Dimethylformamide → (3,5-Dichloro-phenyl)-(5-ethyl-2,6-dimethoxy-pyrimidin-4-yl)-methanone

Reaktionsgleichung

[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([C:12]2[C:17]([CH2:18][CH3:19])=[C:16]([O:20][CH3:21])[N:15]=[C:14]([O:22][CH3:23])[N:13]=2)C#N)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[H-].[Na+].CN(C=[O:30])C>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:12]2[C:17]([CH2:18][CH3:19])=[C:16]([O:20][CH3:21])[N:15]=[C:14]([O:22][CH3:23])[N:13]=2)=[O:30])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Komponenten

Edukt 3

HCID 6228Dimethylformamide

HCID 24758Sodium hydride

HCID 59184717HCID 59184717, Verbindung

Produkt 1

HCID 59184701(3,5-Dichloro-phenyl)-(5-ethyl-2,6-dimethoxy-pyrimidin-4-yl)-methanoneAusbeute 72 %

Versuchsvorschrift

To a stirred solution of (62) (1.97 g, 5.59 mmol) in anhydrous DMF (25 ml) under nitrogen atmosphere, was added 60% sodium hydride (224 mg, 5.59 mmol). After 10 min., oxygen was bubbled into the reaction mixture for 4 hr. The mixture was partitioned between ether and aqueous saturated ammonium chloride solution. The organic layer was taken, washed with water twice, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was then purified by silica gel column chromatography (eluent, ether:hexanes (1:30)) to afford 1.37 g (72%) of the title compound as a white solid. m.p. 118-119° C.; 1H NMR (200 MHz, CDCl3) δ 1.09 (3H, t, J=7.4 Hz), 2.46 (2H, q, J=7.4 Hz), 3.95 (3H, s), 4.08 (3H, s), 7.58 (1H, t, J=1.8 Hz), 7.56 (2H, d, J=1.8 Hz).