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1-[4,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]-6-trimethylsilyl-5-hexyn-1-one → 1-[4,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]-5-hexyn-1-one

HRID 2082032
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2082032
[CH3:1][C:2]([C:5]1[C:10]([OH:11])=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[N:8]=[C:7]([C:16](=[O:26])[CH2:17][CH2:18][CH2:19][C:20]#[C:21][Si](C)(C)C)[N:6]=1)([CH3:4])[CH3:3].O.O.[F-].[K+]>CN(C)C=O>[CH3:4][C:2]([C:5]1[C:10]([OH:11])=[C:9]([C:12]([CH3:13])([CH3:14])[CH3:15])[N:8]=[C:7]([C:16](=[O:26])[CH2:17][CH2:18][CH2:19][C:20]#[CH:21])[N:6]=1)([CH3:1])[CH3:3]
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Komponenten

4

Edukt 2

HCID 104520651-[4,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]-6-trimethylsilyl-5-hexyn-1-oneHCID 23708904Potassium fluoride dihydrate

Produkt 1

HCID 104026731-[4,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]-5-hexyn-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 1-[4,6-bis(1,1-dimethylethyl)-5-hydroxypyrimidin-2-yl]-6-trimethylsilyl-5-hexyn-1-one (0.87 g, 2.3 mmol), Example 8, and potassium fluoride dihydrate (0.91 g, 9.7 mmol) in N,N-dimethylformamide (12 mL) is warmed to 50° C. After stirring for 47 hours at 50° C., the solvent is removed under vacuum and the organic residue is diluted with water. This mixture is extracted with ethyl acetate and the combined extracts are washed with saturated aqueous ammonium chloride solution and brine. The organic is concentrated under vacuum and the organic residue purified by flash chromatorgraphy (SiO2, 20% ethyl acetate (hexane) followed by recrystallization from methanol and water to give 0.48 g (68%) of the title compound), mp 64°-66° C.

Aufarbeitung

  1. customthe solvent is removed under vacuum
  2. additionthe organic residue is diluted with water
  3. extractionThis mixture is extracted with ethyl acetate
  4. washthe combined extracts are washed with saturated aqueous ammonium chloride solution and brine
  5. concentrationThe organic is concentrated under vacuum
  6. customthe organic residue purified by flash chromatorgraphy (SiO2, 20% ethyl acetate (hexane) followed by recrystallization from methanol and water to give 0.48 g (68%) of the title compound), mp 64°-66° C.

Quellen und Nachweise

ORD-Eintrag
ord-0d36db042726453b98e1b22d12424a22
Quelldatensatz
uspto-grants-1993_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05187175

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