Реакция #46588

Уравнение реакции

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

2-amino-5-bromopyrimidine

tri-ortho-tolylphosphine

diisopropylethylamine

→

title compound

Выход 128.8%

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

Выход 128.8%

Растворители

propionitrile

DMF

Условия реакции

Обработка

1. 1
   Температураat reflux overnight
2. 2
   ФильтрацияThe dark mixture was filtered through Celite®
3. 3
   Концентрированиеthe filtrate was concentrated

Методика

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)+.

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