반응 #1702110

반응 방정식

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

3-aminobenzyl alcohol

p-toluenesulfonic acid monohydrate

→

desired product

수율 98.0%

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

수율 98.0%

용매

1,4-dioxane

반응 조건

후처리

1. 1
   온도was heated at 70° C. overnight
2. 2
   기타The reaction was quenched with NaHCO3 (saturated)
3. 3
   기타The organic solvent was removed under vacuum
4. 4
   workup.ADDITIONfollowed by the addition of water and EtOAc
5. 5
   추출The aqueous layer was extracted with EtOAc twice
6. 6
   건조dried over Na2SO4
7. 7
   농축concentrated under vacuum

실험 절차

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).

출처