Reaktion #73149

ord-e874ca1e46cf4541a964dd6985c93daa

Reaktionsgleichung

CC[C@@H]1C(=O)N(C)c2cnc(Cl)nc2N1C1CCCC1
Intermediate B
CC[C@@H]1C(=O)N(C)c2cnc(Cl)nc2N1C1CCCC1
(R)-2-Chloro-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one
C#Cc1ccccc1
ethynylbenzene
CCN(CC)CC
Et3N
→
CC[C@@H]1C(=O)N(C)c2cnc(C#Cc3ccccc3)nc2N1C1CCCC1
(R)-8-cyclopentyl-7-ethyl-5-methyl-2-(phenylethynyl)-7,8-dihydropteridin-6(5H)-one

Edukte

CC[C@@H]1C(=O)N(C)c2cnc(Cl)nc2N1C1CCCC1
Intermediate B
CC[C@@H]1C(=O)N(C)c2cnc(Cl)nc2N1C1CCCC1
(R)-2-Chloro-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one
C#Cc1ccccc1
ethynylbenzene
CCN(CC)CC
Et3N

Reagenzien

[Cl][Pd]([Cl])([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1
Pd(PPh3)2Cl2
[Cu][I]
CuI

Lösungsmittel

CN(C)C=O
DMF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturThe mixture was refluxed for 18 h under argon
  2. 2
    Extraktionextracted with EtOAc
  3. 3
    Sonstigepurified by silica gel column

Vorschrift

To a solution of Intermediate B (1.0 eq) in DMF, ethynylbenzene (compound III-139, 3.0 eq), Pd(PPh3)2Cl2 (0.2 eq), CuI (0.25 eq) and Et3N (5.0 eq) were added. The mixture was refluxed for 18 h under argon, extracted with EtOAc and purified by silica gel column to give (R)-8-cyclopentyl-7-ethyl-5-methyl-2-(phenylethynyl)-7,8-dihydropteridin-6(5H)-one (compound IV-139).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08541418B2uspto-grants-2013_09