Poster presentation
51
CATALYTIC OXIDATION OF 6-METHYLURACIL
Y.Z. Khazimullina, A.R. Gimadieva, A.G. Mustafin
Ufa Institute of Chemistry UFIC RAS, 71, Prospekt Oktyabrya, Ufa, 450054 Russia
It is well known that pyrimidine bases are an integral part of DNA and RNA in
organisms; therefore, derivatives of this class of compounds
are used as the active
ingredient of many drugs. For example, there are a number of drugs based on uracil due
to its wide spectrum of pharmacological activity: fluorouracil (antitumor activity),
zidovudine (antiviral activity), 6-methyluracil (immunomodulatory action), etc. [1]. One
of the compounds with proven anti-inflammatory, immunotropic activity is 5-hydroxy-
6-methyluracil registered as a drug Immureg [2]. One of the methods of obtaining
oxymethyluracil is the Elbs oxidation of 6-methyluracil:
However, according to the classical reaction of persulfate oxidation, the yield of the
target product does not exceed 15%, therefore, a modification of the Elbs reaction was
carried out - catalysts (phthalocyanines of various metals) were used, which
significantly
changed the picture, increasing the yield of the intermediate product
(further PP) 5-ammoniumsulfate-6-methyluracil to 85-88% [3], the second stage of acid
hydrolysis proceeds quantitatively, forming 5-hydroxy-6-methyluracil (further OMU).
Dependence of PP yield on the type and amount of catalyst (0.01% weight)
(molar ratio 6-methyluracil:NaOH:ammonium persulfate = 1:4.1:1.5)
№
Catalyst
PP yield, %
OMU yield, %
1
Fc Co
87
83
2
Fc Fe(II)
89
85
3
Fc Fe(Ш)
82
79
4
Fc Ni
71
67
5
Fc Mn
72
67
6
Fc Zn
69
61
References:
1.Gimadieva A.R., Chernyshenko Y.N., Abdrakhmanov I.B., Mustafin A. G.
Synthesis, modifications and biological activity of uracils. Ufa: Gilem, 2013. 176 с.
2. Permission of the Pharmacological State Committee
for medical use from
11.11.1993, reg. no. 96/302/2; 96/302/12.
3.Gimadieva A.R., Khazimullina U.Z., Abdrakhmanov I.B., Mustafin A.G. Method
for obtaining 5-hydroxy-6-methyluracil and 5-hydroxy-1,3,6-trimethyluracil - effective
immunomodulators and antioxidants / Journal of Applied Chemistry, 2022. Т.95. Vol.3.
382-388 с.