CS265783B1 - Preparation of 1-methyl-5-methylamino-6-aminouracil - Google Patents

Preparation of 1-methyl-5-methylamino-6-aminouracil Download PDF

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CS265783B1
CS265783B1 CS878786A CS878687A CS265783B1 CS 265783 B1 CS265783 B1 CS 265783B1 CS 878786 A CS878786 A CS 878786A CS 878687 A CS878687 A CS 878687A CS 265783 B1 CS265783 B1 CS 265783B1
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Czechoslovakia
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methylamine
methyl
aminouracil
formula
methylamino
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CS878786A
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Czech (cs)
Slovak (sk)
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CS878687A1 (en
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Ladislav Ing Csc Stibranyi
Miroslav Ing Csc Veverka
Jan Ing Csc Jendrichovsky
Jozef Ing Nevydal
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Stibranyi Ladislav
Veverka Miroslav
Jendrichovsky Jan
Nevydal Jozef
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Application filed by Stibranyi Ladislav, Veverka Miroslav, Jendrichovsky Jan, Nevydal Jozef filed Critical Stibranyi Ladislav
Priority to CS878786A priority Critical patent/CS265783B1/en
Publication of CS878687A1 publication Critical patent/CS878687A1/en
Publication of CS265783B1 publication Critical patent/CS265783B1/en

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Predmetom riešenia je spósob přípravy l-metyl-5-metylamíno-6-amínouracilu reakciou kvapalného bezvodého metylamínu s 1-metyl- -5-bróm-6-amínouracilom pri teplotách -6 °C až 80 °C a molárnych pomeroch metylamínu: :uracil = 4:1 až 50:1. Předmětná zlúčenina slúži ako medziprodukt pri príprave teo- bromínu.The present invention provides a process for the preparation of 1-methyl-5-methylamino-6-aminouracil by reaction of liquid anhydrous methylamine with 1-methyl-5-bromo-6-aminouracil at temperatures of -6 ° C to 80 ° C and methylamine molar ratios of: uracil = 4: 1 to 50: 1. The compound in question serves as an intermediate in the preparation of the bromo bromine.

Description

265783 2265783 2

Vynález se týká spůsobu přípravy l-metyl-5-metylamíno-6-amínouracilu vzorca X 0 /1/, I ΛΜΗ- CH, 'NH, CH, ktorý je medziproduktom pre výrobu teobrominu.The present invention relates to a process for the preparation of 1-methyl-5-methylamino-6-aminouracil of formula X 0/1, I-CH, NH, CH, which is an intermediate for theobromine production.

Bolí popísané přípravy predraetnej zlúčeniny vzorca I z 1-metyl-5-bróm-6-amínouraciluvzorca IIPreparations of a precursor compound of formula I from 1-methyl-5-bromo-6-aminouracil sample II have been described.

Br Ό I '‘NH2CH3 /11/ působením metylamínu v pyridine (Jap. pat. 7 411 389) alebo vo vodnom roztoku metylamínu(Polský pat. 42 976).Br Ό I ‘NH 2 CH 3/11) by treatment with methylamine in pyridine (Jap. Pat. 7 411 389) or in aqueous methylamine (Polish Pat. No. 42,976).

Spůsobom podlá vynálezu sa předmětná zlúčenina vzorca I získává z brómderivátu vzorca IIpůsobením nadbytku kvapalného bezvodého metylamínu, ktorý působí jednak ako reakčné činidlo,jednak ako rozpúštadlo. Reakcia prebieha pri teplotách od -6 °C do 80 °C v uzavretých nádobáchza tlaku, je potřebné použit nadbytok metylamínu voči brómderivátu vzorca II v pomere 4:1 až50:1. Výhodou takéhoto provedenia reakcie je vysoká selektivita reakcie spůsobená bezvodýmpřevedením procesu, ako aj nadbytkom metylamínu, ktorý sa dá lahko recyklovat po ukončenireakcie oddestilovaním. Metylamín z reakčnej zmesi vydestiluje a skvapalní sa solankovýmchladičom, čo umožňuje priemyselné využitie reakcie. V člalšom je predmet vynálezu objasněný na príkladoch bez toho, aby sa na tieto výlučnéobmedzoval. Přikladl 4,4 g l-metyl-6-amíno-5-brómuracilu (0,02 M) sa zmieša k 25 ml bezvodého metylamínua zmes sa v uzavretej tlakovej trubici zahrieva na teplotu 40 °C 4 hodiny.According to the present invention, the subject compound of formula (I) is obtained from a bromo derivative of formula (II) by causing an excess of liquid anhydrous methylamine which acts both as a reagent and as a solvent. The reaction proceeds at temperatures from -6 ° C to 80 ° C in closed pressure vessels, an excess of methylamine to the bromo derivative of formula II is needed in a ratio of 4: 1 to 50: 1. The advantage of such a reaction is the high selectivity of the reaction caused by the anhydrous conversion of the process, as well as the excess of methylamine, which can be easily recycled after completion of the distillation reaction. Methylamine from the reaction mixture is distilled and liquefied with brine to allow the industrial reaction to proceed. In the following, the subject matter of the invention is illustrated by the following examples, without being limited thereto. EXAMPLE 1 4.4 g of 1-methyl-6-amino-5-bromouracil (0.02 M) are mixed with 25 ml of anhydrous methylamine and heated to 40 DEG C. in a closed pressure tube for 4 hours.

