
TY  - JOUR
A1  - Rasmussen, M 
A1  - Hope, JM 
T1  - Heterocyclic ambident nucleophiles. IV. The alkylation of metal salts of adenine
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1982
VL  - 35
IS  - 3
SP  - 535
EP  - 542
KW  - 
UR  - https://doi.org/10.1071/CH9820535 
N2  - 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. 
ER  -

