Diisopropylamine → 2-[2-(Methylthio)pyrimidin-4-yl]-1-[3-(trifluoromethyl)phenyl]ethanone

HRID 342686

Reaktionsgleichung

C(NC(C)C)(C)C.[Li+].CCC[CH2-].[CH3:13][S:14][C:15]1[N:20]=[C:19]([CH3:21])[CH:18]=[CH:17][N:16]=1.CON(C)[C:25](=[O:36])[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=1>C1COCC1>[CH3:13][S:14][C:15]1[N:20]=[C:19]([CH2:21][C:25]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:33])([F:34])[F:35])[CH:27]=2)=[O:36])[CH:18]=[CH:17][N:16]=1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

To a solution of diisopropylamine (7.9 mL, 0.056 mole) in THF (100 mL) at -78° C. under argon was added 2.5M N-butyllithium (22.5 mL, 0.056 mole), followed after 5 minutes by a solution of 2-methylthio-4-methylpyrimidine (5.27 g, 0.0376 mole) in THF (20 mL). Upon stirring for 15 min. at -78° C., a solution of N-methoxy-N-methyl-3-trifluoromethylbenzamide (9.63 g, 0.041 mole) in THF (90 mL) was added. The reaction was allowed to warm to 0° C. and then quenched by pouring into water (400 mL) and ethyl acetate (400 mL). The layers were separated and the aqueous layer washed with ethyl acetate (200 mL). The ethyl acetate extracts were combined, dried over anhydrous sodium sulfate, filtered, and concentrated to a solid (11.9 g). Trituration with 10% ether/hexane (100 mL) gave 9.5 g of the title compound.

Aufarbeitung

temperatureto warm to 0° C.
customquenched
additionby pouring into water (400 mL) and ethyl acetate (400 mL)
customThe layers were separated
washthe aqueous layer washed with ethyl acetate (200 mL)
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated to a solid (11.9 g)

Quellen und Nachweise

ORD-Eintrag: ord-8a0841ce34fc46729fd7904e7cbb30b5
Quelldatensatz: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05859041

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