Mild iodine-magnesium exchange of iodoaromatics bearing a pyrimidine ring with isopropylmagnesium chloride.
[reaction: see text] Iodoaromatics bearing a reactive pyrimidine ring underwent a clean iodine-magnesium exchange with isopropylmagnesium chloride in the presence of bis[2-(N,N-dimethylamino)ethyl] ether to provide the corresponding Grignard reagents. The presence of bis[2-(N,N-dimethylamino)ethyl] ether prevented reduction of the pyrimidine ring and addition by isopropylmagnesium chloride. As a result, the newly formed reactive Grignard reagents were allowed to react with electrophiles in a highly selective manner to afford adducts in excellent yields.
Wang
Xiao-jun
XJ
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., Ridgefield, Connecticut 06877, USA. xwang@rdg.boehringer-ingelheim.com
Xu
Yibo
Y
Zhang
Li
L
Krishnamurthy
Dhileepkumar
D
Senanayake
Chris H
CH