Reaktion #46604

ord-03e5bbc4997841908c5f88cf5a5ca788

Reaktionsgleichung

Nc1ncc(Br)cn1
2-amino-5-bromopyrimidine
C=CC(=O)N(C)Cc1cn(C)c2ncccc12
N-methyl-N-(1-methyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)acrylamide
Cc1ccccc1P(c1ccccc1C)c1ccccc1C
P(o-tolyl)3
CCN(C(C)C)C(C)C
(i-Pr)2NEt
→
CN(Cc1cn(C)c2ncccc12)C(=O)/C=C/c1cnc(N)nc1
title compound
Ausbeute 20.0%
CN(Cc1cn(C)c2ncccc12)C(=O)/C=C/c1cnc(N)nc1
(E)-3-(2-aminopyrimidin-5-yl)-N-methyl-N-(1-methyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)acrylamide
Ausbeute 20.0%

Edukte

Nc1ncc(Br)cn1
2-amino-5-bromopyrimidine
C=CC(=O)N(C)Cc1cn(C)c2ncccc12
N-methyl-N-(1-methyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)acrylamide
Cc1ccccc1P(c1ccccc1C)c1ccccc1C
P(o-tolyl)3
CCN(C(C)C)C(C)C
(i-Pr)2NEt

Reagenzien

CC(=O)[O-].CC(=O)[O-].[Pd+2]
Pd(OAc)2

Lösungsmittel

CCC#N
propionitrile

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturthen heated to reflux
  2. 2
    Einengenconcentrated

Vorschrift

A solution of 2-amino-5-bromopyrimidine (0.27 g, 1.55 mmole), N-methyl-N-(1-methyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)acrylamide (0.5 g, 2.33 mmole), Pd(OAc)2 (0.037 g, 0.163 mmole), P(o-tolyl)3 (0.085 g, 0.28 mmole), and (i-Pr)2NEt (0.42 mL, 2.33 mmole) in propionitrile (20 mL) was degassed then heated to reflux. After 18 hr the mixture was cooled to RT and concentrated. Flash chromatography on silica gel (10% MeOH/CH2Cl2) gave the title compound (0.100 g, 18%): MS (ES) m/e 363 (M+H)+.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07741339B2uspto-grants-2010_06