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1,3-Dimethylbarbituric acid

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1,3-Dimethylbarbituric acid
Names
IUPAC name
1,3-Dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione
Other names
  • 1,3-Dimethylbarbituric acid
  • N,N'-Dimethylbarbituric acid
  • 1,3-Dimethyl-pyrimidine-2,4,6-trione
  • 6-Hydroxy-1,3-dimethyluracil
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.011.101 Edit this at Wikidata
EC Number
  • 212-211-7
UNII
  • InChI=1S/C6H8N2O3/c1-7-4(9)3-5(10)8(2)6(7)11/h3H2,1-2H3
    Key: VVSASNKOFCZVES-UHFFFAOYSA-N
  • O=C1N(C(=O)CC(=O)N1C)C
Properties
C6H8N2O3
Molar mass 156.141 g·mol−1
Acidity (pKa) 4.70
Hazards
GHS labelling:
‹ The template below (GHS corrosion) is being considered for merging with GHS pictogram. See templates for discussion to help reach a consensus. ›
GHS05: Corrosive
‹ The template below (GHS exclamation mark) is being considered for merging with GHS pictogram. See templates for discussion to help reach a consensus. ›
GHS07: Exclamation mark
Danger
H302, H318
P264, P264+P265, P270, P280, P301+P317, P305+P354+P338, P317, P330, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1,3-Dimethylbarbituric acid (N,N'-dimethylbarbituric acid) is an analog of barbituric acid having a methyl group on each of the two nitrogen atoms. It is an intermediate in chemical synthesis, being easily formed by a condensation reaction of 1,3-dimethylurea and malonic acid. A notable application of that reaction and subsequent steps is Emil Fischer's first total synthesis of caffeine.[1] The methylene group (CH2) is fairly acidic, being alpha to two carbonyl groups, and undergoes Knoevenagel condensation reactions with aldehydes[2] and ketones[3] and also acylation reactions.[4] The 1,3-dimethylbarbituric acid substructure motif has found application in several compounds that have cytotoxic properties against cancer cells.[4]

References

[edit]
  1. ↑ Faudone, Giuseppe; Arifi, Silvia; Merk, Daniel (2021). "The Medicinal Chemistry of Caffeine". Journal of Medicinal Chemistry. 64 (11): 7156–7178. doi:10.1021/acs.jmedchem.1c00261. PMID 34019396.
  2. ↑ Asiri, A.M.; Al-Amoudi, M.S. (2006). "Synthesis, characterisation and thermal stability of 5-ferrocenylidene-(1, 3-dimethylbarbituric acid) and 5-ferrocenylidene-(1, 3-diethylthiobarbituric acid)". Pigment & Resin Technology. 35 (5): 270–277. doi:10.1108/03699420610692878.
  3. ↑ Pałasz, Aleksandra; Pałasz, Tadeusz (18 February 2011). "Knoevenagel condensation of cyclic ketones with benzoylacetonitrile and N,N'-dimethylbarbituric acid. Application of sterically hindered condensation products in the synthesis of spiro and dispiropyrans by hetero-Diels–Alder reactions". Tetrahedron. 67 (7): 1422–1431. doi:10.1016/j.tet.2010.12.053.
  4. 1 2 Liu, Yue; Li, Peng-Xiao; Mu, Wen-Wen; Sun, Ya-Lei; Liu, Ren-Min; Yang, Jie; Liu, Guo-Yun (2022). "Design, Synthesis, and Anticancer Activity of Cinnamoylated Barbituric Acid Derivatives". Chemistry & Biodiversity. 19 (2) e202100809. doi:10.1002/cbdv.202100809. PMID 34931450.
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