PL134157B1 - Process for preparing 2-methylthio-4-aminopyrimidine - Google Patents
Process for preparing 2-methylthio-4-aminopyrimidine Download PDFInfo
- Publication number
- PL134157B1 PL134157B1 PL23253181A PL23253181A PL134157B1 PL 134157 B1 PL134157 B1 PL 134157B1 PL 23253181 A PL23253181 A PL 23253181A PL 23253181 A PL23253181 A PL 23253181A PL 134157 B1 PL134157 B1 PL 134157B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- methylthio
- ch3s
- amino
- preparation
- Prior art date
Links
- HGGXLEAHOVIYKT-UHFFFAOYSA-N 2-methylsulfanylpyrimidin-4-amine Chemical compound CSC1=NC=CC(N)=N1 HGGXLEAHOVIYKT-UHFFFAOYSA-N 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims description 13
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000006114 decarboxylation reaction Methods 0.000 claims description 3
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- QINRQIZOBCQKAZ-UHFFFAOYSA-N ethyl 4-amino-2-methylsulfanylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(SC)N=C1N QINRQIZOBCQKAZ-UHFFFAOYSA-N 0.000 description 3
- SNNHLSHDDGJVDM-UHFFFAOYSA-N ethyl 4-chloro-2-methylsulfanylpyrimidine-5-carboxylate Chemical class CCOC(=O)C1=CN=C(SC)N=C1Cl SNNHLSHDDGJVDM-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- VZOPVKZLLGMDDG-UHFFFAOYSA-N 1-oxido-4-phenylpyridin-1-ium Chemical compound C1=C[N+]([O-])=CC=C1C1=CC=CC=C1 VZOPVKZLLGMDDG-UHFFFAOYSA-N 0.000 description 2
- AOBVZYNKWONVRH-UHFFFAOYSA-N 4-amino-2-methylsulfanylpyrimidine-5-carboxylic acid Chemical compound CSC1=NC=C(C(O)=O)C(N)=N1 AOBVZYNKWONVRH-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 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
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- DJDDYWYYTKNZPM-UHFFFAOYSA-N 2-amino-1,3-dioxane-4,6-dione Chemical compound NC1OC(=O)CC(=O)O1 DJDDYWYYTKNZPM-UHFFFAOYSA-N 0.000 description 1
- DOGLQBAGFNPSQG-UHFFFAOYSA-N 2-methylsulfanyl-1H-pyrimidin-2-ol Chemical compound CSC1(O)NC=CC=N1 DOGLQBAGFNPSQG-UHFFFAOYSA-N 0.000 description 1
- MZSQIZRESVBKIM-UHFFFAOYSA-N 2-methylsulfanylpyridin-4-amine Chemical compound CSC1=CC(N)=CC=N1 MZSQIZRESVBKIM-UHFFFAOYSA-N 0.000 description 1
- UYHSQVMHSFXUOA-UHFFFAOYSA-N 2-methylthiouracil Chemical compound CSC1=NC=CC(O)=N1 UYHSQVMHSFXUOA-UHFFFAOYSA-N 0.000 description 1
- ZJKIBABOSPFBNO-UHFFFAOYSA-N 3-hydroxyprop-2-enoic acid Chemical compound OC=CC(O)=O ZJKIBABOSPFBNO-UHFFFAOYSA-N 0.000 description 1
- 241000272814 Anser sp. Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- HIDSGWORWBEEQY-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)-3-hydroxybutanedioate Chemical compound CCOC=C(C(=O)OCC)C(O)C(=O)OCC HIDSGWORWBEEQY-UHFFFAOYSA-N 0.000 description 1
- NINSPLAPBBAHEW-UHFFFAOYSA-N ethyl 3-hydroxyprop-2-enoate Chemical compound CCOC(=O)C=CO NINSPLAPBBAHEW-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229960004979 fampridine Drugs 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- NNBBQNFHCVVQHZ-UHFFFAOYSA-N methyl carbamimidothioate;sulfuric acid Chemical compound CSC(N)=N.OS(O)(=O)=O NNBBQNFHCVVQHZ-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 229960001732 pipemidic acid Drugs 0.000 description 1
- JOHZPMXAZQZXHR-UHFFFAOYSA-N pipemidic acid Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CN=C1N1CCNCC1 JOHZPMXAZQZXHR-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 229960004444 piromidic acid Drugs 0.000 description 1
- RCIMBBZXSXFZBV-UHFFFAOYSA-N piromidic acid Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CN=C1N1CCCC1 RCIMBBZXSXFZBV-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU202080A YU41728B (en) | 1980-08-11 | 1980-08-11 | Process for preparing 2-methylthio-4-amino pyrimidines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL232531A1 PL232531A1 (cs) | 1982-04-26 |
| PL134157B1 true PL134157B1 (en) | 1985-07-31 |
Family
ID=25556514
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL23253181A PL134157B1 (en) | 1980-08-11 | 1981-08-07 | Process for preparing 2-methylthio-4-aminopyrimidine |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5759875A (cs) |
| CS (1) | CS220345B2 (cs) |
| DD (1) | DD201895A5 (cs) |
| ES (1) | ES504501A0 (cs) |
| PL (1) | PL134157B1 (cs) |
| PT (1) | PT73498B (cs) |
| SU (1) | SU999968A3 (cs) |
| YU (1) | YU41728B (cs) |
-
1980
- 1980-08-11 YU YU202080A patent/YU41728B/xx unknown
-
1981
- 1981-08-03 ES ES504501A patent/ES504501A0/es active Granted
- 1981-08-07 PL PL23253181A patent/PL134157B1/pl unknown
- 1981-08-10 PT PT7349881A patent/PT73498B/pt unknown
- 1981-08-10 SU SU813324050A patent/SU999968A3/ru active
- 1981-08-11 DD DD23252981A patent/DD201895A5/de unknown
- 1981-08-11 JP JP56124826A patent/JPS5759875A/ja active Pending
- 1981-08-11 CS CS603081A patent/CS220345B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5759875A (en) | 1982-04-10 |
| PL232531A1 (cs) | 1982-04-26 |
| PT73498A (en) | 1981-09-01 |
| PT73498B (en) | 1982-10-28 |
| ES8303359A1 (es) | 1983-02-01 |
| YU41728B (en) | 1987-12-31 |
| ES504501A0 (es) | 1983-02-01 |
| YU202080A (en) | 1983-02-28 |
| DD201895A5 (de) | 1983-08-17 |
| SU999968A3 (ru) | 1983-02-23 |
| CS220345B2 (en) | 1983-03-25 |
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