CS209610B1 - 4-amino-5,6-dipiperonylfuro /2,3-b/ pyridimine and method of preparation thereof - Google Patents

4-amino-5,6-dipiperonylfuro /2,3-b/ pyridimine and method of preparation thereof Download PDF

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CS209610B1
CS209610B1 CS401980A CS401980A CS209610B1 CS 209610 B1 CS209610 B1 CS 209610B1 CS 401980 A CS401980 A CS 401980A CS 401980 A CS401980 A CS 401980A CS 209610 B1 CS209610 B1 CS 209610B1
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amino
dipiperonylfuro
formamide
pyrimidine
preparation
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CS401980A
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Czech (cs)
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Josef Prousek
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Josef Prousek
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Abstract

Účelom vynálezu je riešenie přípravy novej zlúčeniny 4-araino-5,6-dipiperonylfuro- -/2,3-b/pyrimidinu. Tento sa připravuje z 2-amino-3-kyano-4,5-dipiperonylfuránu a formamidu pri teplote nad 100 °C, za miešania alebo pri teplote refluxu formamidu. Struktura zlúčeniny je dokázaná IČ, UV, ^H-NMR a hmotovou spektroskop iou. Štruktúrny vzorec pripravenej zlúčeniny jeThe purpose of the invention is to provide a preparation solution of the new compound 4-araino-5,6-dipiperonylurea - [2,3-b] pyrimidine. This is being prepared from 2-amino-3-cyano-4,5-dipiperonylfuran and formamide at a temperature above 100 ° C with stirring or at the reflux temperature of formamide. The structure of the compound is proved by IR, UV, @ 1 H-NMR and mass spectroscopy. Structural the formula of the compound prepared is

Description

(54) 4amino-5.6-dipiperonylfúro(2,3-b)pyrimidín a spósob jeho přípravy(54) 4 amino-5,6-dipiperonylfuro (2,3-b) pyrimidine and a process for its preparation

Účelom vynálezu je riešenie přípravy novej zlúčeniny 4-araino-5,6-dipiperonylfuro-/2,3-b/pyrimidinu. Tento sa připravuje z 2-amino-3-kyano-4,5-dipiperonylfuránu a formamidu pri teplote nad 100 °C, za miešania alebo pri teplote refluxu formamidu. Struktura zlúčeniny je dokázaná IČ, UV, ^H-NMR a hmotovou spektroskop iou. Štruktúrny vzorec pripravenej zlúčeniny jeIt is an object of the present invention to provide a novel 4-araino-5,6-dipiperonylfuro [2,3-b] pyrimidine compound. This is prepared from 2-amino-3-cyano-4,5-dipiperonylfuran and formamide at a temperature above 100 ° C, with stirring or at the reflux temperature of the formamide. The structure of the compound is shown by IR, UV, 1 H-NMR and mass spectroscopy. The structural formula of the prepared compound is

Vynález sa týká 4-amino-5,6-dipiperony1furo/2,3-b/pyrimidínu a spósobu jeho přípravy.The invention relates to 4-amino-5,6-dipiperonylfuro [2,3-b] pyrimidine and a process for its preparation.

Popísané je, že 4-amino-5,6-di substituované furopyrimidíny a ich analogy sa syntetizujú z hladiska hladania biologicky účinných preparátov hlavně s antikancerogennou účinnostou. 4-amino-5,6-dipiperonylfuro/2,3-b/pyrimidín ako nová východzia surovina pre celú radu syntéz nových furopyrimidínov a dalších heterocyklov na jeho báze připravených, nebol doteraz připrav ený .It is described that 4-amino-5,6-di substituted furopyrimidines and their analogs are synthesized from the viewpoint of searching for biologically active preparations mainly with anticancerogenic activity. 4-Amino-5,6-dipiperonylfuro [2,3-b] pyrimidine as a new starting material for a variety of syntheses of new furopyrimidines and other heterocycles prepared on its basis has not been prepared.

