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Journal ArticleDOI

Heterocyclic ambident nucleophiles. IV. The alkylation of metal salts of adenine

M Rasmussen, +1 more
- 01 Jan 1982 - 
- Vol. 35, Iss: 3, pp 535-542
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TLDR
The N3 : N7 : N9 alkylation patterns for reactions of the lithium, sodium, and potassium salts of adenine with various alkylating agents in dimethyl sulfoxide were determined by 1H n.m. spectroscopy as discussed by the authors.
Abstract
The N3 : N7 : N9 alkylation patterns for reactions of the lithium, sodium, and potassium salts of adenine with various alkylating agents in dimethyl sulfoxide were determined by 1H n.m.r. spectroscopy. Only for the Li+ salt was any significant effect of ionic association noticed. Of the alkylating agents used, only chloromethyl pivalate gave a concentration dependent alkylation pattern. The latter effect was most pronounced with the heterogeneous alkylation conditions of anhydrous Na2CO3/HCONMe2, adenine, and chloromethyl pivalate; here, increasing concentrations changed the main reaction from N7- to N9-alkylation. Solvent effects on the alkylation patterns were also studied. Within the common dipolar aprotic solvent group, (Me2N)3PO, HCONMe2 and Me2SO, effects were small; in protic solvents, particularly formamide, enhanced N3-alkylation was observed.

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