Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 13, Pages 5309-5319Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo2006494
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Funding
- Academy of Sciences of the Czech Republic [Z4 055 0506]
- Ministry of Education [LC06077]
- Gilead Sciences, Inc. (Foster City, CA, U.S.)
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A new regioselective synthesis of 5- and 6-aryluracil bases based on direct C-H arylations of diverse 1,3-protected uracils has been developed. Benzyl-protected uracils were selected as the most practical in terms of stability during the arylation and facile cleavage of the benzyl groups. Pd-catalyzed C-H arylations in the absence of CuI gave preferentially 5-aryl-, whereas the reactions in the presence of CuI gave 6-aryl-1,3-dibenzyluracils. Final deprotection either by transfer hydrogenolysis over Pd/C or by treatment with BBr(3) gave the desired free arylated uracil bases in good yields.
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