SU485597A3 - Способ получени производных -триазол/1,5-а/-пиримидинов - Google Patents
Способ получени производных -триазол/1,5-а/-пиримидиновInfo
- Publication number
- SU485597A3 SU485597A3 SU1447118A SU1447118A SU485597A3 SU 485597 A3 SU485597 A3 SU 485597A3 SU 1447118 A SU1447118 A SU 1447118A SU 1447118 A SU1447118 A SU 1447118A SU 485597 A3 SU485597 A3 SU 485597A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- triazole
- methyl
- oxo
- pyrimidine
- propyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- -1 amino compound Chemical class 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- PKWIYNIDEDLDCJ-UHFFFAOYSA-N guanazole Chemical compound NC1=NNC(N)=N1 PKWIYNIDEDLDCJ-UHFFFAOYSA-N 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- HBNYJWAFDZLWRS-UHFFFAOYSA-N ethyl isothiocyanate Chemical compound CCN=C=S HBNYJWAFDZLWRS-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 125000005059 halophenyl group Chemical group 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000003884 phenylalkyl group Chemical group 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 101150012842 BIO2 gene Proteins 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- GKHPIMSWLLQUMS-UHFFFAOYSA-N ethyl n'-ethylcarbamimidothioate;hydrobromide Chemical compound Br.CCSC(N)=NCC GKHPIMSWLLQUMS-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/14—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4362768 | 1968-09-13 | ||
| GB2226669 | 1969-05-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU485597A3 true SU485597A3 (ru) | 1975-09-25 |
Family
ID=26255820
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1447118A SU485597A3 (ru) | 1968-09-13 | 1969-09-02 | Способ получени производных -триазол/1,5-а/-пиримидинов |
| SU1365596A SU511001A3 (ru) | 1968-09-13 | 1969-09-02 | Способ получени производных -триазоло/1,5- / пиримидинов |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1365596A SU511001A3 (ru) | 1968-09-13 | 1969-09-02 | Способ получени производных -триазоло/1,5- / пиримидинов |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3689488A (https=) |
| JP (1) | JPS517677B1 (https=) |
| BE (1) | BE738830A (https=) |
| CH (2) | CH522666A (https=) |
| DE (1) | DE1946315C2 (https=) |
| DK (1) | DK137498B (https=) |
| ES (1) | ES371509A1 (https=) |
| FR (1) | FR2018077B1 (https=) |
| IE (1) | IE33549B1 (https=) |
| IL (1) | IL32992A (https=) |
| NL (1) | NL162651C (https=) |
| SE (3) | SE373584B (https=) |
| SU (2) | SU485597A3 (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4046552A (en) * | 1976-04-15 | 1977-09-06 | Imperial Chemical Industries Limited | Herbicidal compositions of bipyridylium quaternary salts and emetic amounts of s-triazolo pyrimidine derivatives |
| GB1507407A (en) * | 1976-04-15 | 1978-04-12 | Ici Ltd | Herbicidal compositions |
| IE46306B1 (en) * | 1977-02-11 | 1983-05-04 | Ici Ltd | Safeguarded toxic chemical compositions containing an emetic |
| US4223031A (en) * | 1978-05-05 | 1980-09-16 | Mead Johnson & Company | Azolopyrimidinones |
| US4491587A (en) * | 1978-05-05 | 1985-01-01 | Mead Johnson & Company | Tetrazole derivatives |
| US4497814A (en) * | 1982-08-16 | 1985-02-05 | Schering Corporation | 2-(Pyridinyl)-1,2,4-triazolo[1,5-a]pyrimidines and derivatives useful in increasing cardiac contractility |
| US4532242A (en) * | 1983-05-02 | 1985-07-30 | Riker Laboratories, Inc. | Substituted triazolo[4,3-c]pyrimidines |
