SU448178A1 - Method for preparing 5-deoxy-5-fluoro-methyl mercaptopurine riboside - Google Patents
Method for preparing 5-deoxy-5-fluoro-methyl mercaptopurine ribosideInfo
- Publication number
- SU448178A1 SU448178A1 SU1714801A SU1714801A SU448178A1 SU 448178 A1 SU448178 A1 SU 448178A1 SU 1714801 A SU1714801 A SU 1714801A SU 1714801 A SU1714801 A SU 1714801A SU 448178 A1 SU448178 A1 SU 448178A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- deoxy
- fluoro
- preparing
- mercaptopurine riboside
- riboside
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 6
- 229960001428 mercaptopurine Drugs 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000008223 ribosides Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
Description
1one
Изобретение относитс к способу получени нового соединени , которое может найти применение в фармацевтической промышленности .This invention relates to a process for the preparation of a novel compound that can be used in the pharmaceutical industry.
Широко известен способ получени тиоэфиров из меракаптидов натри или кали и алкилирующих агентов.A method of producing thioesters from sodium or potassium meracaptids and alkylating agents is widely known.
Использование известного способа привело к получению 5-дезокси-5-фтор-6-метилмеркаптопуринрибозида формулы:Using a known method resulted in a 5-deoxy-5-fluoro-6-methylmercaptopurine riboside formula:
ОН ОНOH OH
обладающего ценной биологической активностью .possessing valuable biological activity.
Способ заключаетс в том, что 5-дезокси-5фтор-2 ,3-ди-0 - диацетил-6-меркаитопуринрибозид подвергают взаимодействию с йодистым метилом в щелочной среде с последующим выделением целевого продукта известным способом . При этом во врем реакции метилировани происходит одновременное отщепление обеих ацетильных групп радикала рибозида. Пример. 210 мг 6-меркапто-9-(2,3-диацетил-5-дезокси - 5 - фтор- (3-D - рибофуранозил )-пурина раствор ют в 2,5 мл метанола и воды (соотнощение 2: 1) и провод т реакцию между полученной смесью и 1,07 мл йодистого метила. Затем в смесь по капл м добавл ют 0,554 мл NaOH и в течение часа перемешивают при комнатной температуре, после чего обрабатывают уксусной кислотой до рН 5. Затем раствор концентрируют в вакууме до сухого состо ни .The method consists in that 5-deoxy-5-fluoro-2, 3-di-0-diacetyl-6-merkaitopurinriboside is reacted with methyl iodide in an alkaline medium, followed by isolation of the target product in a known manner. In this case, during the methylation reaction, both acetyl groups of the riboside radical are simultaneously cleaved. Example. 210 mg of 6-mercapto-9- (2,3-diacetyl-5-deoxy-5-fluoro- (3-D-ribofuranosyl) -purine) is dissolved in 2.5 ml of methanol and water (ratio 2: 1) and wire The reaction between the mixture obtained and 1.07 ml of methyl iodide is then added dropwise to the mixture 0.554 ml of NaOH and stirred for an hour at room temperature, then treated with acetic acid to pH 5. The solution is then concentrated in vacuo to dryness. neither
Полученный продукт очищают на колонке силикагел (100 г), использу в качестве растворител смесь хлороформа и 96%-ного этанола (соотношение 9:1). В результате получают 152 мг (89% теории) стекловидного продукта , из которого после выдерживани в эфире выпадают кристаллы. После сушки в вакууме при 75°С, т. пл. полученного продукта составл ет 163-164°С. Путем перекристаллизации из метанола т. пл. можно повысить до 164-165°С. +173,5 (с 1,2 воды), ультрафиолетовый спектр (метанол) Ямакс. 282,5 и 217,5 nm, плечо при 291 nm, 243 пш. 34The product obtained is purified on a silica gel column (100 g) using a mixture of chloroform and 96% ethanol (9: 1 ratio) as a solvent. As a result, 152 mg (89% of theory) of a vitreous product are obtained, from which crystals are left to stand in the ether. After drying in vacuum at 75 ° C, so pl. the resulting product is 163-164 ° C. By recrystallization from methanol, m.p. can be increased to 164-165 ° C. +173.5 (with 1.2 water), ultraviolet spectrum (methanol) Yamax. 282.5 and 217.5 nm, shoulder at 291 nm, 243 psh. 34
Предмет изобретени тил-6-меркаптопуринрибозид подвергают взаСпособ получени 5-дезокси-5-фтор-6-ме- среде с последующим выделением целевого тилмеркаптопуринрибозида, отличающий-продукта известным способом,The subject matter of til-6-mercaptopurine riboside is subjected to a mutual method for preparing 5-deoxy-5-fluoro-6-medium followed by isolation of the desired tylmercaptopurine riboside, the distinguishing product in a known manner,
с тем, что 5-дезокси-5-фтор-2,3-ди-0-диаце- 5so that 5-deoxy-5-fluoro-2,3-di-0-diacene-5
448178 448178
имодесйтвию с йодистым метилом в щелочнойmethyl iodide in alkaline
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1714801A SU448178A1 (en) | 1971-11-16 | 1971-11-16 | Method for preparing 5-deoxy-5-fluoro-methyl mercaptopurine riboside |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1714801A SU448178A1 (en) | 1971-11-16 | 1971-11-16 | Method for preparing 5-deoxy-5-fluoro-methyl mercaptopurine riboside |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU448178A1 true SU448178A1 (en) | 1974-10-30 |
Family
ID=20493126
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1714801A SU448178A1 (en) | 1971-11-16 | 1971-11-16 | Method for preparing 5-deoxy-5-fluoro-methyl mercaptopurine riboside |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU448178A1 (en) |
-
1971
- 1971-11-16 SU SU1714801A patent/SU448178A1/en active
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