A Two Step Synthesis of the Nucleoside Q Precursor 2-Amino-5-cyanopyrrolo[2,3-d]pyrimidin 4-one (PreQo)
- 1 September 1996
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 26 (17) , 3317-3322
- https://doi.org/10.1080/00397919608004641
Abstract
PreQo (1) is prepared in a 70 % yield by the condensation of chloro(formyl)acetonitrile (2) with 2,6-diaminopyrimidin-4-one (3), and subsequently converted to its amide derivative 5. Isolation of the intermediate 4 in the condensation reaction was also observed giving further insight into the proposed mechanism.Keywords
This publication has 12 references indexed in Scilit:
- A short and efficient synthesis of echiguanines A and B: Potent inhibitors of phosphatidylinositol-4-kinaseTetrahedron Letters, 1994
- Total and stereospecific synthesis of cadeguomycin, 2′deoxycadeguomycin, ara-cadeguomycin, and certain related nucleosidesJournal of the Chemical Society, Perkin Transactions 1, 1989
- Kanagawamicin, a New Aminonucleoside Analog Antibiotic from Actinoplanes kanagawaensisHETEROCYCLES, 1983
- SYNTHESIS OF 7-CYANO-7-DEAZAGUANINE, ONE OF THE NUCLEOSIDE Q (QUEUOSINE) PRECURSORS FOR THE POST-TRANSCRIPTIONAL MODIFICATION OF tRNAChemistry Letters, 1980
- Transfer ribonucleic acid guanine transglycosylase isolated from rat liverBiochemistry, 1980
- Studies directed toward a total synthesis of nucleoside Q. Annulation of 2,6-diaminopyrimidin-4-one with .alpha.-halo carbonyls to form pyrrolo[2,3-d]pyrimidines and furo[2,3-d]pyrimidinesThe Journal of Organic Chemistry, 1978
- Total synthesis of nucleoside QTetrahedron Letters, 1977
- The synthesis of 2‐amino‐7‐(β‐D‐ribofuranosyl)pyrrolo[2,3‐d]‐pyrimidin‐4‐one (7‐deazaguanosine), a nucleoside Q and Q* analogJournal of Heterocyclic Chemistry, 1976
- Synthesis of 2-amino-5-cyano-7-(.beta.-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidin-4-one. An important precursor for the synthesis of nucleoside Q and Q*Journal of the American Chemical Society, 1976
- Aromaticity in heterocyclic systems. II. the application of N.M.R. in a study of the synthesis and structure of certain lmidazo[1,2‐c]pyrimidines and related pyrrolo[2,3‐d]pyrimidinesJournal of Heterocyclic Chemistry, 1964