Incorporation of 5-substituted uracil derivatives into nucleic acids. Part IV. The synthesis of 5-ethynyluracil
Open Access
- 1 October 1976
- journal article
- research article
- Published by Oxford University Press (OUP) in Nucleic Acids Research
- Vol. 3 (10) , 2845-2850
- https://doi.org/10.1093/nar/3.10.2845
Abstract
5-Acetyluracil (I) has been treated with POCI3 to give 5-(l-chlorovinyl)-2,4-dichloropyrimidine (II). Treatment of II with KOEt gave a mixture of 2-ethoxy-5-ethynyl-4 (3H)-pyrimidinone (IIIA) and 4-ethoxy-5-ethynyl-2 (1 H)-pyrimidinone (IIIB). IIIA and IIIB were isolated and characterised. The mixture of IIIA and IIIB upon treatment with HCI gave 5(1-chlorovinyl)uracil (IV). Reaction of IV with KOEt gave 5-ethynyluracil (V). 5-Ethynyluracil was more easily obtained by the treatment of II with KOH in aqueous dioxan.Keywords
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