Tieto nedostatky v podstatnej miere odstraňuje vynález týkajúci sa 4-amino-5,6-dipiperony 1 f ur o- / 2 , 3 - b /py r im id i nu a spósobu jeho přípravy, ktorého podstata spočívá v reakcii 2-amino-3-kyano-4,5-dipiperonylfuránu s formamidom pri teplote nad 100 °C za miešania, alebo pri teplote refluxu formamidu.These drawbacks are substantially eliminated by the invention relating to 4-amino-5,6-dipiperone-1-uro [2,3-b] pyrimidine and to a process for its preparation which is based on the reaction of 2-amino- 3-cyano-4,5-dipiperonylfuran with formamide at a temperature above 100 ° C with stirring or at the reflux temperature of the formamide.

Cyklizačná reakcia prebieha podlá nasledujúcej schéray.The cyclization reaction is carried out according to the following scheme.

Sposob přípravy 4-amino-5,6-dipiperonylfuro-/2,3-b/pyrimidinu podlá vynálezu je výhodný z hladiska dobrých výtažkov, čistoty získanej látky, dostupnosti východiskových produktov a krátkosti reakcného času.The process of preparing 4-amino-5,6-dipiperonylfuro [2,3-b] pyrimidine according to the invention is advantageous in terms of good yields, purity of the obtained material, availability of starting products and short reaction time.

Predmet vynálezu je ilustrovaný na nás1edujúcich príkladoch, bez toho, aby sa iba na tieto v stahoval .The subject matter of the invention is illustrated by the following examples, without being limited to these.

PřikladlHe did

Roztok 0,8 g /2,3 mmol/ 2-amino-3-kyano-4,5-dipiperony1furánu v 15 ml formamidu sa pomaly zahřeje k varu a refluxuje 30 minút. Po ochladení sa potom reakčná zmes vyleje do ladovej vody a surový produkt sa odsaje. Prekryšta1 izovanim z dimety1su1foxidu alebo nadbytku etylalkoholu, metyla1 koholu sa získajú berfarebné kryštáliky. Získá sa. 0,75 g 4-amino-5,6-dipiperonylfuro-/2,3-b/pyrimidínu s teplotou topenia 272 °C v 87,2%-nom výtažku.A solution of 0.8 g (2.3 mmol) of 2-amino-3-cyano-4,5-dipiperonyl furan in 15 ml of formamide is slowly heated to boiling and refluxed for 30 minutes. After cooling, the reaction mixture is then poured into ice water and the crude product is filtered off with suction. Recrystallization from dimethylsulfoxide or an excess of ethyl alcohol and methyl alcohol gives the color crystals. It is obtained. 0.75 g of 4-amino-5,6-dipiperonylfuro [2,3-b] pyrimidine, m.p. 272 DEG C., 87.2% yield.

Příklad 2Example 2

Do 80 ml variaceho sa formamidu sa přidá 3,48 g /0,01 mol/ 2-amino-3-kyano-4,5-dipiperonylfuránu po častiach, přibližné za 10 minút. Po.ochladení sa zmes vyleje na drtený lad. Surový produkt sa odsaje a prekryšta 1 izuje z d im e t y 1 su 1 f ox id u . Získá sa 3,2 g produktu s teplotou topenia 271 až 273 °C, čo představuje 86,5%-ný výtažok.To 80 ml of the variation formamide was added 3.48 g (0.01 mol) of 2-amino-3-cyano-4,5-dipiperonylfuran in portions over approximately 10 minutes. After cooling, the mixture was poured onto crushed ice. The crude product is filtered off with suction and recrystallized from dimethylsulfoxide. 3.2 g of product are obtained, m.p. 271 DEG-273 DEG C., which is 86.5% yield.

Získaný 4“amino-5,6-dipipercnylfuro,'2,3-b/pyrimidín je látka štruktúrneho vzorcaThe obtained 4-amino-5,6-dipipercyllfuro, 2,3-b / pyrimidine is a compound of the structural formula

ktorej sumárny vzorec je a molekulová hmotnost je 3 75 , 3 2 .whose total formula is and the molecular weight is 3 75, 3 2.

