CH310722A - Process for the production of a new Schiff base. - Google Patents
Process for the production of a new Schiff base.Info
- Publication number
- CH310722A CH310722A CH310722DA CH310722A CH 310722 A CH310722 A CH 310722A CH 310722D A CH310722D A CH 310722DA CH 310722 A CH310722 A CH 310722A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- diamino
- pyrimidine
- schiff base
- new
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 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
- 150000001875 compounds Chemical class 0.000 claims description 5
- -1 5 - (p - acetaminobenzalaminomethyl) - 2,4 - diamino - pyrimidine Chemical compound 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- 229940075930 picrate Drugs 0.000 claims description 3
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- SKLUWKYNZNXSLX-UHFFFAOYSA-N 4-Acetamidobenzaldehyde Chemical compound CC(=O)NC1=CC=C(C=O)C=C1 SKLUWKYNZNXSLX-UHFFFAOYSA-N 0.000 description 1
- GSCPVFNKSWRDMO-UHFFFAOYSA-N 5-(aminomethyl)pyrimidine-2,4-diamine Chemical compound NCC1=CN=C(N)N=C1N GSCPVFNKSWRDMO-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 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
- 238000002360 preparation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium 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
- C07D239/48—Two nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung einer neuen Schiffachen Base. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung einer neuen Sehiffsehen Base, welches dadurch gekenn zeichnet ist, dass man auf 2,4-Diamino-5- aminometliyl-pyrimidin eine das Radikal der Formel
EMI0001.0005
liefernde Verbindung einwirken lässt.
Als das Radikal der obigen Formel liefernde Verbin dungen seien genannt: p-Aeetamino-benz- aldeliyd, p-Acetamino-benzaldehydacetale oder -diaeylderivate oder p-Acetamino-benzalhalo- genide.
Das so erhaltene 5-(p-Acetaininobenzal- aminomethy 1) - 2,4 - diamino - pyrimidin, das wahrscheinlich wenigstens in Lösung im ('.leieligewicht mit der Ringform 2-Amino-\?'- p - aeetaminophenyl -1',2',3',4'-tetrahydropyr- imido-(5',6':5,4)-pyrimidin steht, schmilzt bei 196-1971' unter Zersetzung. Das Pikrat der Verbindung zersetzt sich ab 214 .
Das Ver fahrensprodukt soll als Chemotherapeuticum und als Zwischenprodukt Verwendung fin den.
<I>Beispiel:</I> Zu einer Lösung von 12,9g Natrium in 500 em3 abs. Methanol werden 46 g 2,4-Di- i amino -5-aminomethyl <B>-</B> pyrimidin-trihycli#ochlo- rid gegeben, das Ganze kurz zum Sieden er hitzt, gekühlt und mit. einer Lösung von 30 g p-Acetamino-benzaldehyd in 500 cm3 abs. Me- thanol vermischt.
Man kocht 15 Minuten,-p- stilliert den Methanol im Vakuum ab, versetzt den Rückstand mit 750 cm3 Wasser und kühlt unter Schütteln auf 0 . Das ausgefallene Pro dukt wird abgesaugt und aus Wasser umkri stallisiert. Man erhält so 39 g, das sind 74 /o der Theorie, der bei 196-197 unter Zerset zung schmelzenden p-Acetamino-benzalv erbin- dung von 2,4-Diamino-5-aminomethyl-pyrimi- din, Das Pikrat der Base zersetzt sich ab 214 .
Process for the production of a new shipping base. The subject of the present patent is a process for the preparation of a new Sehiffsehen base, which is characterized in that one has the radical of the formula on 2,4-diamino-5-aminometliyl-pyrimidine
EMI0001.0005
supplying compound can act.
The following compounds which provide the radical of the above formula may be mentioned: p-acetaminobenzaldelide, p-acetaminobenzaldehyde acetals or diaeyl derivatives or p-acetaminobenzalhalides.
The 5- (p-Acetaininobenzal- aminomethy 1) - 2,4 - diamino - pyrimidine thus obtained, which is probably at least in solution in the ('.leieligewicht with the ring form 2-Amino - \?' - p - aeetaminophenyl -1 ', 2 ', 3', 4'-tetrahydropyrimido (5 ', 6': 5.4) pyrimidine, melts with decomposition between 196 and 1971. The picrate of the compound decomposes from 214 onwards.
The process product is intended to be used as a chemotherapeutic agent and as an intermediate product.
<I> Example: </I> To a solution of 12.9g sodium in 500 em3 abs. To methanol, 46 g of 2,4-di-amino -5-aminomethyl pyrimidine-trihyclic chloride are added, the whole thing is briefly heated to the boil, cooled and with. a solution of 30 g of p-acetaminobenzaldehyde in 500 cm3 of abs. Methanol mixed.
It is boiled for 15 minutes, the methanol is distilled off in vacuo, 750 cm3 of water are added to the residue and the mixture is cooled to 0 while shaking. The precipitated product is suctioned off and recrystallized from water. This gives 39 g, that is 74% of theory, of the p-acetaminobenzal compound of 2,4-diamino-5-aminomethylpyrimidine, the picrate of the base, which melts at 196-197 with decomposition decomposes from 214.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH310722T | 1952-06-27 | ||
| CH309034T | 1955-08-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH310722A true CH310722A (en) | 1955-10-31 |
Family
ID=25735556
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH310722D CH310722A (en) | 1952-06-27 | 1952-06-27 | Process for the production of a new Schiff base. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH310722A (en) |
-
1952
- 1952-06-27 CH CH310722D patent/CH310722A/en unknown
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