CH304553A - Process for the preparation of a pyrimidine derivative. - Google Patents
Process for the preparation of a pyrimidine derivative.Info
- Publication number
- CH304553A CH304553A CH304553DA CH304553A CH 304553 A CH304553 A CH 304553A CH 304553D A CH304553D A CH 304553DA CH 304553 A CH304553 A CH 304553A
- Authority
- CH
- Switzerland
- Prior art keywords
- dione
- ethyl
- reduction
- phenyl
- carried out
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- 150000003230 pyrimidines Chemical class 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 5
- 238000002844 melting Methods 0.000 claims description 5
- 230000008018 melting Effects 0.000 claims description 5
- DQMZLTXERSFNPB-UHFFFAOYSA-N primidone Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NCNC1=O DQMZLTXERSFNPB-UHFFFAOYSA-N 0.000 claims description 5
- 239000007868 Raney catalyst Substances 0.000 claims description 4
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 4
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 230000001773 anti-convulsant effect Effects 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- DKYBVKMIZODYKL-UHFFFAOYSA-N 1,3-diazinane Chemical group C1CNCNC1 DKYBVKMIZODYKL-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims 3
- 101100495769 Caenorhabditis elegans che-1 gene Proteins 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- VZZXPTLMLZOKJX-UHFFFAOYSA-N 2-ethoxy-5-ethyl-5-phenyl-1,3-diazinane-4,6-dione Chemical compound O=C1NC(OCC)NC(=O)C1(CC)C1=CC=CC=C1 VZZXPTLMLZOKJX-UHFFFAOYSA-N 0.000 description 1
- MFQUYXWVXJXLSZ-UHFFFAOYSA-N 5-ethyl-2-methoxy-5-phenyl-1,3-diazinane-4,6-dione Chemical compound C(C)C1(C(NC(NC1=O)OC)=O)C1=CC=CC=C1 MFQUYXWVXJXLSZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYECOJGRJDOGPP-UHFFFAOYSA-N Ethylurea Chemical compound CCNC(N)=O RYECOJGRJDOGPP-UHFFFAOYSA-N 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- -1 ethoxy-5-phenyl-5-ethyl-tetrahydropyrimidine-4,6-dione Chemical compound 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung eines Pyrimidinderivates. Die vorliegende Erfindung bezieht sich auf ein Verfahren zur Herstellung eines Py- rimidinderivates, nämlich des 5-Phenyl-5-äthyl- hexahydropyrimidin-4,6-dions, das die Eigen s sehaften eines Anticonvulsivtuns aufweist und die folgende Strukturformel besitzt
EMI0001.0009
Gemäss der vorliegenden Erfindung wird (las genannte Pyrimidinderivat nach einem Verfahren hergestellt, bei welchem eine Ver bindung der Formel:
EMI0001.0011
in welcher R einen Kohlenwasserstoffrest be zeichnet, z.
B. einen Alkyl-, Alkenyl- oder Aralkylrest, reduziert wird, wobei im Verlaufe der Reduktion die Gruppe -0R vom Hexa- hydropyrimidinring abgespalten wird.
5 - Phenyl-5-äthyl-hexahydropyr imidin-4,6 - dion ist eine farblose kristalline Substanz vom Schmelzpunkt 281 C, die starke antikonvul sive Eigenschaften besitzt.
Die Reduktion wird z. B. in alkalischem, jedoch vorzugsweise in neutralem Medium aus- geführt. Die katalytische Hydrierung, insbe sondere die Reduktion mittels wasserstoff haltigen Raney-Nickelpräparaten, beispiels weise des im Journal of the American Che- mical Society , 1948, 70, 695, unter der Be zeichnung W5 beschriebenen Präparates, hat sich als geeignet erwiesen.
Es kann angenommen werden, sei jedoch nur als Erklärung erwähnt, dass die Reduk tion über die Bildung eines Zwischenproduk tes der Formel:
EMI0001.0032
in welcher R die oben definierte Bedeutung besitzt, erfolgt.
Die Erfindung wird in den folgenden Bei spielen, in welchen die Teile gewichtsmässig angegeben sind, näher erläutert.
<I>Beispiel 1:</I> 2 Teile 2-Methoxy-5-phenyl-5-äthyl-tetra- hydropyrimidin-4,6-dion, 100 Teile Äthanol und 10 Teile Raney-Nickel W5 (hergestellt nach der im Journal of the American Chemi- cal Society , 1948, 70, 695 beschriebenen Me thode) werden zusammen während 2 Stunden unter Rückfluss erhitzt.
