Trimethylsilyl cyanide → 2-(3-Hydroxypropoxy)-2-(2-methylpyrimidin-5-yl)acetonitrile

反応式

[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:8]=[N:9][C:10]([CH3:13])=[N:11][CH:12]=1.C[Si]([C:18]#[N:19])(C)C>C(Cl)Cl.[I-].[Zn+2].[I-]>[OH:1][CH2:6][CH2:5][CH2:4][O:3][CH:2]([C:7]1[CH:8]=[N:9][C:10]([CH3:13])=[N:11][CH:12]=1)[C:18]#[N:19]

参加物

実験手順

To an ice-cold solution of 5-(1,3-dioxan-2-yl)-2-methylpyrimidine (140 mg, 0.78 mmol) in DCM (5.0 ml) was added zinc iodide (124 mg, 0.39 mmol). Trimethylsilyl cyanide (116 mg, 0.155 ml, 1.17 mmol) was added dropwise over a period of 10 minutes. Cooling was removed and the reaction was stirred for 40 hours at room temperature. The mixture was poured into H2O (20 mL) and extracted with DCM (3×20 mL), the combined org. phases were washed with brine, dried over MgSO4 and concetrated in vacuo. The crude product was used for next step without further purification.