Methanol → HCID 178433462, Verbindung

HRID 359683Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 359683
[Cl:1][C:2]1[C:3]([OH:10])=[N:4][C:5]([CH3:9])=[N:6][C:7]=1Cl.[NH2:11][CH2:12][C:13]1[CH:14]=[C:15]([Br:19])[CH:16]=[N:17][CH:18]=1.CO>C(COC)OC>[Br:19][C:15]1[CH:14]=[C:13]([CH2:12][NH:11][C:7]2[NH:6][C:5]([CH3:9])=[N:4][C:3](=[O:10])[C:2]=2[Cl:1])[CH:18]=[N:17][CH:16]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 229922643-(Aminomethyl)-5-bromopyridineHCID 178433461HCID 178433461, Verbindung

Produkt 1

HCID 178433462HCID 178433462, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A stirred mixture of 5,6-dichloro-2-methyl-4-pyrimidinol (1.20 g, 6.70 mmol) and 5-aminomethyl-3-bromopyridine (3.65 g, 19.5 mmol) in dimethoxyethane (25 mL) was heated at reflux for 14 hours. The mixture was then concentrated in vacuo and diluted with water. The precipitate was isolated by filtration with aqueous rinse, recrystallized twice from ethyl acetate, and then recrystallized a third time, but from methanol, to provide the title compound as a pure product (1.07 g, 3.25 mmol, 48%): mp 274°-275° C.; Rf 0.59 (20% MeOH in EtOAc); 1H NMR (DMSO-D6, 400 MHz)δ11.9 (br s, 1H), 8.57 (d, J=2 Hz, 1H), 8.49 (s, 1H), 7.93 (s, 1H), 7.46 (t, J=6 Hz, 1H), 4.56 (d, J=6.1 Hz, 2H), 2.18 (s, 3H); IR (KBr) 3300 (NH), 2790-3000 (CH), 1660, 1615, 2590 (C=C, C=N); mass spectrum m/e 329.8 (M+, 70%), 292.9 (M+ -Cl, 32%).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 14 hours
  3. concentrationThe mixture was then concentrated in vacuo
  4. additiondiluted with water
  5. customThe precipitate was isolated by filtration with aqueous rinse
  6. customrecrystallized twice from ethyl acetate
  7. customrecrystallized a third time

Quellen und Nachweise

ORD-Eintrag
ord-f705fdcdc936417983ac8e441f68d22d
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US05002949

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