Dimethylformamide → HCID 59853046, Verbindung

HRID 2237177Notizen

Reaktionsgleichung

[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[F:9][C:10]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:11]=1[OH:19].C([O-])([O-])=O.[K+].[K+].CN(C=O)C>C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[N:7]=[C:6]([O:19][C:11]2[CH:12]=[CH:13][C:14]([N+:16]([O-:18])=[O:17])=[CH:15][C:10]=2[F:9])[CH:5]=[CH:4][N:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A mixture of 2,4-dichloropyrimidine (Aldrich, 0.74 g, 5.0 mmol), 2-fluoro-4-nitrophenol (Avacado, 0.79 g, 5.0 mmol), K2CO3 (0.76 g, 5.5 mmol), and DMF (50 mL) was heated at 100° C. for 2 h. The mixture was cooled and diluted with saturated NaHCO3 solution (100 mL) and extracted with EtOAc. The EtOAc extract was washed with brine, dried (MgSO4) and concentrated in vacuo to give a mixture of the 2-phenoxy- and 4-phenoxypyrimidine regioisomers as a yellow solid. The regioisomers were separated by flash chromatography using 10-40% EtOAc in hexanes as the eluent to give the title compound (0.71 g, 53%) as a white solid. 1H NMR (DMSO-d6) δ 8.76 (dd, 1H, J=6.0, 1.6 Hz), 8.43 (dt, 1H, J=9.8, 2.2 Hz), 8.23 (dd, 1H, J=8.8, 1.6 Hz), 7.80 (dt, 1H, J=9.8, 2.2 Hz), 7.48 (dd, 1H, J=6.0, 2.2 Hz).

Aufarbeitung

temperatureThe mixture was cooled
extractionextracted with EtOAc
extractionThe EtOAc extract
washwas washed with brine
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customto give
customThe regioisomers were separated by flash chromatography

Quellen und Nachweise

ORD-Eintrag: ord-b79b9064f63144c69a5c040e24cc2c83
Quelldatensatz: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07714138B2

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