2 SYNTHETIC APPROACHES TO 9-DEAZA ANALOGS OF 9-(2,3-DIHYDROXYPROPYL)ADENINE (DHPA)

Two approaches to prepare ypropyl)-2,4-dimethoxy-5H-pyrrolo[3,2-d]pyri midine are described. The first approach starts from 6-cyanomethyl-2,4 -dimethoxy-5-nitropyrimidine which is substituted on its active methyl ene with 2,3-dihydroxypropyl group; the hydrogenation of this compound results in simultaneous reduction of the nitro group and condensed py rrole ring-closure. The second approach to this DHPA analogue consists in addition of alkaline salt of 2,4-dimethoxy-5H-pyrrolo[3,2-d]pyrimi dine on (RS)-2,3-O-isopropylideneglyceraldehyde followed by reductive removal of the hydroxy group.