反応 #1702110

反応方程式

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

3-aminobenzyl alcohol

p-toluenesulfonic acid monohydrate

→

desired product

収率 98.0%

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

収率 98.0%

溶媒

1,4-dioxane

反応条件

後処理

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

実験手順

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).

出典