Reaktion #418023

ord-5ebc3882721e4d1aac7410a2df8c0f3b

Reaktionsgleichung

OCCF
2-fluoro-ethanol
CCNC(=O)C(C)c1ccc(C#Cc2cnc(Cl)nc2)cc1
2-[4-(2-chloro-pyrimidin-5-ylethynyl)-phenyl]-N-ethyl-propionamide
[H-].[Na+]
sodium hydride
CCNC(=O)C(C)c1ccc(C#Cc2cnc(OCCF)nc2)cc1
desired product
CCNC(=O)C(C)c1ccc(C#Cc2cnc(OCCF)nc2)cc1
N-Ethyl-2-{4-[2-(2-fluoro-ethoxy)-pyrimidin-5-ylethynyl]-phenyl}-propionamide

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeAfter that time, the solvent is evaporated
  2. 2
    Sonstigethe residue s purified by HPLC (preparative column: Sunfire, eluent A: water+0.1% TFA, eluent B: MeOH)

Vorschrift

To 13 mg (0.21 mmol) 2-fluoro-ethanol in 0.5 mL 1,4-dioxane are added 34 mg (0.10 mmol) 2-[4-(2-chloro-pyrimidin-5-ylethynyl)-phenyl]-N-ethyl-propionamide (XVIII.1) in 1 mL 1,4-dioxane, followed by 12 mg (0.30 mmol) sodium hydride (60% in mineral oil). The mixture is stirred at rt for 12 h. After that time, the solvent is evaporated and the residue s purified by HPLC (preparative column: Sunfire, eluent A: water+0.1% TFA, eluent B: MeOH) to yield the desired product.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08877754B2uspto-grants-2014_11