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 PDFInfo
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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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- Prior art keywords
- amino
- dipiperonylfuro
- formamide
- pyrimidine
- preparation
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- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 title claims description 7
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims abstract description 20
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims abstract description 11
- STDCIOHTJAFQEU-UHFFFAOYSA-N NC=1OC(=C(C=1C#N)CC1=CC2=C(C=C1)OCO2)CC1=CC2=C(C=C1)OCO2 Chemical compound NC=1OC(=C(C=1C#N)CC1=CC2=C(C=C1)OCO2)CC1=CC2=C(C=C1)OCO2 STDCIOHTJAFQEU-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000009835 boiling Methods 0.000 claims description 2
- 240000000260 Typha latifolia Species 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 238000010992 reflux Methods 0.000 abstract description 3
- 238000003756 stirring Methods 0.000 abstract description 3
- 238000004949 mass spectrometry Methods 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003217 anti-cancerogenic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- -1 pyrimidine compound Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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:
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:
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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS401980A CS209610B1 (en) | 1980-06-06 | 1980-06-06 | 4-amino-5,6-dipiperonylfuro /2,3-b/ pyridimine and method of preparation thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS401980A CS209610B1 (en) | 1980-06-06 | 1980-06-06 | 4-amino-5,6-dipiperonylfuro /2,3-b/ pyridimine and method of preparation thereof |
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| Publication Number | Publication Date |
|---|---|
| CS209610B1 true CS209610B1 (en) | 1981-12-31 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS401980A CS209610B1 (en) | 1980-06-06 | 1980-06-06 | 4-amino-5,6-dipiperonylfuro /2,3-b/ pyridimine and method of preparation thereof |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS209610B1 (en) |
-
1980
- 1980-06-06 CS CS401980A patent/CS209610B1/en unknown
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