Dimethylformamide → (3-Chloro-5-methyl-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-methanone

반응식

[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([C:12]2[C:17]([CH:18]([CH3:20])[CH3:19])=[C:16]([O:21][CH3:22])[N:15]=[C:14]([O:23][CH3:24])[N:13]=2)C#N)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[H-].[Na+].CN(C=[O:31])C>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:12]2[C:17]([CH:18]([CH3:20])[CH3:19])=[C:16]([O:21][CH3:22])[N:15]=[C:14]([O:23][CH3:24])[N:13]=2)=[O:31])[CH:5]=[C:6]([CH3:8])[CH:7]=1

참가 물질

반응물 3

HCID 6228Dimethylformamide

HCID 24758Sodium hydride

HCID 59184692(3-Chloro-5-methyl-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-acetonitrile

생성물 1

HCID 59184800(3-Chloro-5-methyl-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-methanone수율 80%

실험 절차

To a stirred solution of (48) (7.56 g, 21.88 mmol) in anhydrous DMF (100 ml) in a water bath under an atmosphere of nitrogen, was portionwise added 60% sodium hydride (1.05 g, 26 mmol). After 30 min, oxygen gas was bubbled into the reaction mixture for 4 hr. The mixture was neutralized with aqueous saturated ammonium chloride solution. The crude product was extracted with ether and purified by silica gel column chromatography (eluent, ether:hexane (1:4)) to afford 5.87 g (80%) of a white solid. m.p. 119-120° C.; 1H NMR (200 MHz, CDCl3) δ: 1.19 (6H, d, J=7.1 Hz), 2.38 (3H, s), 2.80 (1H, m), 3.93 (3H, s), 4.06 (3H, s), 7.40-7.61 (3H, m).