C–C (alkynylation) vs C–O (ether) bond formation under Pd/C–Cu catalysis: synthesis and pharmacological evaluation of 4-alkynylthieno[2,3-<i>d</i>]pyrimidines
Dhilli Rao GorjaInstitute of Life Sciences, University of Hyderabad Campus, Gachibowli, Hyderabad-500 046, IndiaK. Shiva KumarInstitute of Life Sciences, University of Hyderabad Campus, Gachibowli, Hyderabad-500 046, India andK. MukkantiChemistry Division,Manojit PalInstitute of Life Sciences, University of Hyderabad Campus, Gachibowli, Hyderabad-500 046, India and
2011en
ABI
Abstract
The Pd/C-CuI-PPh(3) catalytic system facilitated C-C bond formation between 4-chlorothieno[2,3-d]pyrimidines and terminal alkynes in methanol with high selectivity without generating any significant side products arising from C-O bond formation between the chloro compounds and methanol. A variety of novel 4-alkynylthieno[2,3- d]pyrimidines were prepared via alkynylation of 4-chlorothieno[2,3-d]pyrimidines in good to excellent yields. Some of the compounds synthesized were tested for cytotoxic activity in vitro.
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