DE156055C - - Google Patents

Description

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IMPERIAL

PATENT OFFICE.

It has been found that by the action of the methylene group by Metals such as potassium, sodium, substituted derivatives of cyanoacetic ester on thiourea and its monoalkyl derivatives of the formula

/ NH. R. C ^ -SH

sulfur-containing pyrimidine derivatives of the formula N (RJ-CO
■ II
C SH CH ₂
Il I

.. N C: NH

receives.

The new thiopyrimidine derivatives differ from those according to the method of patents 134984 and 135371 available, in the 2-position alkyl radicals respectively. the imido group-containing pyrimidine derivatives very much essentially in that they are smoothly BEZW in hypoxanthine. its on nitrogen let transfer alkylated derivatives. The representation of these last-mentioned bodies takes place best after that of W. Traube (reports of the former Ges. 33, 1900, page 3035 and 3036) for the production of guanine from 2 ^ -Diamino-o-oxypyrimidm.

method. This is done by converting the sulfur-containing pyrimidine derivatives of the above formula into the nitroso compounds, Reduction of the bodies obtained in this way to ■ the 4 · 5 - diaminothiooxypyrimidines and causing ring closure by boiling these products with formic acid. From the thiohypoxanthine obtained in this way or its alkylation products can then easily by oxidation hypoxanthine or the corresponding derivatives of this Body are preserved.

Example 1.

To a solution of 19.5 parts of potassium in 500 parts of absolute alcohol is added 57 parts Gyänessigsäureäthylester, then sets to the. Potassium cyanoacetate obtained in this way 57 parts of thiourea are added and the mixture is heated to the boil in a water bath for one to two hours. The excreted potassium salt becomes filtered off, dissolved in water and weakly acidified with acetic acid. The new condensation product separates out and can be cleaned by recrystallization from hot water. It forms colorless Crystals that are easily soluble in hot water as well as in acids and alkalis, Slightly soluble, on the other hand, in cold water and in alcohol. It decomposes when heated Product without melting. With nitrous acid it forms a sparingly soluble isonitroso compound, whose ammonia salt crystallizes in brown needles.

Example 2.

0.75 parts of sodium are dissolved in absolute alcohol and mixed with 5 parts of allyl thiourea and 4.5 parts of ethyl cyanoacetate crosslinked. After two hours Cooking is the major part of the condensation product deposited as the sodium salt and

is then, as indicated in Example ι, isolated. The product obtained in this way is very difficult to dissolve in water and alcohol in the cold and more readily soluble in the heat. It can go out these solvents are recrystallized. It is insoluble in ammonia and is made from Alkali solutions have already been absorbed in the cold and precipitated from these solutions with acetic acid.

Example 3.

4 parts of methylthiourea are added to a solution of 0.75 parts of sodium in absolute alcohol and 4.5 parts of ethyl cyanoacetate were added and the mixture was boiled for a few hours. After this time it is evaporated and the thiopyrimidine derivative precipitated using acetic acid. The product thus obtained forms colorless needles that are sparingly soluble in alcohol even at the boiling point. Easier it dissolves in hot water, from which it crystallizes in fine needles when it cools. Alkalis easily dissolve the body even in the cold, ammonia only with difficulty. From the alkaline solutions it becomes up The addition of acids is again precipitated.

Claims (1)

Patent claim: Process for the preparation of thiopyrimidine derivatives, consisting in the fact that the derivatives of cyanoacetic esters which are substituted by metals in the methylene group can act on thiourea or its monoalkyl derivatives.