Synthesis of deuterium labeled 2,4-dipyrrolidinylpyrimidine as a chemical probe for P450 mediated oxidation of tirilazad mesylate

Article abstract of DOI:10.1002/(SICI)1099-1344(199807)41:7<577::AID-JLCR108>3.0.CO;2-N

Selective deuterium labelled pyrrolidinylpyrimidine analogs were synthesized to provide a probe for the metabolite identification of Tirilazad. Synthesis of 2-[D₈]-pyrrolidinyl-4-pyrrolidinylpyrimidine (1) and 4-[D₈]pyrrolidinyl-2-pyrrolidinylpyrimidine (2) was accomplished by reaction of pyrrolidine (3) with 2,4-dichloropyrimidine (4), separation of the two reaction products (5 and 6) and reaction of these products with [D₈]pyrrolidine (7). [D₁₆]2,4-dipyrrolidinylpyrimidine (8) was prepared by reaction of [D₈]pyrrolidine (7) with 2,4-dichloropyrimidine (4).