Cesium carbonate → N-(1-(4-((4-(Pyrimidin-5-yloxy)phenyl)ethynyl)phenyl)propan-2-yl)acetamide

HRID 76189

Reaktionsgleichung

Reaktionsgleichung von HRID 76189
I[C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1.[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[C:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH:24]([NH:26][C:27](=[O:29])[CH3:28])[CH3:25])=[CH:19][CH:18]=2)=[CH:11][CH:10]=1.Cl.CN(C)CC(O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>[Cu]I.O1CCOCC1>[N:4]1[CH:3]=[C:2]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]#[C:16][C:17]3[CH:22]=[CH:21][C:20]([CH2:23][CH:24]([NH:26][C:27](=[O:29])[CH3:28])[CH3:25])=[CH:19][CH:18]=3)=[CH:11][CH:10]=2)[CH:7]=[N:6][CH:5]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 75605N,N-Dimethylglycine hydrochlorideHCID 12014215-IodopyrimidineHCID 66610715N-(1-(4-((4-hydroxyphenyl)ethynyl)phenyl)propan-2-yl)acetamide

Produkt 1

HCID 66635455N-(1-(4-((4-(Pyrimidin-5-yloxy)phenyl)ethynyl)phenyl)propan-2-yl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

28.1 mg (0.14 mmol) 5-iodopyrimidine, 40.0 mg (0.14 mmol) N-(1-(4-((4-hydroxy-phenyl)ethynyl)phenyl)propan-2-yl)acetamide (I76.1), 1.30 mg (0.07 mmol) CuI, 1.9 mg (0.14 mmol) N,N-dimethylglycine hydrochloride and 58.7 mg (0.18 mmol) Cs2CO3 are added to 1 mL dioxane. The reaction mixture is stirred at 90° C. for 2 h then filtered through a plug of silica gel and washed with DMF. The filtrate is purified by HPLC (MeOH/H2O/TFA).

Aufarbeitung

  1. filtrationthen filtered through a plug of silica gel
  2. washwashed with DMF
  3. customThe filtrate is purified by HPLC (MeOH/H2O/TFA)

Quellen und Nachweise

ORD-Eintrag
ord-3e1a1fdc1d1546e5b2efb470e5ef9a12
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835472B2

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