Hydrochloric Acid → HCID 67257923, Verbindung

HRID 2359017Notizen

Reaktionsgleichung

[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.[Cl:10][C:11]1[S:15][C:14]([C:16](OCC)=[O:17])=[CH:13][CH:12]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl>C1COCC1>[Cl:10][C:11]1[S:15][C:14]([C:16](=[O:17])[CH2:1][C:2]2[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=2)=[CH:13][CH:12]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of 4-methyl-2-(methylsulfanyl)pyrimidine (1 eq, 235 mmol) and ethyl 5-chlorothiophene-2-carboxylate (1.11 eq, 261 mmol) in anhydrous THF (400 mL) at 0° C., under N2 was added dropwise a solution of lithium bis(trimethylsilyl)amide (1M solution in hexanes, 1.6 eq, 376 mmol). The resulting mixture was stirred for 3 h at 0° C. and then stirred at room temperature overnight. A solution of HCl 1M (750 mL) was then added till pH=1. The aqueous layer was extracted with ethyl acetate and the combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The residue was diluted with diisopropylether and the resulting precipitate was filtered and to afford 29.5 g (43% yield) of 1-(5-chloro-2-thienyl)-2-[2-(methylsulfanyl)pyrimidin-4-yl]ethanone.

Aufarbeitung

stirringstirred at room temperature overnight
extractionThe aqueous layer was extracted with ethyl acetate
washthe combined organic extracts were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
additionThe residue was diluted with diisopropylether
filtrationthe resulting precipitate was filtered

Quellen und Nachweise

ORD-Eintrag: ord-216352ca6f2f46a3b9e3bbc754c898d2
Quelldatensatz: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08685974B2

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