تفاعل #1702131

معادلة التفاعل

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

المردود 96.0%

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

المردود 96.0%

المذيبات

1,4-dioxane

ظروف التفاعل

المعالجة

1. 1
   أخرىThe organic solvent was removed under vacuum and water/EtOAc
2. 2
   workup.ADDITIONwas added
3. 3
   أخرىAfter layer separation
4. 4
   استخلاصthe aqueous layer was extracted with EtOAc twice
5. 5
   تجفيفThe combined organic layers were dried over Na2SO4
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated (
8. 8
   أخرىthen triturated with cold EtOAc)

الإجراء التجريبي

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.

المصدر