Acetonitrile → ethyl 1-(2-chloro-5-fluoropyrimidin-4-yl)-3-methyl-1H-pyrazole-4-carboxylate

HRID 539891

Reaktionsgleichung

[CH3:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][NH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:18][C:19]1[N:24]=C(Cl)[C:22]([F:26])=[CH:21][N:20]=1.C(#[N:29])C>C(OCC)(=O)C>[Cl:18][C:19]1[N:24]=[C:3]([N:4]2[CH:5]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:2]([CH3:1])=[N:29]2)[C:22]([F:26])=[CH:21][N:20]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a solution of ethyl 3-methyl-1H-pyrrole-4-carboxylate (3.15 g, 20.5 mmol) in acetonitrile (MeCN) were added potassium carbonate (5.7 g, 41 mmol) and 2,4-dichloro-5-fluoropyrimidine (3.4 g, 20.5 mmol) at room temperature. The resulting slurry was heated at 80° C. for 3 hours with monitoring a reaction with LC-MS or thin layer chromatography (TLC). It was diluted with ethyl acetate and washed with brine. The collected organic layer was dried over anhydrous sodium sulfate and then partially concentrated in vacuo. To this, n-hexanes were added to form pale yellow precipitates. The resulting solids were collected by filtration and rinsed with n-hexanes and then dried under high vacuum to give 4.9 g (85%) of the target intermediate 3; MS (ESI) m/z 285 [M+H]+

Aufarbeitung

customa reaction with LC-MS or thin layer chromatography (TLC)
washwashed with brine
dry with materialThe collected organic layer was dried over anhydrous sodium sulfate
concentrationpartially concentrated in vacuo
additionTo this, n-hexanes were added
customto form pale yellow precipitates
filtrationThe resulting solids were collected by filtration
washrinsed with n-hexanes
customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag: ord-2857bc4ecf8a41a8893758f890bd6447
Quelldatensatz: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08871778B2

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