Po skončení zahrievania se ešte 6 hodin reakčná zmes mieša. Po skončení reakcie sauvolněním uzávěru odpaří prebytočný metylamín a k zvyšku sa přidá 45 až 50 ml etanolu asuspenzia sa 10 minút povarí. Po ochladení sa odsaje biely kryštalický l-metyl-6-amíno-5--metylamínouracil (2,8 g, 79,4 %) s t. t. 225 až 230 °C. Příklad 2After heating, the reaction mixture was stirred for 6 hours. After completion of the reaction, the excess methylamine is evaporated by loosening the cap and 45 to 50 ml of ethanol are added to the residue and boiling for 10 minutes. After cooling, white crystalline 1-methyl-6-amino-5-methylaminouracil (2.8 g, 79.4%), mp 225-230 ° C, is suctioned off. Example 2

Zmes 4,4 g l-metyl-6-amíno-5-brómuracilu (0,02 M) a 20 ml bezvodého metylamínu sa miešav uzavretej aparatúre pri teplote 20 °C 24 hodin. Odpaří sa prebytočný metylamín, tuhý zvyšoksa rozpustí v 15 ml vody prídavkom 1,5 až 2 ml kyseliny octovéj. Přidá sa aktivně uhlie,přefiltruje a číry roztok sa vyzráža vodným amoniakom. Vypadnutý l-metyl-6-amíno-5-metylamíno-uracil sa odsaje a vysuší. Výťažok 2,91 g.A mixture of 4.4 g of 1-methyl-6-amino-5-bromouracil (0.02 M) and 20 mL of anhydrous methylamine was stirred under a sealed apparatus at 20 ° C for 24 hours. Excess methylamine is evaporated, the solid residue is dissolved in 15 ml of water by addition of 1.5 to 2 ml of acetic acid. Charcoal is added, filtered and the clear solution is precipitated with aqueous ammonia. The precipitated 1-methyl-6-amino-5-methylamino-uracil is filtered off with suction and dried. Yield 2.91 g.

Claims (1)

3 265783 Příklad 3 10 g l-metyl-6-amíno-5-brómuracilu (0,045 M) a 30 ml bezvodého metylamínu sa zahrievalo na teplotu 70 °C 4 hodiny v uzatvorenej trubici za miešenia. Po spracovaní surověj reakčnej zmesi po oddestilovaní metylamínu etanolom sa získalo 6,5 g bieleho kryštaliokého produktu (84 %) s t. t. 225 až 230 °C. Přiklad 4 Analogicky ako v příklade 1, s tým, že k reakčnej zmesi sa přidá 0,4 g jodidu draselné-ho - výťažok 2,8 g. Příklad 5 5 g l-metyl-6-amino-5-brómuracilu a 15 ml bezvodého metylamínu a 0,1 g CuCl2 sa zahrievana teplotu 40 °C počas 4 hodin. Prebytočný metylamin sa odpaří, přidá sa 50 ml etanolu apřefiltruje sa. Získá sa 3,7 g produktu. PREDMET VYNÁLEZU SpSsob přípravy l-metyl-5-metylamíno-6-amínouracilu vzorca I OEXAMPLE 3 10 g of 1-methyl-6-amino-5-bromouracil (0.045 M) and 30 ml of anhydrous methylamine were heated to 70 DEG C. for 4 hours in a sealed tube with stirring. After working up the crude reaction mixture after distilling off the methylamine with ethanol, 6.5 g of a white crystalline product (84%) were obtained, m.p. 225-230 ° C. Example 4 Analogously to Example 1, 0.4 g of potassium iodide was added to the reaction mixture to yield 2.8 g. Example 5 5 g of 1-methyl-6-amino-5-bromouracil and 15 ml anhydrous methylamine and 0.1 g CuCl 2 are heated at 40 ° C for 4 hours. Excess methylamine is evaporated, 50 ml of ethanol is added and filtered. 3.7 g of product are obtained. OBJECT OF THE INVENTION Preparation of 1-methyl-5-methylamino-6-aminouracil of Formula IO ch3 /1/ z l-metyl-5-bróm-6-amínouracilu vzorca IIch3 / 1/1-methyl-5-bromo-6-aminouracil of formula II /11/ a metylamínu vyznačený tým, že reakcia sa prevádza v přebytku kvapalného bezvodého metylamínupri molárnom pomere metylamín:uráčil vzorca II = 4:1 až 50:1.And / or methylamine, characterized in that the reaction is carried out in an excess of liquid anhydrous methylamine with a methylamine molar ratio of the formula II = 4: 1 to 50: 1.
CS878786A 1987-12-03 1987-12-03 Preparation of 1-methyl-5-methylamino-6-aminouracil CS265783B1 (en)

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