DE2134817A1 - 6 Aminomethylpynmidines and process for their preparation - Google Patents

Description

PATENT LAWYERS

dr. W.Schalk dipl.-ing. P. Wirth dipl.-ing. G. Dannenberg

DR.V. SCHMIED-KOWARZIK · DR. P. WEINHOLD · DR. D. GUDEL

6 FRANKFURT AM MAIN

CR. ESCHENHEIMER STRASSE 39

L.P. 1030

It 0 B "Z A A.G.

Gampel / Wallis

(Management: Basel)

6-aminomethylpyrimidines and process for their preparation

109884/1900

- P mm

The invention relates to 6-aminomethylpyrimidines formula

or acid addition salts of these, where R is hydrogen, alkyl or Cj ^ olo radicals, Ih halogen, ₉ alkoxy or alkyl radicals, R2 is a hydroxyl or amino radical, including substituted amino, B. and R. hydrogen, alkyl or aryl radicals or R- with R. mean a cycloreet. The invention also provides a process for the preparation of 6-aminomethylpyrimidines, which is characterized in that 6-halomethylpyrimidines of the formula

GH

II

in which R and R .. said substituents, and R ^f is a hydroxyl group or halogen and X is halogen, is reacted with ammonia or primary or secondary amines at temperatures of about 0 ° to 120 ⁰ O.

Especially te'öxmen after that. Törfaliren of the invention, 2-alkyl-6-aminoraethyl-4-pyrimidin0le from AEEN corresponding 2-alkyl-6-halomethyl ~ 4 »pyriittiäi22, Qlen by reaction with ammonia

109884 / 19-00

or primary or secondary amines. As alkyl radicals (in formula I "or 'II), there are above all those about 1 to 17, in particular with about 1 to 6, preferably with about 1 to 4 carbon atoms, such as methyl, ethyl, Propyl, isopropyl, butyl radicals, into consideration. As halogen bromine, chlorine, fluorine, preferably chlorine, are used. The cyclic radical is preferably a cycloalkyl radical, in particular with about 5 to 6 carbon atoms.

Shall make 2-alkyl-6-aminomethyl-4-aminopyrimidines are, it is appropriate to start from the 2-alkyl-6-halomethyl-4-pyrimidinols and first replaces the OH group in the 4-position with halogen, for example by reacting with phosphorus halide. In the reaction with ammonia or amines, the halogen in the 4-position is then also replaced by the amine group replaced.

Those made from c -Halogenacetessigderivat with amidines 6-halopyrimidines can also that the latter can be isolated, without further reacted directly with the amines. The reaction solution, which contains the 6-halopyrimidines, is expediently brought to a pH of less than about 7 with mineral acid.

The amines are primary and secondary amines, such as ethylamine, diethylamine, butylamine, aniline, loluidine, phenylethylamine, etc., into consideration. The amines and the ammonia are preferably used in excess.

The implementation in solvents, which depends on Solubility of the reactants both polar solvents, such as water, alcohols, and non-polar liquids, such as toluene, Benzene, can be carried out. The amount of solvents is not critical.

The new compounds according to the invention are effective pesticides, especially insecticides and at the same time are valuable products for the production of these. 10 9884/1900

213A817

example 1

5.0 g of 6-chloromethyl-2-isopropyl-4-pyrimidinol were added to 500 ml concentrated aqueous ammonia and at room temperature ditched. After 48 hours the mixture was evaporated to dryness, taken up in 100 ml of ethanol, the insoluble as a by-product

A-.

The resulting aminomethyl-6- (4-hydroxy-2-isopropyl-6-p; 7rimidyl. ~ (methoxy) -2-isopropylpyrimidine was separated off and the alcohol solution was evaporated to dryness. 4.94 g (91% of theory) were obtained -aminomethyl ^ -isopropyl ^ -pyrimidinol-hydrochlqrid, mp. 218-220 ⁰ C. with decomposition.

Example 2

2.5 g of 6-chloromethyl-2-isopropyl-4-pyrimidinol and 2.5 g of diethylamine were refluxed in 10 ml of water and 10 ml of ethanol. The reaction mixture was evaporated to dryness, treated with 30 ml of acetone, the insoluble diethylaminohydric chloride was separated off, the acetone solution was evaporated to dryness, the residue was dissolved with dilute hydrochloric acid and again evaporated to dryness. There were obtained 3.38 g (97 $ of theory) of 6-Diäthylaminomethyl-2-isopropyl-4-pyTimidinol hydrochloride, mp. 198-200 ⁰ C (dec.).

Example 3

2.5 g of aniline and 2.5 g of 6-chloromethyl-2-isopropyl-4-pyrimidinol were refluxed in 10 ml of water and 10 ml of ethanol. After 1 hour, 50 ml of water were added. Upon cooling, crystalline Allied 2.98 g (92 $ of theory) of 6-anilinomethyl-2-isopropyl-4 ~ pyrimidinol, mp. 156.5 ⁰ C.

Found: C 68.4 H 6.8 N 17.4 0 (calc.) 7.4 - Calculated: 69.11 7.04 17.27 6.58

109884/1900

Claims (5)

Claims or, acid addition salts of these, where R is hydrogen, alkyl or aryl radicals, R _{1 is} halogen, alkoxy or alkyl radicals, R _{2 is} hydroxy or amino radicals, including substituted amino radicals, R, and R. is hydrogen, alkyl or aryl radicals or R- with R. mean a cyclic radical. 2. Process for the preparation of -6-aminomethylpyrimidines according to Claim 1, characterized in that 6-halomethylpyrimidines the formula in which R and R .. are the substituents mentioned, and R ^{f is} hydroxyl or halogen and X is halogen, with ammonia or primary or secondary amines at temperatures of about O ⁰ to 120 ⁰ O converts. 3. The method according to claim 2, characterized in that the ammonia or the Arain is used in excess. 109884/1900 4. The method according to claim 2-3 »characterized in that the reaction is carried out in the presence of a solvent performs. 5. The method according to claim 2-4, characterized in that 6-halo-methyl-pyrimidines of the formula in which R is alkyl radicals ", by reaction with Ammonia or primary or secondary amines to the corresponding 2-alkyl-6-aminomethyl-4-pyrimidinols, 10988W190Q