Synthesis and Reactions of 2-Deoxy-&β-D-ribofuranosyl Derivatives of 3-Aryl-4H-pyrrolopyrimidin-4-imines

Article abstract of DOI:10.1007/BF00824307

3-Aryl-7-(2-deoxy-β-D-erythro-pentofuranosyl)-3,7-dihydro-4H-pyrrolo<2,3-d>pyrimidin-4-imines (4) as well as 4-arylamino-7-(2-deoxy-β-D-erythro-pentofuranosyl)-2-methyl-5-phenyl-7H-pyrrolo<2,3-d>pyrimidines (7) have been synthesized by glycosylation of the sodium salt of the corresponding nucleobases with 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride (2) followed by subsequent deprotection with sodium methoxide in methanol.The deprotected nucleoside 4 undergoes a Dimroth rearrangement on reflux for 24 h in water to furnish the 4-arylamino nucleoside 7. - Keywords: Dimroth rearrangement; Herpes simplex; HIV; Nucleoside synthesis; 4H-Pyrrolo<2,3-d>pyrimidin-4-imine nucleosides