Reaktion #46588

Reaktionsgleichung

N-methyl-N-(2-methyl-1H-indol-3-ylmethyl)acrylamide

2-amino-5-bromopyrimidine

tri-ortho-tolylphosphine

diisopropylethylamine

→

title compound

Ausbeute 128.8%

(E)-3-(2-Aminopyrimidin-5-yl)-N-(2-methyl-1H-indol-3-ylmethyl)-N-methylacrylamide

Ausbeute 128.8%

Lösungsmittel

propionitrile

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux overnight
2. 2
   FiltrationThe dark mixture was filtered through Celite®
3. 3
   Einengenthe filtrate was concentrated

Vorschrift

A solution of N-methyl-N-(2-methyl-1H-indol-3-ylmethyl)acrylamide (1.18 g, 6.5 mmole), 2-amino-5-bromopyrimidine (0.5 g, 2.9 mmole), Pd(OAc)2 (0.11 g, 0.49 mmole), tri-ortho-tolylphosphine (0.17 g, 0.55 mmole), and diisopropylethylamine (1.5 mL, 8.6 mmole) in propionitrile (100 mL) and DMF (10 mL) was heated at reflux overnight. The dark mixture was filtered through Celite®, and the filtrate was concentrated. Flash chromatography on silica gel (9:1 CHCl3/CH3OH containing 5% NH4OH) gave the title compound (1.2 g, 65%): MS (ES) m/e 372 (M+H)+.

Quelle