2096 1 02096 1 0

Eleraentáťna analýza poskytla tieto výsledky:Eleraentate analysis gave the following results:

Z C Z C Z H Z H Z N Z N vypočítané množstvo calculated amount 64,00 64.00 3,49 3.49 11,19 11.19 nájdené množstvo amount found 64,21 64.21 3,51 3.51 11,10 11.10

štruktúra 4-amino-5,6-dipiperonylfuro/2,3-b/pyrimidínu bola dokázaná spektrálnými metodami a to IČ, UV, 1H-NMR a hmotovou spektroskópiou.structure of 4-amino-5,6-dipiperonylfuro / 2,3-b / pyrimidine was evidenced by the spectral methods and IR, UV, 1 H NMR and mass spectral data.

UV spektrá boli namerané na přístroji Specord UV-VIS /Zeiss Jena/, ako rozpúštadlo bol použitý metylalkohol. Látka vykazuje nasledujúce absorbčné pásy:UV spectra were recorded on a Specord UV-VIS instrument (Zeiss Jena) using methanol as solvent. The substance has the following absorption bands:

max max = 207 = 207 nm nm log log = 4,79 = 4.79 max max = 261 = 261 nm nm log log - 4,04 - 4,04 max max = 298 = 298 nm nm log log = 4,36 = 4.36 max max = 328 = 328 nm nm log log = 4,54 = 4.54 max max = 340 = 340 nm nm log log - 4,41 - 4,41

IČ spektra boli namerané na přístroji UR-20 /Zeiss, Jena/ KBr technikou. IČ spektrum vykazuje tieto charakteristické pásy:IR spectra were recorded on a UR-20 / Zeiss, Jena / KBr instrument. The IR spectrum shows the following characteristic bands:

461 cm*1, 3 380 cm-1, 3 288 cm-’, 2 900 cm-1, 1 650 cm-1, 1 592 cm'1, 1 503 cm-1, 1 480 cm-1,461 cm * 1, 3380 cm -1, 3288 cm - ', 2900 cm -1, 1650 cm -1, 1592 cm -1, 1503 cm -1, 1480 cm -1,

448 cm-1, 1 240 cm'1, 1 230 cm1, 1 040 cm'1, 987 cm-1, 933 cm-1.448 cm -1, 1240 cm -1, 1230 cm 1, 1040 cm -1, 987 cm -1, 933 cm 1st

1H-NMR spektrum bolo namerané na přístroji TESLA BS 487 C /80 MHz/. NMR spektrum bolo získané meraníra látky v hexadeuterodimetylsu1foxidu pri 25 °C za použitia hexametyldisiloxánu ako interného standardu. V tabulke sú uvedené hodnoty chemických posuvov v jednotkách p. p. m. 1 H-NMR spectrum was recorded on a TESLA BS 487 C (80 MHz) instrument. The NMR spectrum was obtained by measuring the substance in hexadeuterodimethylsulfoxide at 25 ° C using hexamethyldisiloxane as an internal standard. The table shows the chemical shift values in ppm

Claims (2)

PREDMET VYNÁLEZUOBJECT OF THE INVENTION 1. 4-amino-5,6-dípiperonylfuro/2,3-b/pyr imid ín vzorcaA 4-amino-5,6-dipiperonylfuro [2,3-b] pyrimidine of the formula 2. Sposob přípravy 4-amino-5,6-dipiperonylfuro/2,3-b/pyrimidinu podlá bodu 1, vyznačený tým, že 2-amino-3-kyano-4,5-dipiper ony 1furán vzorca reaguje s formamidom vzorca v rozmedzí teplot 100 °C až do teploty varu formamidu.2. A process for the preparation of 4-amino-5,6-dipiperonylfuro [2,3-b] pyrimidine according to claim 1, wherein the 2-amino-3-cyano-4,5-dipiperonylfuran is reacted with the formamide of formula (I). between 100 ° C and the boiling point of formamide. Severoprafia. n. p.. závod 7. Most,Severoprafia. n. p. plant 7. Most,
CS401980A 1980-06-06 1980-06-06 4-amino-5,6-dipiperonylfuro /2,3-b/ pyridimine and method of preparation thereof CS209610B1 (en)

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