CH308212A - Process for the preparation of a new pyrimidine derivative. - Google Patents
Process for the preparation of a new pyrimidine derivative.Info
- Publication number
- CH308212A CH308212A CH308212DA CH308212A CH 308212 A CH308212 A CH 308212A CH 308212D A CH308212D A CH 308212DA CH 308212 A CH308212 A CH 308212A
- Authority
- CH
- Switzerland
- Prior art keywords
- pyrimidine derivative
- preparation
- new pyrimidine
- pyrimidine
- aminomethyl
- 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
- -1 2-mercapto-4-amino-5-aminomethyl-pyrimidine Chemical compound 0.000 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
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 229940044683 chemotherapy drug Drugs 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WCGUHTXQXJRNRJ-UHFFFAOYSA-N 6-amino-2-sulfanylidene-1h-pyrimidine-5-carbonitrile Chemical compound NC=1NC(=S)N=CC=1C#N WCGUHTXQXJRNRJ-UHFFFAOYSA-N 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
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000000463 material Substances 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (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
EMI0001.0005
in welcher X einen durch Reduktion in die Aminomethylgruppe überführbaren Rest be deutet, mit einem Reduktionsmittel behandelt.
Der Rest X kann beispielsweise in einer Cyanogruppe oder einer Carbamidogruppe be stehen. Diese können mit Hilfe von Alkali aluminium- oder -borhydriden in die Amino- methylgruppeübergeführt werden.
Das so erhaltene 2-Mercapto-4-amino-5- aminomethyl-pyrimidin bildet farblose Kri stalle, die bei 220" unter Zersetzung schmel zen. Es soll als Chemotherapeutikum und als Zwischenprodukt verwendet werden.
Beispiel: 18 g 2-Mercapto-4-amino-5-cyan-pyrimidin in 250 cm3 Tetrahydrofuran werden zu einer Lösung von 16 g Lithiumaluminiumhydrid in 250 cm3 Tetrahydrofuran gegeben. Man rührt das Ganze einige Stunden und lässt dann 24 Stunden stehen. Anschliessend giesst man auf Wasser, versetzt mit Essigsäure; filtriert und dampft ein. Den Rückstand stellt man leicht alkalisch und kristallisiert das Ungelöste aus Wasser um.
Man erhält so das 2-Mercapto-4- amino-5-aminomethyl-pyrimidin in farblosen, bei 220 unter Zersetzung schmelzenden Kri stallen.
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
EMI0001.0005
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. These can be converted into the aminomethyl group with the help of alkali aluminum or borohydrides.
The 2-mercapto-4-amino-5-aminomethyl-pyrimidine obtained in this way forms colorless crystals which melt at 220 "with decomposition. It is intended to be used as a chemotherapeutic agent and as an intermediate.
Example: 18 g of 2-mercapto-4-amino-5-cyano-pyrimidine in 250 cm3 of tetrahydrofuran are added to a solution of 16 g of lithium aluminum hydride in 250 cm3 of tetrahydrofuran. The whole thing is stirred for a few hours and then left to stand for 24 hours. It is then poured into water, and acetic acid is added; filtered and evaporated. The residue is made slightly alkaline and the undissolved material is recrystallized from water.
The 2-mercapto-4-amino-5-aminomethyl-pyrimidine is thus obtained in colorless crystals which melt at 220 with decomposition.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH306509T | 1952-06-27 | ||
| CH308212T | 1952-06-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH308212A true CH308212A (en) | 1955-06-30 |
Family
ID=25735174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH308212D CH308212A (en) | 1952-06-27 | 1952-06-27 | Process for the preparation of a new pyrimidine derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH308212A (en) |
-
1952
- 1952-06-27 CH CH308212D patent/CH308212A/en unknown
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