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Paper | Regular issue | Vol 24, No. 8, 1986, pp.2179-2194
Published online, 1st January, 1970
DOI: 10.3987/R-1986-08-2179
Regiospecific Alkylation of 9-Benzyl-1,3-dimethyl-6-hydroxypyrimido[2,1-f]purine-2,4,8(1H,3H,9H)-trione

Daniel M. Solomon, David J. Conn, Shing-Chun Wong, and James J. Kaminski*

*Pharmaceutical Research Division, Schering-Plogh Research Institute, Bloomfield, NJ 07003, U.S.A.


The sodium salt of 9-benzyl-1,3-dimethyl-6-hydroxypyrimido[2,1-f]purine-2,4,8(1H,3H,9H)-trione (1a) reacted with a series of alkyl halides in N,N-dimethylformamide to yield 7-carbon alkylated products (1b-1). No O-alkylated products were detected. Isolated yields (not optimized) were in the range of approximately 15-58% for activated halides; non-activated halides were substantially less reactive and gave lower yields. The effects of reaction parameters on reactivity and site of alkylation are discussed, and it is demonstrated that the observed regiospecificity is not the result of an equilibration process.