Tetrahydrofuran → 2-(N-ethoxymethylanilino)-4-methyl-6-(1-propynyl) pyrimidine

HRID 981484

Reaktionsgleichung

[NH:1]([C:8]1[N:13]=[C:12]([CH3:14])[CH:11]=[C:10]([C:15]#[C:16][CH3:17])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[O:20]1[CH2:24]C[CH2:22][CH2:21]1>CS(C)=O>[CH2:21]([O:20][CH2:24][N:1]([C:8]1[N:13]=[C:12]([CH3:14])[CH:11]=[C:10]([C:15]#[C:16][CH3:17])[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH3:22]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

A solution of 2-anilino-4-methyl-6-(1-propynyl)-pyrimidine (2.5 g) in dimethyl sulfoxide (2.5 ml) were added to a suspension in 50 ml of tetrahydrofuran of 0.5 g of sodium hydride (60%) of which oily component was removed, and the mixture was stirred at 50° C. for 1 hour. After cooling to room temperature, 1.5 g of chloromethyl ethyl ether was added thereto and the resulting mixture was stirred for 5 hours. The reaction mixture was poured into water and extracted with 150 ml of toluene. The toluene layer was washed wit water, dried over magnesium sulfate and concentrated by evaporation under reduced pressure. The rsidue was purified by silica gel column chromatography to obtain 1.6 g (yield: 62%) of 2-(N-ethoxymethylanilino)-4-methyl-6-(1-propynyl) pyrimidine.

Aufarbeitung

customwas removed
temperatureAfter cooling to room temperature
addition1.5 g of chloromethyl ethyl ether was added
stirringthe resulting mixture was stirred for 5 hours
additionThe reaction mixture was poured into water
extractionextracted with 150 ml of toluene
washThe toluene layer was washed wit water
dry with materialdried over magnesium sulfate
concentrationconcentrated by evaporation under reduced pressure
customThe rsidue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-cf1ffae5a76a4e4ca0f2cd1d6f4ff506
Quelldatensatz: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04992438

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