Mannich Reactions of Pyrimidines. II. 2-Methylmercapto-4-methyl-6-hydroxypyrimidine and 2-Thio-6-methyluracil^1,2

Thio Analogs of Pyrimidine Bases: Synthesis, Spectroscopic Study, and In Silico Biological Activity Evaluation of New 2-o-(m- and p-)Chlorobenzylthio-6-Methyl-5-Piperidino-(Morpholino-)Methyluracils

“…2-thio-5-piperidinomethyl-6-methyluracil [9], 2-thio-5-morpholinomethyl-6-methyl-uracil [8], and 2- o -( m - and p -)-chlorobenzylthio-6-methyluracils [17] have been obtained according to the literature.…”

“…General procedure A: 0.2 g (0.8 mmole) of 2-thio-5-piperidino-(morpholino-)-methyl-6-methyluracils [8, 9] was dissolved with stirring in room temperature in 2.5 mL of 3 N NaOH in methanol. Next, to the solution 0.116 mL (0.9 mmole) of o -chlorobenzyl chloride or 0.146 g (0.9 mmole) of p -chlorobenzyl chloride was added.…”

“…Chemical modification of these compounds have led to a large number of mono- and di- S and N -substituted analogs showing therapeutic properties, especially antivirial, antithyroid, and antitumor activities [1–7]. The antimetabolites of 5,6-dimethyluracil 5-morpholinomethyl-6-methyl-2-thiouracil [8] and 5-piperidinomethyl-6-methyl-2-thiouracil [9] have been synthesized via the Mannich reaction. However, to the best of our knowledge no work has been published on the synthesis as well as on physicochemical properties of the monochlorobenzylthio-substituted derivatives of these compounds.…”

Recent advances in thymidine phosphorylase inhibitors: syntheses and prospective medicinal applications

“…The synthesis of 6-methyl-3H-pyrimidin-4-one 84 was accomplished by desulphurization reaction of 6-methyl-2-thiouracil 83 by hydrogenolysis in the presence of alkaline solution of Raney nickel. 48 The chlorination of compound 84 at C-5 position with N -chlorosuccinimide (NCS) in acetic acid afforded compound 85 in 73.7% yield. 49 5-Chloro-6-(chloromethyl)-3H-pyrimidin-4-one 86 was synthesized in 10.2% yield by radical halogenation using benzoyl peroxide and NCS.…”