Sulfur-containing pyrimidines as key intermediates in parallel synthesis of 2,6,8,9-tetra-substistuted purines

ORGN 557

Xu Bai, Jinglin Liu, Qun Dang, Zhonglin Wei, Jinchang Wu, and Hengbin Zhang. Center for Combinatorial Chemistry and Drug Discovery, Jilin University, 75 Jinlai St., Changchun, Jilin 130012, China

A synthetic route for 2,6,8,9-tetra-substituted purines shown in the following Scheme was developed. The synthesis comprises of the following sequential manipulations: mono-substitution of 2-substituted 4,6-dichloro-5-nitropyrimidines by benzyl mercaptan, followed by amine substitution of the remaining chloro group, reduction of the nitro group, cyclization to form the purine ring, oxidation of sulfide to sulfone, and subsequent amine substitution to yield fully substituted purines. This procedure not only provided a library of tetra-substituted purine analogs but also the model study of sulfur linked solid phase (Merrifield resin) synthesis of purine libraries.

Combinatorial, parallel, and solid-phase chemistry 1:00 PM-5:00 PM, Wednesday, March 31, 2004 Anaheim Convention Center -- 303A, Oral Division of Organic Chemistry The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004