CH310726A - Process for the production of a new Schiff base. - Google Patents
Process for the production of a new Schiff base.Info
- Publication number
- CH310726A CH310726A CH310726DA CH310726A CH 310726 A CH310726 A CH 310726A CH 310726D A CH310726D A CH 310726DA CH 310726 A CH310726 A CH 310726A
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- pyrimidine
- production
- benzylmercapto
- schiff base
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000002262 Schiff base Substances 0.000 title 1
- 150000004753 Schiff bases Chemical class 0.000 title 1
- -1 5- (p-acetaminobenzalaminomethyl) -2-benzylmercapto-4-amino-6-methyl-pyrimidine Chemical compound 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- CKPWQTFDXKRFLG-UHFFFAOYSA-N 5-(aminomethyl)-2-benzylsulfanyl-6-methylpyrimidin-4-amine Chemical compound NC1=C(CN)C(C)=NC(SCC=2C=CC=CC=2)=N1 CKPWQTFDXKRFLG-UHFFFAOYSA-N 0.000 claims description 2
- 239000002246 antineoplastic 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- SKLUWKYNZNXSLX-UHFFFAOYSA-N 4-Acetamidobenzaldehyde Chemical compound CC(=O)NC1=CC=C(C=O)C=C1 SKLUWKYNZNXSLX-UHFFFAOYSA-N 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 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 einer neuen Schiffsehen Base. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung einer neuen Schiffsehen Base, welches dadurch gekenn zeichnet ist, da.ss man auf 2-Benzylmercapto- 4-amino - 5 - aminomethyl - 6 - methyl - py rimidin eine das Radikal der Formel
EMI0001.0008
liefernde Verbindung einwirken lässt.
Als das Radikal der obigen Formel liefernde Verbin dungen seien genannt: p-Acetamino-benzalde- hyd, p-Acetamino-benzaldehydacetale oder -di- acylderivate oder p-Acetamino-benzalhaloge- nide.
Das so erhaltene 5-(p-Aeetaminobenzal- amin omethyl) -2-benzy lmercapto-4-amino-6-me- thyl.-pyrimidin, das wahrscheinlich wenigstens in Lösung im Gleichgewicht mit der Ring form 2-Benzylmercapto-6-methyl-2'-p-acet- aminophenyl - 1',2',3',4' - tetrahydropyrimido- (5',6' :
5,4)-pyrimidin steht, schmilzt bei 133 bis 7.35 . Das Verfahrensprodukt soll als Chemotherapeuticum und als Zwisehenpro- clukt Verwendung finden.
<I>Beispiel:</I> Eine Lösung von 20 g 2-Benzylmereapto-4- a mino - 5 - aminomethyl - 6-znethyl-pyrimidin in Methanol wird mit einer Lösung von 1.2,5 g p-Acetainino-benzaldehyd in 200 em3 abs. Me thanol vermischt.
Man kocht 15 Minuten, de stilliert den Methanol im Vakuum ab, versetzt den Rückstand mit 200 em3 Wasser und kühlt unter Schütteln auf 0 . Das ausgefallene Pro dukt wird abgesaugt und aus Äthanol umkri- stallisiert. Man erhält so 19 g, das sind 61% der Theorie,
der bei 133-135 schmelzenden p-Acetamino-benzalverbindung von 2-Benzyl- mercapto -4- amino -.5 - aminomethyl - 6- methyl- pyrimidin.
Method of manufacturing a new marine base. The subject of the present patent is a process for the preparation of a new Schiffsehen base, which is characterized by the fact that 2-benzylmercapto-4-amino-5-aminomethyl-6-methyl-pyrimidine is a radical of the formula
EMI0001.0008
supplying compound can act.
The following compounds which provide the radical of the above formula may be mentioned: p-acetaminobenzaldehyde, p-acetaminobenzaldehyde acetals or -diacyl derivatives or p-acetaminobenzalhalogenides.
The 5- (p-ethaminobenzalamine omethyl) -2-benzyl mercapto-4-amino-6-methyl-pyrimidine obtained in this way, which is probably at least in solution in equilibrium with the ring form 2-benzylmercapto-6-methyl -2'-p-acet-aminophenyl - 1 ', 2', 3 ', 4' - tetrahydropyrimido- (5 ', 6':
5,4) pyrimidine, melts at 133 to 7.35. The process product is intended to be used as a chemotherapeutic agent and as an intermediate product.
<I> Example: </I> A solution of 20 g of 2-benzylmereapto-4- a mino - 5 - aminomethyl - 6-methyl-pyrimidine in methanol is mixed with a solution of 1.2.5 g of p-acetainino-benzaldehyde in 200 em3 abs. Methanol mixed.
The mixture is boiled for 15 minutes, the methanol is distilled off in vacuo, the residue is treated with 200 cubic meters of water and cooled to 0 while shaking. The precipitated product is filtered off with suction and recrystallized from ethanol. You get 19 g, that's 61% of theory,
the p-acetaminobenzal compound of 2-benzyl mercapto -4-amino -.5-aminomethyl-6-methyl-pyrimidine, which melts at 133-135.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH310726T | 1952-06-27 | ||
| CH309034T | 1955-08-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH310726A true CH310726A (en) | 1955-10-31 |
Family
ID=25735560
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH310726D CH310726A (en) | 1952-06-27 | 1952-06-27 | Process for the production of a new Schiff base. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH310726A (en) |
-
1952
- 1952-06-27 CH CH310726D patent/CH310726A/en unknown
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