4-Fluoroaniline → 5-(3-fluoro-4-hydroxyphenyl)-2-(4-fluorophenylamino)-3-methylpyrimidin-4(3H)-one

HRID 1993348

Reaktionsgleichung

[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10](=[O:18])[N:11]([CH3:17])[C:12](SC)=[N:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[OH:8].[F:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1>Cl.CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10](=[O:18])[N:11]([CH3:17])[C:12]([NH:24][C:23]3[CH:25]=[CH:26][C:20]([F:19])=[CH:21][CH:22]=3)=[N:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[OH:8]

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

5-(3-Fluoro-4-hydroxyphenyl)-3-methyl-2-methylthio-3H-pyrimidin-4-one (Step 5, 0.39 g, 1.5 mmol) was suspended in 3.6 mL p-fluoroaniline and concentrated HCl (1 drop) was added. The reaction was heated in a microwave at 120° C. and 100 W for 10 min (using a Powermax feature on a CEM microwave). The reaction was cooled to RT and diluted with EtOAc (100 mL). The organic phase was extracted with 1 N NaOH (3×15 mL), and the aqueous extracts were neutralized with concentrated HCl. The aqueous layer was extracted with EtOAc (3×20 mL), and the organic extracts were combined, dried over Na2SO4, filtered, and concentrated to give desired compound. MS (ESI pos. ion) m/z: 330. Calc'd for C17H13F2N3O2: 329.10.

Aufarbeitung

temperatureThe reaction was cooled to RT
extractionThe organic phase was extracted with 1 N NaOH (3×15 mL)
extractionThe aqueous layer was extracted with EtOAc (3×20 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-721a86c2602a43f19cb1980402827f2e
Quelldatensatz: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07652009B2

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