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

HRID 2082033
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2082033
[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](N(OC)C)=[O:17])[N:6]=1)([CH3:4])[CH3:3].[CH3:22][Si:23]([CH3:32])([CH3:31])[C:24]#[C:25][CH2:26][CH2:27][CH2:28][Mg]Br>O1CCCC1>[CH3:15][C:12]([C:9]1[C:10]([OH:11])=[C:5]([C:2]([CH3:3])([CH3:1])[CH3:4])[N:6]=[C:7]([C:16](=[O:17])[CH2:28][CH2:27][CH2:26][C:25]#[C:24][Si:23]([CH3:32])([CH3:31])[CH3:22])[N:8]=1)([CH3:13])[CH3:14]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 100401704,6-Bis(1,1-dimethylethyl)-5-hydroxy-N-methoxy-N-methyl-2-pyrimidinecarboxamideHCID 178504199HCID 178504199, Verbindung

Produkt 1

HCID 104520651-[4,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]-6-trimethylsilyl-5-hexyn-1-oneAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4,6-bis(1,1-dimethylethyl)-5-hydroxy-N-methoxy-N-methyl-2-pyrimidinecarboxamide (1,00 g, 3.38 mmols) in tetrahydrofuran (50 mL) under nitrogen atmosphere is added a freshly prepared 0.105M solution of 5-trimethylsilylpent-4-ynyl magnesium bromide (81 mL, 8.5 mmols) [from 5-bromo-1-trimethylsilyl-1pentyne (3.86 g, 17.5 mmol) and magnesium (1.50 g, 61.7 mg-atom) in tetrahydrofuran (140 mL)] dropwise. After stirring 16 hours, the resulting mixture is quenched with saturated aqueous ammonium chloride solution and extracted with ethyl ether. The combined extracts are washed with brine and the organic phase is dried over magnesium sulfate. Concentration under vacuum is followed by purification of the organic residue by flash chromatography (SiO2, 20% ethyl acetate/hexane) to give 0.97 g (77%) of the title compound which is used without further purification to make the compound of Example 7.

Aufarbeitung

  1. customthe resulting mixture is quenched with saturated aqueous ammonium chloride solution
  2. extractionextracted with ethyl ether
  3. washThe combined extracts are washed with brine
  4. dry with materialthe organic phase is dried over magnesium sulfate
  5. concentrationConcentration under vacuum
  6. customis followed by purification of the organic residue by flash chromatography (SiO2, 20% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-e6552dc7ec2d471d8e3285bc67fc7e63
Quelldatensatz
uspto-grants-1993_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05187175

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