反应 #1702110

反应方程式

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

3-aminobenzyl alcohol

p-toluenesulfonic acid monohydrate

→

desired product

收率 98.0%

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

收率 98.0%

溶剂

1,4-dioxane

反应条件

后处理

1. 1
   温度was heated at 70° C. overnight
2. 2
   其他The reaction was quenched with NaHCO3 (saturated)
3. 3
   其他The organic solvent was removed under vacuum
4. 4
   workup.ADDITIONfollowed by the addition of water and EtOAc
5. 5
   萃取The aqueous layer was extracted with EtOAc twice
6. 6
   干燥dried over Na2SO4
7. 7
   浓缩concentrated under vacuum

实验过程

Into the reaction flask was added 2,5-dichloro-N-(3-methoxybenzyl)pyrimidin-4-amine (0.82 g, 2.9 mmol), 1,4-dioxane (20 mL), 3-aminobenzyl alcohol (0.53 g, 4.3 mmol), and p-toluenesulfonic acid monohydrate (0.22 g, 1.2 mmol). The mixture was heated at 105° C. for 3 hours and then was heated at 70° C. overnight. The reaction was quenched with NaHCO3 (saturated). The organic solvent was removed under vacuum, followed by the addition of water and EtOAc. The aqueous layer was extracted with EtOAc twice. The organic layers were combined, dried over Na2SO4 and concentrated under vacuum to give the desired product as a brown powder (1.05 g, 98%). LCMS for C19H20N4O2 (M+H)+: m/z=371.1, 373.0. 1H NMR (400 MHz, DMSO-d6): δ 9.54 (s, 1H), 8.28 (s, 1H), 8.03 (s, 1H), 7.54 (s, 1H), 7.40 (d, J=8.3 Hz, 1H), 7.20 (t, J=8.3 Hz, 1H), 7.14 (t, J=7.9 Hz, 1H), 6.89 (m, 1H), 6.77 (ddd, J=8.3, 2.2, 1.4 Hz, 1H), 4.59 (d, J=6.2 Hz, 2H), 4.38 (s, 2H), 3.64 (s, 3H).

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