反応 #1702120

反応方程式

NaHCO3

2,5-dichloro-N-(3-methoxybenzyl)pyrimidin-4-amine

2,5-Dichloro-N-(3-methoxybenzyl)pyrimidin-4-amine

3-(3-aminophenyl)propan-1-ol

p-toluenesulfonic acid monohydrate

→

desired product

収率 64.5%

3-[3-({5-Chloro-4-[(3-methoxybenzyl)amino]pyrimidin-2-yl}amino)phenyl]propan-1-ol

収率 64.5%

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.ADDITIONfollowed by an addition of water and EtOAc
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 under vacuum
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-(3-methoxybenzyl)pyrimidin-4-amine (0.20 g, 0.70 mmol, prepared according to Example 1, step A), 1,4-dioxane (20 mL), 3-(3-aminophenyl)propan-1-ol (0.16 g, 1.0 mmol, prepared according to Example 12, step A & B), and p-toluenesulfonic acid monohydrate (0.049 g, 0.26 mmol). The mixture was heated at 105° C. for 2 days and NaHCO3 (saturated aqueous solution) was added. The organic solvent was removed under vacuum followed by an addition of water and EtOAc. The aqueous layer was extracted with EtOAc twice. The organic layers were combined, dried over Na2SO4, filtered, and concentrated under vacuum. The crude product was purified by silica gel column chromatography to give the desired product (0.18 g, 64%) as a white solid. LCMS for C21H24lN4O2 (M+H)+: m/z=399.1.

出典