Functionalization of unprotected uracil derivatives using the halogen-magnesium exchange.
[reaction: see text] The reaction of commercially available 5-iodouracil with 2 equiv of MeMgCl in the presence of LiCl, followed by the addition of i-PrMgCl.LiCl, provides the corresponding trimagnesiated species, which reacts with various electrophiles to give selectively 5-functionalized uracil derivatives. This method was also successfully applied to the functionalization of 6-iodouracils including the synthesis of pharmaceutically relevant Emivirine and HEPT precursors.
Kopp
Felix
F
Department Chemie und Biochemie, Ludwig-Maximilians-Universität, Butenandtstrasse 5-13, 81377 Munich, Germany.
Knochel
Paul
P
D006219:Halogens / Q000737:chemistry*; D008274:Magnesium / Q000737:chemistry*; D017616:Magnesium Compounds / Q000737:chemistry; D015394:Molecular Structure; D011687:Purines / Q000737:chemistry; D014498:Uracil / Q000031:analogs & derivatives* / Q000737:chemistry
D006219:Halogens; D017616:Magnesium Compounds; D011687:Purines; D014498:Uracil; D008274:Magnesium