CS209610B1 - 4-amino-5, 5-dipiperonylfuro (2,3-b) pyrimidine and a method for its preparation - Google Patents

4-amino-5, 5-dipiperonylfuro (2,3-b) pyrimidine and a method for its preparation 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
pyrimidine
dipiperonylfuro
preparation
formamide
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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 solve the preparation of a new compound 4-araino-5,6-dipiperonylfuro- /2,3-b/pyrimidine. 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 formamide. The structure of the compound is proven by infrared, UV, ^H-NMR and mass spectroscopy. The structural formula of the prepared compound is

Description

(54) 4amino-5.6-dipiperonylfúro(2,3-b)pyrimidín a spósob jeho přípravy(54) 4amino-5,6-dipiperonylfuro(2,3-b)pyrimidine and method 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 jeThe purpose of the invention is to solve the preparation of a new compound 4-araino-5,6-dipiperonylfuro-/2,3-b/pyrimidine. 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 formamide. The structure of the compound is proven by IR, UV, ^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 analogues are synthesized from the point of view of searching for biologically active preparations mainly with anticancer activity. 4-amino-5,6-dipiperonylfuro/2,3-b/pyrimidine as a new starting material for a whole range of syntheses of new furopyrimidines and other heterocycles prepared on its basis, or prepared so far.

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 shortcomings are largely eliminated by the invention relating to 4-amino-5,6-dipiperone 1 furo-/2,3-b/pyrimidine and the method of its preparation, the essence of which consists in 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 formamide.

Cyklizačná reakcia prebieha podlá nasledujúcej schéray.The cyclization reaction proceeds 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 method of preparation of 4-amino-5,6-dipiperonylfuro-/2,3-b/pyrimidine according to the invention is advantageous in terms of good yields, purity of the substance obtained, 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 of the invention is illustrated in the following examples, without being limited to these.

PřikladlExample

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-dipiperone-1-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. By precrystallizing from dimethylsulphoxide or an excess of ethyl alcohol, methylcohol, multi-colored crystals are obtained. It will be obtained. 0.75 g of 4-amino-5,6-dipiperonylfuro-[2,3-b]pyrimidine with a melting point of 272 °C in 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.3.48 g (0.01 mol) of 2-amino-3-cyano-4,5-dipiperonylfuran was added portionwise over approximately 10 minutes to 80 mL of boiling formamide. After cooling, the mixture is poured over crushed ice. The crude product is filtered off with suction and recrystallized from dimer oxide. 3.2 g of product with a melting point of 271 to 273 °C is obtained, which represents an 86.5% yield.

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

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

2096 1 02096 1 0

Eleraentáťna analýza poskytla tieto výsledky:Eleraental analysis provided the following results:

Z C From C Z H From H Z N From N vypočítané množstvo calculated amount 64,00 64.00 3,49 3.49 11,19 11.19 nájdené množstvo quantity 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.the structure of 4-amino-5,6-dipiperonylfuro/2,3-b/pyrimidine was proven by spectral methods, namely IR, UV, 1 H-NMR and mass spectroscopy.

UV spektrá boli namerané na přístroji Specord UV-VIS /Zeiss Jena/, ako rozpúštadlo bol použitý metylalkohol. Látka vykazuje nasledujúce absorbčné pásy:UV spectra were measured on a Specord UV-VIS device /Zeiss Jena/, methyl alcohol was used as a solvent. The substance shows 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 measured on a UR-20 instrument /Zeiss, Jena/ using the KBr technique. 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 , 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 ,

448 cm-1, 1 240 cm'1, 1 230 cm1, 1 040 cm'1, 987 cm-1, 933 cm-1.448 cm -1 , 1 240 cm' 1 , 1 230 cm 1 , 1 040 cm' 1 , 987 cm- 1 , 933 cm- 1 .

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 measured 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 values of chemical shifts in units of 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, 5-dipiperonylfuro (2,3-b) pyrimidine and a method for its preparation CS209610B1 (en)

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