CH308210A - Process for the preparation of a new pyrimidine derivative. - Google Patents
Process for the preparation of a new pyrimidine derivative.Info
- Publication number
- CH308210A CH308210A CH308210DA CH308210A CH 308210 A CH308210 A CH 308210A CH 308210D A CH308210D A CH 308210DA CH 308210 A CH308210 A CH 308210A
- Authority
- CH
- Switzerland
- Prior art keywords
- pyrimidine derivative
- preparation
- pyrimidine
- aminomethyl
- new pyrimidine
- Prior art date
Links
- 150000003230 pyrimidines Chemical class 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 3
- 239000002246 antineoplastic agent Substances 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 229940127089 cytotoxic agent Drugs 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- HMWDLVRYRPUQOL-UHFFFAOYSA-N 5-(aminomethyl)pyrimidin-2-amine Chemical compound NCC1=CN=C(N)N=C1 HMWDLVRYRPUQOL-UHFFFAOYSA-N 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- -1 lithium aluminum hydride Chemical compound 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- VYDHBDPZNLVELI-UHFFFAOYSA-N 4-amino-2-methylsulfanylpyrimidine-5-carbonitrile Chemical compound CSC1=NC=C(C#N)C(N)=N1 VYDHBDPZNLVELI-UHFFFAOYSA-N 0.000 description 1
- YWAYJPPPWVEGAQ-UHFFFAOYSA-N 5-(aminomethyl)-2-methylsulfanylpyrimidin-4-amine Chemical compound CSC1=NC=C(CN)C(N)=N1 YWAYJPPPWVEGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines neuen Pyrimidinderivates. Gegenstand des vorliegenden Patentes bil det ein Verfahren zur Herstellung eines neuen Pyrimidinderivates, welches dadurch gekenn zeichnet ist, dass man ein Pyrimidinderivat der Formel
EMI0001.0006
in welcher X einen durch Reduktion in die Aminomethylgrnppe überführbaren Rest be deutet, mit einem Reduktionsmittel behandelt.
Der Rest X kann beispielsweise in einer Cyanogruppe oder einer Carbamidogruppe be stehen. Im ersteren Falle kann die Cyano- gruppe leicht mit Raney-Nickel und Wasser stoff vorteilhaft in alkoholischem. Ammoniak als Lösungsmittel reduziert werden oder auch mit Lithiumaluminiumhydrid in Äther, Tetra- hydrofuran usw.
Die Carbamidogruppe kann mit Hilfe von Alkali-aluminium- oder -borhydriden in die Aminomethylgruppe übergeführt werden.
Das so erhaltene 2 - Methylmercapto - 4- amino-5-aminomethyl-pyrimidin bildet farb lose Kristalle, die bei 96-98 schmelzen. Es soll als Chemotherapeutikum und als Zwi schenprodukt verwendet werden.
<I>Beispiel:</I> 50 g 2 - Methylmercapto - 4 - amino - 5 - cyan- pyrimidin in 500 em3 Tetrahydrofuran wer- den unter Eiskühlung und Rühren in eine Lösung von 40 g Lithiilmaluminiumhydrid in 500 em3 Tetrahydrofuran eingetropft. Man turbiniert das Ganze einige Stunden und lässt dann 2.4 Stunden stehen. Nach dem Versetzen der Reaktionslösung mit Wasser wird filtriert und das Filtrat alkalisch gemacht.
Das Aus gefallene wird nach dem Trocknen aus Benzol umkristallisiert. Man erhält so das 2-Benzyl- mercapto-4-amino-5-aminomethyl-pyrimidin in farblosen, bei 96-98 schmelzenden Kristal len.
Process for the preparation of a new pyrimidine derivative. The subject of the present patent bil det a process for the preparation of a new pyrimidine derivative, which is characterized in that a pyrimidine derivative of the formula
EMI0001.0006
in which X denotes a radical which can be converted into the aminomethyl group by reduction, treated with a reducing agent.
The radical X can be, for example, in a cyano group or a carbamido group. In the former case the cyano group can easily be mixed with Raney nickel and hydrogen, advantageously in alcoholic. Ammonia can be reduced as a solvent or with lithium aluminum hydride in ether, tetrahydrofuran etc.
The carbamido group can be converted into the aminomethyl group with the aid of alkali aluminum or borohydrides.
The 2-methylmercapto-4-amino-5-aminomethyl-pyrimidine obtained in this way forms colorless crystals which melt at 96-98. It should be used as a chemotherapeutic agent and as an intermediate product.
Example: 50 g of 2-methylmercapto-4-amino-5-cyano-pyrimidine in 500 cubic meters of tetrahydrofuran are added dropwise to a solution of 40 g of lithium aluminum hydride in 500 cubic meters of tetrahydrofuran with ice-cooling and stirring. You turbine the whole thing for a few hours and then let it stand for 2.4 hours. After adding water to the reaction solution, it is filtered and the filtrate is made alkaline.
The precipitated is recrystallized from benzene after drying. The 2-benzyl mercapto-4-amino-5-aminomethyl-pyrimidine is thus obtained in colorless crystals which melt at 96-98.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH306509T | 1952-06-27 | ||
| CH308210T | 1952-06-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH308210A true CH308210A (en) | 1955-06-30 |
Family
ID=25735172
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH308210D CH308210A (en) | 1952-06-27 | 1952-06-27 | Process for the preparation of a new pyrimidine derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH308210A (en) |
-
1952
- 1952-06-27 CH CH308210D patent/CH308210A/en unknown
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