3-Aminobenzyl alcohol → {3-[(5-Chloro-4-{[(1S)-1-(3-methoxyphenyl)ethyl]amino}pyrimidin-2-yl)amino]phenyl}methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,5-dichloro-N-[(1S)-1-(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 hours and NaHCO3 (saturated aqueous solution) was added. The organic solvent was removed under vacuum and water/EtOAc was added. 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 (0.81 g, 90%). LCMS for C20H22ClN4O2 (M+H)+: m/z=385.1.

Provenance & Evidence