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Potassium Carbonate → {4-[5-(2-Fluoro-phenoxy)-oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethyl-phenoxy}-acetic acid

HRID 81361
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 81361
[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[O:4][C:5]1[N:6]=[CH:7][C:8]2[N:13]=[C:12]([C:14]3[CH:19]=[C:18]([CH3:20])[C:17]([OH:21])=[C:16]([CH3:22])[CH:15]=3)[O:11][C:9]=2[N:10]=1.Br[CH2:28][C:29]([O:31]C(C)(C)C)=[O:30].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[O:4][C:5]1[N:6]=[CH:7][C:8]2[N:13]=[C:12]([C:14]3[CH:15]=[C:16]([CH3:22])[C:17]([O:21][CH2:28][C:29]([OH:31])=[O:30])=[C:18]([CH3:20])[CH:19]=3)[O:11][C:9]=2[N:10]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 1361211154-[5-(2-Fluorophenoxy)oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenol

Produkt 1

HCID 53312125{4-[5-(2-Fluoro-phenoxy)-oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethyl-phenoxy}-acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A suspension of 430 mg of 4-[5-(2-fluoro-phenoxy)-oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethyl-phenol, 0.2 ml of tert-butyl bromoacetate and 423 of mg potassium carbonate in 5 ml of dimethylformamide was stirred at 60° C. for 2 h. After cooling, the solids were removed by filtration and the solvent were distilled off in vacuo. 1.3 ml of trifluoroacetic acid were added to the residue, and the solution was stirred at room temperature for 1 h. Then 10 ml of toluene were added and the solvents were removed in vacuo. The title compound was isolated by silica gel chromatography (heptane/ethyl acetate gradient) as a white solid (135 mg).

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe solids were removed by filtration
  3. distillationthe solvent were distilled off in vacuo
  4. addition1.3 ml of trifluoroacetic acid were added to the residue
  5. stirringthe solution was stirred at room temperature for 1 h
  6. additionThen 10 ml of toluene were added
  7. customthe solvents were removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f4e39e7fc0fd469aaeaed200d4e5014a
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08846690B2

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