Purines. XXII. Methylation of 1-, 3-, 7-, 9-, and N^6-Methyladenines Bearing a Methoxyl Group at the N^6-Position : A Synthesis of 7,9-Dimethyladenine
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概要
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In order to investigate the effect of the N^6-methoxy group on the site of methylation, N^6-methyl-(27), 1-methyl-(17), 3-methyl-(11), 7-methyl-(7), and 9-methyl-N^6-methoxyadenine (2) were methylated with an excess of MeI in AcNMe_2. The products isolated were the 3-methylated product 12・HClO_4 (67%yield) and 9-methylated product 3 (18%) from 27 ; 3-methylated product 15 (X=I) (44%) and 9-methylated product 18・HClO_4 (38%) from 17 ; 15 (X=I) (40%) and 12・HClO_4 (36%) from 11 ; 9-methylated product 5 (X=I) (36%) and 3-methylated product 8 (44%) from 7 ; 5 (X=I) (59%) and 3・HI (24%) from 2. Further methylation of 18 in a similar manner was found to give N^6-methoxy-1,7,9-trimethyladeninium iodide (33 : X=I) in 92% yield. A similar methylation of the betaine 32,generated from 5 (X=I) by treatment with 1,8-diazabicyclo [5. 4. 0] undec-7-ene (DBU), also produced 33 (X=I) in fair yield. The 7,9-dimethyl derivative 5 (X=I) thus obtained was converted into the perchlorate 5 (X=ClO_4), and hydrogenolysis of 5 (X=ClO_4) using Pd-C and hydrogen furnished hitherto unknown 7,9-dimethyladeninium perchlorate (6 : X=ClO_4) in good yield. The substrates 11 and 27 used for the methylation study were prepared in 87 and 86% yields from 3-methyl-6-methylthiopurine (10) and 6-chloropurine (26) by amination with methoxyamine and N, O-dimethylhydroxylamine, respectively. For the synthesis of the substrate 17,1-methoxyadenosine (25) was methylated to give the N^6-methyl derivative 23. Treatment of 23 with hot water and hydrolysis of the resulting isomer 21 with 98% formic acid afforded the desired compound 17.
- 公益社団法人日本薬学会の論文
- 1983-09-25
著者
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斎藤 徹
Faculty Of Pharmaceutical Sciences Kanazawa University
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板谷 泰助
Faculty of Pharmaceutical Sciences, Kanazawa University
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田中 孚美子
Faculty Of Pharmaceutical Sciences Kanazawa University
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板谷 泰助
金沢大学薬学部
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Saito T
Research And Development Headquarters Hokurikit Seiyaku Co. Ltd.
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山本 清美
Faculty of Pharmaceutical Sciences, Kanazawa University
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山本 清美
Faculty Of Pharmaceutical Sciences Kanazawa University
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毛利 和代
Faculty of Pharmaceutical Sciences, Kanazawa University
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毛利 和代
Faculty Of Pharmaceutical Sciences Kanazawa University
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