Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Purines. LIX. An Alternative Synthesis of 7-Alkyl-1-methyladenines by Regioselective Alkylation, Fission, and Reclosure of the Adenine Ring
Tozo FUJIITohru SAITOTomoko SUZUKIMayuri KUNUGI
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1994 Volume 42 Issue 1 Pages 151-153

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Abstract
7-Alkyl-1-methyladenines (12a, b) have been synthesized from 1-alkyl-4-aminomidazole-5-carboxamides (5a, b) in two steps [hence from adenine (1) in six steps]. The synthesis started with dehydration (using POCl3-HCONMe2) of 5a, b, readily obtainable from 1 in four steps according to previously reported procedures, and proceeded through cyclization between the resulting 4-(dimethylaminomethyleneamino)imidazole-5-carbonitrile derivatives (8a, b) and MeNH2. Similar cyclization between 1-benzyl-4-(ethoxymethyleneamino)imidazole-5-carbonitrile (11c) and MeNH2 yielded 7-benzyl-1-methyladenine (12c).
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