Kelley JL, Kelsey JE, Hall WR, Krochmal MP, Schaeffer HJ.
J Med Chem. 1981 Jun;24(6):753-6.A number of pyrimidine acyclic nucleosides were synthesized and tested for activity against herpes simplex virus type 1. Synthesis of 1-[(2-hydroxyethoxy)methyl]cytosine (8) and 1-[(2-hydroxyethoxy)methyl]uracil (14) was accomplished in two or three steps from 2,4-diethoxypyrimidine and 2-(benzoyloxy)ethoxymethyl chloride. The 5-methyl (20), 5-(trifluoromethyl) (21), and 5-fluoro (22) analogues of 14 were available in two steps form the appropriate bis(trimethylsilyl)ated 5-substituted uracil and 2-(acetoxymethoxy)ethyl acetate or 2-(benzoyloxy)ethoxymethyl chloride. Read More