2,6-Dimethylbenzoyl chloride → N'-[1-(2,6-dimethylbenzoyl)-5-fluoro-2-oxo-1,2-dihydro-pyrimidin-4-yl]-N,N-dimethylformamidine

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Reaktionsgleichung

[F:1][C:2]1[C:3]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])=[N:4][C:5]([OH:8])=[N:6][CH:7]=1.[CH3:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:16]=1[C:17](Cl)=[O:18]>N1C=CC=CC=1>[CH3:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:16]=1[C:17]([N:6]1[CH:7]=[C:2]([F:1])[C:3]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])=[N:4][C:5]1=[O:8])=[O:18]

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

To an 8 mL screw-cap vial were added pyridine (2 mL), N′-(5-fluoro-2-hydroxy-pyrimidin-4-yl)-N,N-dimethylformamidine (100 mg, 0.54 mmol), and 2,6-dimethylbenzoyl chloride (102 mg, 0.60 mmol). The mixture was heated to 40° C. for 2 h, evaporated to dryness, and partitioned between ethyl acetate (EtOAc) and water (H2O). The organic phase was dried over magnesium sulfate (MgSO4), filtered, evaporated, and the residue was purified by reverse phase chromatography to yield the title compound as a white solid (63 mg, 37%): mp 120-150° C.; 1H NMR (300 MHz, CDCl3) δ 8.81 (s, 1H), 8.22 (d, J=6.04 Hz, 1H), 7.23-7.17 (m, 1H), 7.07-7.01 (m, 2H), 3.27 (s, 3H), 3.24 (s, 3H), 2.24 (s, 6H); ESIMS m/z 317 ([M+H]+).

Aufarbeitung

customTo an 8 mL screw-cap vial
customevaporated to dryness
custompartitioned between ethyl acetate (EtOAc) and water (H2O)
dry with materialThe organic phase was dried over magnesium sulfate (MgSO4)
filtrationfiltered
customevaporated
customthe residue was purified by reverse phase chromatography

Quellen und Nachweise

ORD-Eintrag: ord-8925733bb8854706b102058df8f5f1e6
Quelldatensatz: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08470839B2

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