4-Chloro-2-(methylsulfanyl)-6-(trifluoromethyl)pyrimidine → N-(3-methoxy-1H-pyrazol-5-yl)-2-(methylthio)-6-(trifluoromethyl)pyrimidin-4-amine

HRID 415444

Reaktionsgleichung

Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([S:12][CH3:13])[N:3]=1.Cl.[CH3:15][O:16][C:17]1[NH:21][N:20]=[C:19]([NH2:22])[CH:18]=1>C(O)C>[CH3:15][O:16][C:17]1[CH:18]=[C:19]([NH:22][C:2]2[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([S:12][CH3:13])[N:3]=2)[NH:20][N:21]=1

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

To a solution of 4-chloro-2-(methylthio)-6-(trifluoromethyl)pyrimidine (2.29 g) in absolute ethanol (50 mL) was added DIEPA (4.4 mL) and 5-methoxy-1H-pyrazol-3-amine hydrogen chloride salt (1.46 g). The resulting solution was heated at 90° C. for over night. The solvent was evaporated under reduced pressure. The crude compound was purified by Gilson (10-60% MeCN/H2O, 15 minutes) to give N-(3-methoxy-1H-pyrazol-5-yl)-2-(methylthio)-6-(trifluoromethyl)pyrimidin-4-amine as solid (0.64 g). m/z 306. N-(3-methoxy-1H-pyrazol-5-yl)-2-(methylthio)-6-(trifluoromethyl)pyrimidin-4-amine (240 mg) was dissolved in methylene chloride (5 mL), MCPBA (529 mg) was added. The resulting solution was stirred at room temperature for 0.5 hours and separate between methylene chloride and saturated sodium carbonate water solution. The organic layer was dried and solvent was removed under reduced pressure and low temperature. The crude product (270 mg) was carried on to do next step without further purification. m/z 338.

Aufarbeitung

customThe solvent was evaporated under reduced pressure
customThe crude compound was purified by Gilson (10-60% MeCN/H2O, 15 minutes)

Quellen und Nachweise

ORD-Eintrag: ord-a3834143e34d4281a1cb9762b51be000
Quelldatensatz: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08088784B2

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