769-42-6 Usage
Description
1,3-Dimethylbarbituric acid, also known as 1,3-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione, is an organic compound that belongs to the barbituric acid family. It is a white crystalline solid with the molecular formula C6H8N2O3. 1,3-Dimethylbarbituric acid is characterized by the presence of two methyl groups attached to the 1,3-positions of the barbituric acid structure, which imparts unique chemical properties and reactivity to the molecule.
Uses
1,3-Dimethylbarbituric acid is used as a catalyst in the Knoevenagel condensation of a series of aromatic aldehydes. This reaction is an important organic synthesis process that involves the condensation of an aldehyde with an active methylene compound to form a new carbon-carbon bond. The use of 1,3-Dimethylbarbituric acid as a catalyst enhances the reaction rate and selectivity, making it a valuable component in the synthesis of various organic compounds.
Used in Pharmaceutical Industry:
1,3-Dimethylbarbituric acid is used as a key intermediate in the synthesis of 5-aryl-6-(alkylor aryl-amino)-1,3-dimethylfuro[2,3-d]pyrimidine derivatives. These derivatives are of significant interest in the pharmaceutical industry due to their potential therapeutic applications, such as their use as antiviral, anticancer, and anti-inflammatory agents. The unique structural features of 1,3-Dimethylbarbituric acid enable the formation of these biologically active compounds, contributing to the development of new drugs.
Used in Enantioselective Synthesis:
1,3-Dimethylbarbituric acid is also used in the enantioselective synthesis of isochromene pyrimidinedione derivatives. Enantioselective synthesis is a crucial aspect of modern organic chemistry, as it allows for the preparation of chiral compounds with a specific enantiomeric excess. This is particularly important in the pharmaceutical industry, where the desired biological activity is often associated with a specific enantiomer. The use of 1,3-Dimethylbarbituric acid in this process aids in the development of enantiomerically pure compounds with potential applications in various therapeutic areas.
Purification Methods
Crystallise the acid from water and sublime it in a vacuum. Also purify it by dissolving 10g in 100mL of boiling CCl4/CHCl3 (8:2) (1g charcoal), filtering and cooling to 25o. Dry it in vacuo [Kohn et al. Anal Chem 58 3184 1986]. [Beilstein 24 III/IV 1875.]
Check Digit Verification of cas no
The CAS Registry Mumber 769-42-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 7,6 and 9 respectively; the second part has 2 digits, 4 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 769-42:
(5*7)+(4*6)+(3*9)+(2*4)+(1*2)=96
96 % 10 = 6
So 769-42-6 is a valid CAS Registry Number.
InChI:InChI=1/C6H8N2O3/c1-7-4(9)3-5(10)8(2)6(7)11/h3H2,1-2H3
769-42-6Relevant articles and documents
Kinetics of Electrophilic Alkylations of Barbiturate and Thiobarbiturate Anions
Schade, Alexander,Tchernook, Ivan,Bauer, Mirko,Oehlke, Alexander,Breugst, Martin,Friedrich, Joachim,Spange, Stefan
, p. 8476 - 8488 (2017)
Second-order rate constants (k2) of the reactions of various barbiturate anions such as the parent barbiturate, 1,3-dimethylbarbiturate, 2-thiobarbiturate, and 1,3-diethyl-2-thiobarbiturate with diarylcarbenium ions and Michael acceptors have b
Ultrasound-assisted rapid synthesis of 2-aminopyrimidine and barbituric acid derivatives
Bayramo?lu, Duygu,Kurtay, Gülbin,Güllü, Mustafa
, p. 649 - 658 (2020/02/11)
Novel, inexpensive, and relatively expeditious procedure to achieve the synthesis of different 2-aminopyrimidine and barbituric acid derivatives is presented here, starting from readily available compounds such as guanidine hydrochloride, urea, 1,3-dialkylurea, or thiourea. Under ultrasonic irradiation, base-driven (Na2CO3, NaOH, or NaOC2H5) heterocyclization reactions of the aforementioned substrates with diethyl malonate, diethyl-2-alkyl malonate, pentane-2,4-dione, or ethyl-3-oxobutanoate yielded corresponding products. Significant advantages of this sonochemical synthetic protocol with regard to the conventional thermal methods include easy reaction setup and work-up steps, reasonably mild conditions, shorter reaction times (~30 min) and comparably high product yields. The characterization of the synthesized compounds was based on melting points, FT-IR, GC-MS, 1H-NMR techniques, and the obtained data were also checked from the previously published studies.
Selective and facile oxidative desulfurization of thioureas and thiobarbituric acids with singlet molecular oxygen generated from trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane
Azarifar, Davood,Golbaghi, Maryam
, p. 1 - 13 (2016/02/12)
An efficient and facile procedure using trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane has been developed for oxidative desulfurization of thioureas and thiobarbituric acids. The reactions proceeded smoothly very fast under mild conditions in basic media at room temperature to afford the respective ureas in excellent yields. Simple procedure and work up, mild conditions, high yields, short reaction times, use of highly potent and non-toxic oxidant are the main merits of the present method.