| US4528288A (en) * | 1983-05-02 | 1985-07-09 | Riker Laboratories, Inc. | Substituted triazolo[1,5-c]pyrimidines |
| US6570014B1 (en) * | 2002-04-30 | 2003-05-27 | Sinon Corporation | Process for preparing triazolopyrimidine derivatives |
| EP1359149B1 (en) * | 2002-05-03 | 2008-12-31 | Sinon Corporation, Yang, Wen-Bin | Process for preparing triazolopyrimidine derivatives |
| US7662831B2 (en) * | 2006-07-27 | 2010-02-16 | Wyeth Llc | Tetracyclic indoles as potassium channel modulators |
| US7601856B2 (en) * | 2006-07-27 | 2009-10-13 | Wyeth | Benzofurans as potassium ion channel modulators |
| CN107602563B (zh) * | 2017-09-19 | 2019-05-17 | 马鞍山德鸿生物技术有限公司 | 百草枯催吐剂三氮唑嘧啶酮的制备方法 |
| CN107602565B (zh) * | 2017-09-20 | 2020-03-31 | 浙江大学 | 2-氨基-6-甲基-[1，2，4]-三唑并[1，5-a]嘧啶-5-酮的合成方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB897870A (en) * | 1959-06-15 | 1962-05-30 | Ici Ltd | s-triazolo[2, 3-c]pyrimidine derivatives |
| US3202512A (en) * | 1962-02-23 | 1965-08-24 | Eastman Kodak Co | Photographic silver halide emulsions stabilized with tetrazaindene compounds |
| GB1070243A (en) * | 1964-07-15 | 1967-06-01 | Smith Kline French Lab | S-triazolopyrimidones, their preparation and compositions containing them |
| GB999381A (en) * | 1964-08-20 | 1965-07-28 | Kodak Ltd | New substituted tetrazaindene compounds and their uses in photography |
-
1969
- 1969-08-12 IE IE1134/69A patent/IE33549B1/xx unknown
- 1969-08-14 US US850221A patent/US3689488A/en not_active Expired - Lifetime
- 1969-08-27 DK DK458669AA patent/DK137498B/da not_active IP Right Cessation
- 1969-09-02 SU SU1447118A patent/SU485597A3/ru active
- 1969-09-02 SU SU1365596A patent/SU511001A3/ru active
- 1969-09-12 SE SE6912601A patent/SE373584B/xx unknown
- 1969-09-12 DE DE1946315A patent/DE1946315C2/de not_active Expired
- 1969-09-12 FR FR696931200A patent/FR2018077B1/fr not_active Expired
- 1969-09-12 BE BE738830D patent/BE738830A/xx not_active IP Right Cessation
- 1969-09-12 SE SE7216480A patent/SE377461B/xx unknown
- 1969-09-12 SE SE7216479A patent/SE377460B/xx unknown
- 1969-09-12 NL NL6913907.A patent/NL162651C/xx not_active IP Right Cessation
- 1969-09-12 JP JP44072676A patent/JPS517677B1/ja active Pending
- 1969-09-12 IL IL32992A patent/IL32992A/en unknown
- 1969-09-13 ES ES371509A patent/ES371509A1/es not_active Expired
- 1969-09-15 CH CH1390469A patent/CH522666A/de not_active IP Right Cessation
- 1969-09-15 CH CH118872A patent/CH523270A/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| SE377460B (https=) | 1975-07-07 |
| JPS517677B1 (https=) | 1976-03-10 |
| DE1946315C2 (de) | 1985-05-15 |
| NL162651B (nl) | 1980-01-15 |
| US3689488A (en) | 1972-09-05 |
| FR2018077B1 (https=) | 1973-01-12 |
| SU511001A3 (ru) | 1976-04-15 |
| ES371509A1 (es) | 1971-11-01 |
| IL32992A0 (en) | 1969-11-30 |
| FR2018077A1 (https=) | 1970-05-29 |
| CH523270A (de) | 1972-05-31 |
| DK137498C (https=) | 1978-08-28 |
| IE33549L (en) | 1970-03-13 |
| NL6913907A (https=) | 1970-03-17 |
| IL32992A (en) | 1972-08-30 |
| NL162651C (nl) | 1980-06-16 |
| IE33549B1 (en) | 1974-08-07 |
| SE373584B (sv) | 1975-02-10 |
| BE738830A (https=) | 1970-03-12 |
| SE377461B (https=) | 1975-07-07 |
| DE1946315A1 (de) | 1970-03-19 |
| DK137498B (da) | 1978-03-13 |
| CH522666A (de) | 1972-06-30 |
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