Phosphorus oxychloride → HCID 86742690, compound

Participants

Reaction Steps

The method of this invention comprises the steps of a) reacting 6-cyanopurine with bis(trimethylsilyl)trifluoroacetamide in acetonitrile under reflux and thereafter with tetra-O-acetyl-β-D-ribofuranose in the presence of trimethylsilyltrifluoromethanesulfonate to stereospecifically produce 9-(tri-O-acetyl-β-D-ribofuranosyl)-6-cyanopurine in high yield; b) reacting said 9-(tri-O-acetyl-β-D-ribofuranosyl)-6-cyanopurine with methanolic ammonia in a sealed pressure vessel at ambient temperature to produce N4 -(β-D-ribofuranosyl)pyrimido[4,5-d]pyrimidine-4,8-diamine; c) reacting said N4 -(β-D-ribofuranosyl)pyrimido[4,5-d]pyrimidine-4,8-diamine with phosphoryl chloride in trimethylphosphate at a temperature below about 10° C. to produce N4 -5-O-phosphono-β-D-ribofuranosyl)pyrimido[4,5-d]pyrimidine-4,8-diamine or, alternatively reacting said N4 -(β-D-ribofuranosyl)pyrimido[4,5-d]pyrimidine-4,8-diamine with acetic anhydride in the presence of an acid scavenger to produce N4 -(2,3,5-tri-O-acetyl-β-D-ribofuranoxyl)pyrimido[4,5-d]pyrimidine-4,8-diamine.

Provenance & Evidence