CAS 769-42-6: Dimethylbarbituric acid

1,3-Dimethylbarbituric acid is used as a catalyst in the Knoevenagel condensation of a series of aromatic aldehydes. It is also used in the synthesis of 5-aryl-6-(alkyl- or aryl-amino)-1,3-dimethylfuro [2,3-d]pyrimidine derivatives and enantioselective synthesis of isochromene pyrimidinedione derivatives. This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

1,3-Dimethylbarbituric acid

Applications 1,3-Dimethyl Barbituric Acid (Urapidil Impurity 4) is a derivative of Barbituric acid (B118650). All of the barbituric acid derivatives which have been reported to have pronounced hypnotic activity are disubstituted in the 5-position. References Gupta, K., et al.: Eur. J. Med. Chem., 17, 448 (1982), Weber, L., et al.: Curr. Med. Chem., 9, 2085 (2002), Skiles, J., et al.: Curr. Med. Chem., 11, 2911 (2004),

1,3-Dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione is a difluoro compound. It has been shown to have hydrogen bonding interactions with copper chloride. FTIR spectroscopy on this molecule shows that the O-H group is involved in hydrogen bonding interaction with the carbonyl group of malonic acid. It also has nucleophilic properties and intramolecular hydrogen bonds. The mechanism for the reaction of 1,3-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione with malonic acid is as follows: The nucleophile attacks the electrophilic carbon atom of the malonic acid and forms an alcoholate intermediate. The reaction proceeds by proton transfer from the hydroxyl group to form an enolate intermediate. Finally, a water molecule is eliminated from the product.

This Thermo Scientific Chemicals brand product was originally part of the Acros Organics product portfolio. Some documentation and label information may refer to the legacy brand. The original Acros Organics product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.