反応 #1702131

反応方程式

NaHCO3

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

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

2-(3-aminophenyl)ethanol

p-toluenesulfonic acid monohydrate

→

desired product

収率 96.0%

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

収率 96.0%

溶媒

1,4-dioxane

反応条件

後処理

1. 1
   その他The organic solvent was removed under vacuum and water/EtOAc
2. 2
   workup.ADDITIONwas added
3. 3
   その他After layer separation
4. 4
   抽出the aqueous layer was extracted with EtOAc twice
5. 5
   乾燥The combined organic layers were dried over Na2SO4
6. 6
   ろ過filtered
7. 7
   濃縮concentrated (
8. 8
   その他then triturated with cold EtOAc)

実験手順

To a solution of 2,5-dichloro-N-[2-(3-methoxyphenyl)ethyl]pyrimidin-4-amine (0.50 g, 1.7 mmol) (prepared according to Example 8, step A) and 2-(3-aminophenyl)ethanol (0.31 g, 2.3 mmol) (prepared according to Example 22, Step B) in 1,4-dioxane (14.3 mL) was added p-toluenesulfonic acid monohydrate (0.12 g, 0.61 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). The organic solvent was removed under vacuum and water/EtOAc was added. After layer separation, 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 (0.64 g, 96%). LCMS for C21H24ClN4O2 (M+H)+: m/z=399.1.

出典