Diethyl Ether → 1-[2-(Methylsulfanyl)pyrimidin-4-yl]ethan-1-one

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Reaktionsgleichung

C[Mg]Br.C([O:6][CH2:7][CH3:8])C.CON(C)C([C:14]1[CH:19]=[CH:18][N:17]=[C:16]([S:20][CH3:21])[N:15]=1)=O>C1COCC1>[CH3:21][S:20][C:16]1[N:17]=[C:18]([C:7](=[O:6])[CH3:8])[CH:19]=[CH:14][N:15]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A solution of methylmagnesium bromide in diethyl ether (3.0 M, 6.10 mL, 18.3 mmol, 3.0 equiv) was added to a solution of N-methoxy-N-methyl-2-(methylthio)pyrimidine-4-carboxamide (1-2, 1.30 g, 6.10 mmol, 1 equiv) in THF at −78° C. The reaction mixture was warmed to 0° C., stirred for 30 minutes, then partitioned between brine and ethyl acetate (2×75 mL). The combined organic layers were dried over sodium sulfate and concentrated to give 1-[2-(methylthio)pyrimidin-4-yl]ethanone (1-3) as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 8.74 (d, 1H, J=4.9 Hz), 7.51 (d, 1H, J=4.9 Hz), 2.70 (s, 3H), 2.63 (s, 3H).

Aufarbeitung

custompartitioned between brine and ethyl acetate (2×75 mL)
dry with materialThe combined organic layers were dried over sodium sulfate
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-998f5eacf3b541eebbb0a317790ca708
Quelldatensatz: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07109204B2

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