DEVELOPMENT OF METHYLTHIOMETHYL (MTM) PROTECTION FOR N-1 OF PYRROLO[2,3-D]PYRIMIDIN-2,4-DIONES

Authors
EDSTROM ED FENG XQ TUMKEVICIUS S
Citation
Ed. Edstrom et al., DEVELOPMENT OF METHYLTHIOMETHYL (MTM) PROTECTION FOR N-1 OF PYRROLO[2,3-D]PYRIMIDIN-2,4-DIONES, Tetrahedron letters, 37(6), 1996, pp. 759-762
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
6
Year of publication
1996
Pages
759 - 762
Database
ISI
SICI code
0040-4039(1996)37:6<759:DOM(PF>2.0.ZU;2-8
Abstract
This paper describes the application of the methylthiomethyl (MTM) pro tecting group for the N-1 position in differentially protected pyrrolo [2,3-d]pyrimidin-2,4-diones. By reaction of selected systems with SO2C l2 at low temperature resulted in selective formation of N-1-chloromet hyl derivatives. Subsequent heating in aqueous THF with silica gel aff orded the deprotected compounds in good yield. Selectivity in the pres ence of N-3 methoxymethyl (MOM) and benzyloxymethyl (BOM), and N-7 p-n itrophenethyl protection was achieved.