Ethyl (1,3-diphenyl-1H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-yl)acetate.docVIP

Molbank 2011, M743; doi:10.3390/M743 OPEN ACCESS molbank ISSN 1422-8599 /journal/molbank Short Note Ethyl (1,3-diphenyl-1H-pyrazolo[4,3-e][1,2,4]triazolo[1,5- c]pyrimidin-5-yl)acetate Thoraya A. Farghaly and Sobhi M. Gomha * Department of Chemistry, Faculty of Science, University of Cairo, Giza, 12613, Egypt * Author to whom correspondence should be addressed; E-Mail: s.m.gomha@. Received: 16 August 2011 / Accepted: 13 October 2011 / Published: 10 November 2011 Abstract: Novel ethyl (1,3-diphenyl-1H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5- yl)acetate (5), was prepared via heating of 5-amino-1,3-diphenyl-4,5-dihydro-4-imino-1H- pyrazolo[3,4-d] pyrimidine (1) and diethyl malonate (2) under reflux. The structure of the synthesized compound was assigned on the basis of its elemental analysis, IR, 1H-NMR and mass spectral data. Keywords: pyrazolo[3,4-d]pyrimidine; pyrazolo-triazolo-pyrimidine Pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine exhibits interesting pharmacological activities such as glycogen synthase kinase-3 inhibitors [1], xanthine oxidase (XO) inhibitors [1] and adenosine receptor antagonists [2-11]. These observations led us to synthesize a new pyrazolo[4,3- e][1,2,4]triazolo[1,5-c]pyrimidine from 5-amino-1,3-diphenyl-4,5-dihydro-4-imino-1H-pyrazolo[3,4- d]pyrimidine and diethyl malonate. Results and Discussion 5-Amino-1,3-diphenyl-4,5-dihydro-4-imino-1H-pyrazolo[3,4-d]pyrimidine (1) [12] was allowed to react with diethyl malonate (2) under reflux. The expected product of this reaction was structure 9,11- diphenylpyrazolo[3,4:4,5]pyrimido[1,6-b][1,2,4]triazepin-2,4-dione (3) or 4-ethoxy-9,11- diphenylpyrazolo[3,4:4,5]pyrimido[1,6-b][1,2,4]triazepin-2-one (4) or its isomeric ethyl (1,3- diphenyl-1H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-yl)acetate (5) (Scheme 1). MS, 1H NMR, IR and elemental analyses data of the isolated product were in full agreement with the