反应 #1702120

反应方程式

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

收率 64.5%

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

收率 64.5%

溶剂

1,4-dioxane

反应条件

后处理

1. 1
   其他The organic solvent was removed under vacuum
2. 2
   workup.ADDITIONfollowed by an addition of water and EtOAc
3. 3
   萃取The aqueous layer was extracted with EtOAc twice
4. 4
   干燥dried over Na2SO4
5. 5
   过滤filtered
6. 6
   浓缩concentrated under vacuum
7. 7
   其他The crude product was purified by silica gel column chromatography

实验过程

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.

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