N-methyl-2-pyrrolidone → 2,6-Pyridinediamine, 3-[2-(trimethylsilyl)ethynyl]-

Participants

Reaction Steps

To a mixture of 3-iodo-pyridin-2,6-diamine (20 g) described in Manufacturing Example 4-1, trimethylsilyl acetylene (24 mL), copper(I) iodide (3.3 g), N,N-diisopropylethylamine (19 g), and NMP (290 mL) was added tetrakis(triphenylphosphine)palladium(0) (9.8 g), which was stirred for 30 minutes at room temperature under an argon atmosphere. Water was added to the reaction solution, which was then extracted with ethyl acetate. The ethyl acetate layer thus obtained was washed with water 4 times and dried over sodium sulfate. The sodium sulfate was filtered off, the solvent was evaporated under a reduced pressure, and the residue was purified by NH silica gel chromatography (heptane:ethyl acetate=4:1, then 1:1). The eluate was concentrated under a reduced pressure, and the resulting solids were washed with heptane containing a small amount of ethyl acetate to obtain the titled compound (11 g).

Provenance & Evidence