was filtered under vacuum
3. 3
   WashThe cake was washed with cold EtOAc

Procedure

To a solution of 2,5-dichloro-N-[3-(3-methoxyphenyl)propyl]pyrimidin-4-amine (0.70 g, 2.2 mmol) and 3-aminobenzyl alcohol (0.38 g, 3.0 mmol) in 1,4-dioxane (19.1 mL) was added p-toluenesulfonic acid monohydrate (0.16 g, 0.82 mmol). The mixture was heated at 100° C. for 16 hours and the reaction was complete. After cooling, the mixture was filtered under vacuum. The cake was washed with cold EtOAc and then H2O to give the desired product as an off-white powder (0.71 g, 79%). LCMS for C21H24ClN4O2 (M+H)+: m/z=399.1.

Source