反応 #1702123

反応方程式

NaHCO3

2,5-dichloro-N-[(1R)-1-(3-methoxyphenyl)ethyl]pyrimidin-4-amine

3-aminobenzyl alcohol

p-toluenesulfonic acid monohydrate

→

desired product

収率 100.2%

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

収率 100.2%

溶媒

1,4-dioxane

反応条件

後処理

1. 1
   その他the organic solvent was removed under vacuum
2. 2
   workup.ADDITIONWater and EtOAc were added to the residue
3. 3
   抽出The aqueous layer was extracted with EtOAc twice
4. 4
   乾燥dried over Na2SO4
5. 5
   ろ過filtered
6. 6
   濃縮concentrated
7. 7
   その他The crude product was purified by silica gel column chromatography

実験手順

Into a reaction flask were added 2,5-dichloro-N-[(1R)-1-(3-methoxyphenyl)ethyl]pyrimidin-4-amine (0.21 g, 0.70 mmol), 1,4-dioxane (20 mL), 3-aminobenzyl alcohol (0.13 g, 1.0 mmol), and p-toluenesulfonic acid monohydrate (0.049 g, 0.26 mmol). The mixture was heated at 105° C. for 2 days. To the reaction mixture was added NaHCO3 (saturated aqueous solution) and the organic solvent was removed under vacuum. Water and EtOAc were added to the residue. The aqueous layer was extracted with EtOAc twice. The organic layers were combined, dried over Na2SO4, filtered, and concentrated. The crude product was purified by silica gel column chromatography to give the desired product (0.27 g, 96%). LCMS for C20H22ClN4O2 (M+H)+: m/z=385.1.

出典