Das Gemisch wird dann heiss filtriert, worauf das Filtrat auf ein kleines Volumen eingeengt, abgekühlt und erneut filtriert wird. Der feste Rückstand be steht aus 5-Phenyl-5-äthyl-hexahydropyrimidin- 4,6-dion vom Smp. 281 C.
<I>Beispiel</I> 29: 2 Teile 2-Äthoxy-5-phenyl-5-äthyl-tetra- hydropyrimidin-4,6-dion, 150 Teile Äthanol und 15 Teile Raney-Nickel W5 werden zusam men während 3 Stunden unter Rückfluss er hitzt. Das Gemisch wird dann filtriert, wor auf das Filtrat auf ein kleines Volumen ein geengt, abgekühlt und erneut filtriert wird. Der feste Rückstand besteht aus 5-Phenyl-5- äthyl-hexahydropyrimidin-4,6-dion vom Smp. 281 C.
Das als Ausgangsmaterial verwendete 2 Äthoxy-5-phenyl-5-äthyl-tetrahydropyrimidin- 4,6-dion vom Smp. 104 bis 105 C kann durch Kondensation von Plienyläthylmalonylchlorid mit Äthylisoharnstoff erhalten werden.
Process for the preparation of a pyrimidine derivative. The present invention relates to a process for the preparation of a pyrimidine derivative, namely 5-phenyl-5-ethylhexahydropyrimidine-4,6-dione, which has the properties of an anticonvulsant and has the following structural formula
EMI0001.0009
According to the present invention, the pyrimidine derivative mentioned is produced by a process in which a compound of the formula:
EMI0001.0011
in which R denotes a hydrocarbon radical, e.g.
B. an alkyl, alkenyl or aralkyl radical, is reduced, the group -0R being split off from the hexahydropyrimidine ring in the course of the reduction.
5 - Phenyl-5-ethyl-hexahydropyrimidine-4,6 - dione is a colorless crystalline substance with a melting point of 281 C, which has strong anticonvulsant properties.
The reduction is z. B. carried out in an alkaline, but preferably in a neutral medium. The catalytic hydrogenation, in particular the reduction by means of hydrogen-containing Raney nickel preparations, for example the preparation described in the Journal of the American Chemical Society, 1948, 70, 695, under the designation W5, has proven to be suitable.
It can be assumed, but should only be mentioned as an explanation, that the reduction via the formation of an intermediate product of the formula:
EMI0001.0032
in which R has the meaning defined above, takes place.
The invention is explained in more detail in the following examples, in which the parts are indicated by weight.
<I> Example 1: </I> 2 parts of 2-methoxy-5-phenyl-5-ethyl-tetrahydropyrimidine-4,6-dione, 100 parts of ethanol and 10 parts of Raney nickel W5 (prepared according to the in Journal of the American Chemical Society, 1948, 70, 695 described method) are refluxed together for 2 hours.
The mixture is then filtered hot, whereupon the filtrate is concentrated to a small volume, cooled and filtered again. The solid residue consists of 5-phenyl-5-ethyl-hexahydropyrimidine-4,6-dione of melting point 281 C.
<I> Example </I> 29: 2 parts of 2-ethoxy-5-phenyl-5-ethyl-tetrahydropyrimidine-4,6-dione, 150 parts of ethanol and 15 parts of Raney nickel W5 are mixed together for 3 hours under reflux he heats. The mixture is then filtered and the filtrate is concentrated to a small volume, cooled and filtered again. The solid residue consists of 5-phenyl-5-ethyl-hexahydropyrimidine-4,6-dione with a melting point of 281 C.
The 2 ethoxy-5-phenyl-5-ethyl-tetrahydropyrimidine-4,6-dione with a melting point of 104 to 105 ° C. can be obtained by condensation of plienylethylmalonyl chloride with ethylisourea.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB304553X | 1951-04-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH304553A true CH304553A (en) | 1955-01-15 |
Family
ID=10307956
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH304553D CH304553A (en) | 1951-04-23 | 1952-04-21 | Process for the preparation of a pyrimidine derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH304553A (en) |
-
1952
- 1952-04-21 CH CH304553D patent/CH304553A/en unknown
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