PYRIMIDINE NUCLEOSIDES .3. NUCLEOSIDE DERIVATIVES OF CERTAIN 4-SUBSTITUTED 6-PYRIMIDONES

The synthesis of 4,6-disubstituted pyrimidine nucleosides possessing two hydrogen-bonding groups has been achieved for the first time using a modified Hilbert-Johnson procedure. 4-Amino-1-(β-D-ribofuranosyl)-6-pyrimidone (8) and 4-amino-1-(2-deoxy-β-D-ribofuranosyl)-6-pyrimidone (9) have been prepared by direct utilization of 4-amino-6-pyrimidone (5) via silylation and subsequent treatment with the appropriate glycosyl halide in acetonitrile. This procedure applied to 4-methylthio-6-pyrimidone gave 4-methylthio-1-(β-D-ribof ur anosyl)-6-pyrimidone (2). Reductive desulfurization of 2 gave 1-(β-D-ribofuranosyl)-6-pyrimidone (3). Oxidation of a blocked derivative of 2 provided the corresponding methyl sulfone 7 which was successfully converted into 8 and also into 4-methoxy-1-(β-D-ribofuranosyl)-6-pyrimidone (6). © 1969, American Chemical Society. All rights reserved.