An expedient method for the synthesis of 6-substituted uracils under microwave irradiation in a solvent-free medium

Tetrahedron Letters

Volumn 46, Issue 34, 2005, Pages 5727-5729

  Devi, Ipsita ^a   Bhuyan, Pulak J ^a  

^a REGIONAL RESEARCH LABORATORY   (India)

Author keywords

6 Amino uracils; 6 Hydroxy uracils; Microwave assisted reactions; Solvent free medium

Indexed keywords

6 AMINOURACIL DERIVATIVE; 6 HYDROXYURACIL DERIVATIVE; ACETIC ACID DERIVATIVE; ACETIC ANHYDRIDE; MALONIC ACID; SODIUM HYDROXIDE; SOLVENT; UNCLASSIFIED DRUG; URACIL DERIVATIVE; UREA DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG PURIFICATION; DRUG SYNTHESIS; MICROWAVE IRRADIATION; POLYMERIZATION; SUBSTITUTION REACTION;

EID: 22544467759     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.06.075     Document Type: Article

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33. Malonic acid 1 (1.24 g, 0.012 mol), N,N-dimethylurea 2a (1.06 g, 0.012 mol) and acetic anhydride 3 (2.448 g, 0.024 mol) were added to the reaction vessel of the microwave reactor (Synthewave 402 monomode reactor from Prolabo) and were allowed to react under microwave irradiation, 40% power at 60 °C, for 7 min. The automatic mode stirrer assisted in mixing and uniform heating of the reactants. The reaction vessel was cooled to room temperature. The small amount of acetic acid produced was removed under reduced pressure and to the residue was added ethanol (10 ml). The resulting light yellow solid was filtered off and recrystallized from ethanol as a white crystalline solid (1.45 g, 78%), mp (121-122 °C).
34. Equimolar amounts of N,N-dimethylurea 2a (1.10 g, 0.0125 mol) and cyanoacetic acid 5 (1.06 g, 0.0125 mol) were thoroughly mixed and then acetic anhydride 3 (1.275 g, 0.025 mol) was added to the reaction vessel of the microwave reactor. The reaction mixture was exposed to microwave irradiation at 40% power for 10 min keeping the temperature below 60 °C. The reaction vessel was cooled to room temperature and ethanol (5 ml) added. A 5% NaOH solution (6 ml) was added with stirring whereby N,N-dimethyl-6-amino-uracil 6a precipitated. The white solid compound was collected by filtration and recrystallized from water as a white crystalline solid (1.54 g, 80%), mp (291-293 °C).