PL164076B1 - Method of obtaining 2-phenyl-4/4'-hydrophenylamino/-6-methyl-5-hydroxymethyl-pyrimidine - Google Patents
Method of obtaining 2-phenyl-4/4'-hydrophenylamino/-6-methyl-5-hydroxymethyl-pyrimidineInfo
- Publication number
- PL164076B1 PL164076B1 PL28435190A PL28435190A PL164076B1 PL 164076 B1 PL164076 B1 PL 164076B1 PL 28435190 A PL28435190 A PL 28435190A PL 28435190 A PL28435190 A PL 28435190A PL 164076 B1 PL164076 B1 PL 164076B1
- Authority
- PL
- Poland
- Prior art keywords
- phenyl
- methyl
- pyrimidine
- hydroxymethyl
- chlorophenylamino
- Prior art date
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Sposóbwytwarzania2-fenylo-4(4’-chlorofenyloamino)-6-metylo-5-hydroksymetylo -pirymidyny o wzorze 1, znamienny tym, że ester etylowy kwasu 2-fenylo-4(4’-chlorofenyloamino)-6-metylo-5-pirymidyno-karbo ksylowego o wzorze 2 redukuje się przy pomocy glinowodorku litu w bezwodnym tetrahydrofuranie.Method to produce 2-phenyl-4 (4'-chlorophenylamino) -6-methyl-5-hydroxymethyl - pyrimidines of formula 1, characterized in that 2-phenyl-4 (4'-chlorophenylamino) -6-methyl-5-pyrimidine-carbohydrate ethyl ester xyl of formula II is reduced with Lithium aluminum hydride in anhydrous tetrahydrofuran.
Description
Przedmiotem wynalazku jest sposób wytwarzania 2-fenylo-4-(4’-chlorofenyloamino)-6metylo-5-hydroksymetylo-pirymidyny o wzorze 1, wykazującej aktywność biologiczną.The subject of the invention is a process for the preparation of 2-phenyl-4- (4'-chlorophenylamino) -6-methyl-5-hydroxymethyl-pyrimidine of formula 1, showing biological activity.
Według wynalazku sposób wytwarzania 2-fenylo-4(4’-chlorofenyloamino)-6-metylo-5hydroksymetylo-pirymidyny o wzorze 1 polega na tym, że ester etylowy kwasu 2-fenylo-4(4’chlorofenyloamino)-6-metylo-5-pirymidyno-karboksylowego o wzorze 2 redukuje się przy pomocy glinowodorku litu w bezwodnym tetrahydrofuranie.According to the invention, the process for the preparation of 2-phenyl-4- (4'-chlorophenylamino) -6-methyl-5-hydroxymethyl-pyrimidine of the formula I consists in 2-phenyl-4- (4'-chlorophenylamino) -6-methyl-5-acid ethyl ester the pyrimidine carboxylic acid of formula II is reduced with lithium aluminum hydride in anhydrous tetrahydrofuran.
Związek wytworzony sposobem według wynalazku wykazuje silne działanie immunotropowe na humoralną i komórkową odpowiedź immunologiczną, określoną aktywnością preparatu na produkcję przeciwciał 19S i 7S, stymulującą wytwarzanie leukocytów A i B.The compound according to the invention shows a strong immunotropic effect on the humoral and cellular immune response, determined by the activity of the preparation on the production of 19S and 7S antibodies, stimulating the production of A and B leukocytes.
Aktywność biologiczną sprawdzono in vitro i in vivo. Działanie immunostymulujące in vivo sprawdzono na zwierzętach doświadczalnych za pomocą testu Jernego na stabilność humoralną oraz w teście GvH na aktywność komórkową.The biological activity was checked in vitro and in vivo. The in vivo immunostimulatory effect was verified in experimental animals using the Jerny test for humoral stability and the GvH test for cellular activity.
Przedmiot wynalazku jest przedstawiony w przykładzie wykonania.The subject of the invention is presented in an exemplary embodiment.
Przykład. 4g (0,01 mola) estru etylowego kwasu 2-fenylo- 4(4’-chlorofenyloamino)6-metylo-5-pirymidynokarboksylowego rozpuszcza się w 20,0 ml bezwodnego tetrahydrofuranu i dodaje niewielkimi porcjami intensywnie mieszając 0,5 g (0,01 mola) glinowodorku litu. Po upływie 1 godziny całość wylewa się na lód. Wytrącone gliniany odsącza się, a przesącz estrakuje trzykrotnie 50,0 ml chloroformu. Wyciągi chloroformowe łączy się i osusza siarczanem rtęci. Po odsączeniu znad siarczanu rtęci ekstrakt zagęszcza się pod zmniejszonym ciśnieniem do sucha i krystalizuje z acetonu, uzyskując 2,9 g kremowo-żółtych kryształów o temperaturze topnienia 432-434 K, z wydajnością równą 82,2% wydajności teoretycznej.Example. 4 g (0.01 mol) of 2-phenyl-4- (4'-chlorophenylamino) 6-methyl-5-pyrimidinecarboxylic acid ethyl ester was dissolved in 20.0 ml of anhydrous tetrahydrofuran and added in small portions, intensively stirring 0.5 g (0 01 mole) of lithium aluminum hydride. After 1 hour, it was poured onto ice. The precipitated clays are filtered off and the filtrate is trapped three times with 50.0 ml of chloroform. The chloroform extracts are combined and dried with mercury sulfate. After filtering over the mercury sulphate, the extract is concentrated to dryness under reduced pressure and recrystallized from acetone to give 2.9 g of cream-yellow crystals, m.p. 432-434 K, 82.2% of theory.
164 076164 076
Wzór 2Formula 2
Departament Wydawnictw UP RP. Nakład 90 egz. Cena 10 000 złPublishing Department of the UP RP. Circulation of 90 copies. Price: PLN 10,000
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL28435190A PL164076B1 (en) | 1990-03-15 | 1990-03-15 | Method of obtaining 2-phenyl-4/4'-hydrophenylamino/-6-methyl-5-hydroxymethyl-pyrimidine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL28435190A PL164076B1 (en) | 1990-03-15 | 1990-03-15 | Method of obtaining 2-phenyl-4/4'-hydrophenylamino/-6-methyl-5-hydroxymethyl-pyrimidine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL284351A1 PL284351A1 (en) | 1991-09-23 |
| PL164076B1 true PL164076B1 (en) | 1994-06-30 |
Family
ID=20050644
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL28435190A PL164076B1 (en) | 1990-03-15 | 1990-03-15 | Method of obtaining 2-phenyl-4/4'-hydrophenylamino/-6-methyl-5-hydroxymethyl-pyrimidine |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL164076B1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8455489B2 (en) * | 2003-11-10 | 2013-06-04 | Exelixis, Inc. | Substituted pyrimidine compositions and methods of use |
-
1990
- 1990-03-15 PL PL28435190A patent/PL164076B1/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8455489B2 (en) * | 2003-11-10 | 2013-06-04 | Exelixis, Inc. | Substituted pyrimidine compositions and methods of use |
Also Published As
| Publication number | Publication date |
|---|---|
| PL284351A1 (en) | 1991-09-23 |
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