Reaktion #1702110

Reaktionsgleichung

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

3-aminobenzyl alcohol

p-toluenesulfonic acid monohydrate

→

desired product

Ausbeute 98.0%

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

Ausbeute 98.0%

Lösungsmittel

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle