N,N-二甲基甲酰胺 → 4-Chloro-3-(5-isopropyl-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-benzonitrile

反应方程式

Cl[C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[C:6]([O:11][CH3:12])[N:5]=[C:4]([O:13][CH3:14])[N:3]=1.[Cl:15][C:16]1[C:23]([CH3:24])=[CH:22][C:19]([C:20]#[N:21])=[CH:18][C:17]=1[CH2:25]C#N.[H-].[Na+].CN(C=[O:34])C>>[Cl:15][C:16]1[C:23]([CH3:24])=[CH:22][C:19]([C:20]#[N:21])=[CH:18][C:17]=1[C:25]([C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[C:6]([O:11][CH3:12])[N:5]=[C:4]([O:13][CH3:14])[N:3]=1)=[O:34]

参与物

反应物 4

HCID 6228N,N-二甲基甲酰胺

HCID 24758氢化钠

HCID 160881864-氯-5-异丙基-2,6-二甲氧基嘧啶

HCID 670504934-Chloro-3-cyanomethyl-5-methyl-benzonitrile

产物 1

HCID 582034604-Chloro-3-(5-isopropyl-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-benzonitrile收率 11%

实验过程

To a solution of 4-chloro-5-isopropyl-2,6-dimethoxy-pyrimidine (0.442 g, 2.04 mmol) and 4-chloro-3-cyanomethyl-5-methyl-benzonitrile (0.3707 g, 1.94 mmol) in DMF at 0° C. was added NaH portionwise over 15 minutes to give an orange-red reaction mixture. After stirring for 24 hr, O2 was bubbled into the reaction mixture for 36 hr. The reaction mixture was quenched with saturated ammonium chloride solution and methanol, and diluted with ethyl acetate. The organic layer was washed with saturated ammonium chloride solution, H2O, saturated ammonium chloride solution and dried (MgSO4), then concentrated and purified by flash column chromatography (silica gel, 5 to 50% ethyl acetate/hexane) to give title compound (0.0767 g, 11%). 1H NMR (300 MHz, CDCl3): 7.67 (s, 1H), 7.59 (s, 1H), 4.00 (s, 3H), 3.75 (s, 3H), 3.3-3.2 (m, 1H), 2.37 (s, 3H), 1.25 (s, 3H), 1.23 (s, 3H); 13C NMR (75 MHz, CDCl3): 192.8, 171.1, 162.2, 160.2, 139.1, 138.9, 137.3, 135.9, 132.3, 119.9, 117.4, 110.8, 54.7, 54.2, 26.5, 20.2, 20.2; Mass Spectrum: 360.2, 362.1 (M+H).