Development of methylthiomethyl (MTM) protection for N1 of pyrrolo[2,3-d]pyrimidin-2,4-diones

Article abstract of DOI:10.1016/0040-4039(95)02304-6

This paper describes the application of the methylthiomethyl (MTM) protecting group for the N¹ position in differentially protected pyrrolo[2,3-d]pyrimidin-2,4-diones. By reaction of selected systems with SO₂Cl₂ at low temperature resulted in selective formation of N¹-chloromethyl derivatives. Subsequent heating in aqueous THF with silica gel afforded the deprotected compounds in good yield. Selectivity in the presence of N³ methoxymethyl (MOM) and benzyloxymethyl (BOM), and N⁷ p-nitrophenethyl protection was achieved.