A "Catch and Release" Strategy for the Parallel Synthesis of 2,4,5-Trisubstituted Pyrimidines

Journal of Combinatorial Chemistry

Volumn 6, Issue 1, 2004, Pages 105-111

  Porcheddu, Andrea ^a   Giacomelli, Giampaolo ^a   De Luca, Lidia ^a   Ruda, Antonio Maria ^a  

^a UNIVERSITY OF SASSARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CARBOXYLIC ACID DERIVATIVE; ENAMINE; ESTER; ETHYL 2 (DIMETHYLAMINO) 4 METHYLPYRIMIDINE 5 CARBOXYLATE; GUANIDINE DERIVATIVE; PIPERAZINE; PYRIMIDINE DERIVATIVE; RESIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; COMBINATORIAL CHEMISTRY; CYCLIZATION; HEATING; MICROWAVE IRRADIATION; POLYMERIZATION; RECYCLING; SOLID; SYNTHESIS;

EID: 0942278898     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc034024o     Document Type: Article

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86. For reviews on microwave-assisted combinatorial chemistry, see, for example, the following: (a) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. Increasing Rates of Reaction: Microwave-Assisted Organic Synthesis for Combinatorial Chemistry. J. Comb. Chem. 2002, 4, 95-105. (b) Kappe, C. O. High-Speed Combinatorial Synthesis Utilizing Microwave Irradiation. Curr. Opin. Chem. Biol. 2002, 6, 314-320.
87. See ref 14 and references therein.
88. The MW experiments were performed in a self-tuning single mode CEM Discover Focused Synthesiser apparatus. The instrument continuously adjusted the applied wattage to maintain the desired temperature.
89. To our surprise, in closed vessel system, the process is significantly less effective. Stadler, A.; Pichler, S.; Horeis, G.; Kappe, C. O. Microwave-Assisted Reactions in Open and Closed Vessels. A Case Study. Tetrahedron 2002, 58, 3177-3183.
90. The CEM Discover microwave allows continuous cooling of samples, thus enabling higher levels of irradiation over the time-course of the reaction. The temperature of the reaction mixture was monitored using a temperature and pressure probe inserted through the seal of the reaction tube.
91. Reactions with THF and EtOH solutions were aborted after 5 min above temperatures of 180°C due to pressure maxima.
92. Scott, F. L.; O'Donovan, D. G.; Reilly, J. J. Am. Chem. Soc. 1953, 75, 4053-4054.