Reacción #46588

Ecuación de reacción

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

2-amino-5-bromopyrimidine

tri-ortho-tolylphosphine

diisopropylethylamine

→

title compound

Rendimiento 128.8%

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

Rendimiento 128.8%

Disolventes

propionitrile

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux overnight
2. 2
   FiltraciónThe dark mixture was filtered through Celite®
3. 3
   Concentraciónthe filtrate was concentrated

Procedimiento

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)+.

Fuente