[BH4-].[Li+].C[Si](C)(C)Cl.[C:8]1([N:14]2[C:18]([CH2:19][C:20]#[N:21])=[N:17][C:16]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:15]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[C:8]1([N:14]2[C:18]([CH2:19][CH2:20][NH2:21])=[N:17][C:16]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[N:15]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1To lithium borohydride (2M solution in THF, 899 μL, 1.8 mmol) was added dropwise trimethylchlorosilane (391 mg, 460 μL, 3.6 mmol) over a period of 5 min at 0-5° C., followed by the dropwise addition of a solution of 2-(1,3-diphenyl-1H-1,2,4-triazol-5-yl)acetonitrile (117 mg, 449 μmol) in THF (1.5 mL). The ice bath was removed after 10 min and the mixture was stirred at 60° C. for 1.5 h. The reaction mixture was cooled to 0-5° C. and 1 mL MeOH was added slowly (bubbling!). After 10 min the ice bath was removed and the mixture was allowed to warm up to RT. The mixture was poured into NaOH (1M aqueous solution, 15 mL) and extracted with dichloromethane (3×50 mL). The combined organic phase was dried over MgSO4, filtered and evaporated to give the product (118 mg with 90% purity, 402 μmol, 89.4%) as yellow viscous oil which was used without further purification.
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