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

Reaction equation

[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

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 24758Sodium hydride

HCID 59184717HCID 59184717, compound

Product 1

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

Procedure

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).