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KMID : 1059519990430060670
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Journal of the Korean Chemical Society
1999 Volume.43 No. 6 p.670 ~ p.675
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The Synthesis of 6-[1-(4-Ribitylanilino)ethyl]-1,3-dimethyllumazine Related to Methanopterin
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Jang Yong-Jin
Kim Yeon-Hee
Kang Yong-Han
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Abstract
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6-[1-(4-Ribitylanilino)ethyl]-1,3,7-trimethyllumazine (2), which is related to pteridine moiety of methanopterin, was synthesized. 4-Ribitylaniline derivative was prepared from D-ribose and N-benzoyl-4-bromoaniline (7) as the starting materials through several steps. 6-Acetyl-1,3,7-trimethyllumazine (4) was obtained from the reaction of 4-amino-1,3-dimethyI-5-nitrosouracil (3) with 2,4-pentanedione by Timmis reaction. Compound 4 was convened to 6-(1-chloroethyl)-1,3,7-trimethyllumazin (6) by the reduction with sodium borohydride and followed by chlorination with thionyl chlride. The nucleophilic displacement reaction of compound 6 with 4-(2,3:4,5-di-O-isoㅡpropylidene-D-ribityl)aniline (13) in anhydrous DMF yielded 6-[1-{4-(2,3:4,5-di-O-isopropylidene-D-ribityl)anilino}ethyl]-1,3,7-trimethyllumazine (14). The target molecule 2 was obtained by the hydrolysis of compound 14 in the presence of an acid catalyst.
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