Chlorotrimethylsilane → 2-[N,N-bis(trimethylsilyl)amino]-6-methylpyridine

Participants

Reaction Steps

A 15% n-hexane solution (636 g.) of n-butyllithium was added to a solution of 6-amino-2-methylpyridine (64.8 g.) in tetrahydrofuran (500 ml.) at -20° to -30° C. over one hour, and stirred at -8° to -10° C. for 30 minutes. To the solution was added trimethylsilylchloride (161.7 g.) at -15° to -5° C. over 40 minutes, and the resultant solution was stirred at room temperature overnight. The solution was filtered through by a column packed with silica gel (180 g.), washed with tetrahydrofuran and then the filtrate was concentrated under reduced pressure. The residue was purified by fractional distillation to give 6-[N,N-bis(trimethylsilyl)amino]-2-methylpyridine (117.6 g.), b.p. 95° to 97° C./5-6 mm.

Provenance & Evidence