JPH052672B2 - - Google Patents
Info
- Publication number
- JPH052672B2 JPH052672B2 JP56116365A JP11636581A JPH052672B2 JP H052672 B2 JPH052672 B2 JP H052672B2 JP 56116365 A JP56116365 A JP 56116365A JP 11636581 A JP11636581 A JP 11636581A JP H052672 B2 JPH052672 B2 JP H052672B2
- Authority
- JP
- Japan
- Prior art keywords
- added
- water
- represented
- derivative
- aminopyrimidine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000005005 aminopyrimidines Chemical class 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 11
- NHMJSZPYDBDLPG-UHFFFAOYSA-N 2-nitrosopyrimidin-4-amine Chemical class NC1=CC=NC(N=O)=N1 NHMJSZPYDBDLPG-UHFFFAOYSA-N 0.000 claims description 8
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical class OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 claims description 3
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 235000010288 sodium nitrite Nutrition 0.000 description 11
- ANGDWNBGPBMQHW-UHFFFAOYSA-N methyl cyanoacetate Chemical compound COC(=O)CC#N ANGDWNBGPBMQHW-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 230000009935 nitrosation Effects 0.000 description 6
- 238000007034 nitrosation reaction Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- SWELIMKTDYHAOY-UHFFFAOYSA-N 2,4-diamino-6-hydroxypyrimidine Chemical compound NC1=CC(=O)N=C(N)N1 SWELIMKTDYHAOY-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 239000011343 solid material Substances 0.000 description 3
- HVMRLFSFHWCUCG-UHFFFAOYSA-N 2,6-diamino-5-nitroso-1h-pyrimidin-4-one Chemical compound NC1=NC(=O)C(N=O)=C(N)N1 HVMRLFSFHWCUCG-UHFFFAOYSA-N 0.000 description 2
- LNDZXOWGUAIUBG-UHFFFAOYSA-N 6-aminouracil Chemical compound NC1=CC(=O)NC(=O)N1 LNDZXOWGUAIUBG-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 2
- 208000013403 hyperactivity Diseases 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- ARHYKCFDDWXCTI-UHFFFAOYSA-N 2-cyano-2-nitrosoacetic acid Chemical class OC(=O)C(N=O)C#N ARHYKCFDDWXCTI-UHFFFAOYSA-N 0.000 description 1
- FLFZMCJIHCDWKG-UHFFFAOYSA-N 2-nitrosopyrimidine Chemical class O=NC1=NC=CC=N1 FLFZMCJIHCDWKG-UHFFFAOYSA-N 0.000 description 1
- YFYYRKDBDBILSD-UHFFFAOYSA-N 6-amino-2-sulfanylidene-1h-pyrimidin-4-one Chemical compound NC1=CC(=O)NC(=S)N1 YFYYRKDBDBILSD-UHFFFAOYSA-N 0.000 description 1
- UOWCFGBLAMCSFY-UHFFFAOYSA-N 6-amino-5-nitroso-2-sulfanylidene-1h-pyrimidin-4-one Chemical compound NC=1NC(=S)NC(=O)C=1N=O UOWCFGBLAMCSFY-UHFFFAOYSA-N 0.000 description 1
- DKPCSXFEWFSECE-UHFFFAOYSA-N 6-amino-5-nitrosopyrimidine-2,4-diol Chemical compound NC=1NC(=O)NC(=O)C=1N=O DKPCSXFEWFSECE-UHFFFAOYSA-N 0.000 description 1
- JEBHQJDMOHYNNN-UHFFFAOYSA-N CO.Cl.NC(=N)N Chemical compound CO.Cl.NC(=N)N JEBHQJDMOHYNNN-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229960000789 guanidine hydrochloride Drugs 0.000 description 1
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001042 pteridinyl group Chemical class N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 description 1
- HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56116365A JPS5818367A (ja) | 1981-07-27 | 1981-07-27 | ニトロソピリミジン誘導体の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56116365A JPS5818367A (ja) | 1981-07-27 | 1981-07-27 | ニトロソピリミジン誘導体の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5818367A JPS5818367A (ja) | 1983-02-02 |
| JPH052672B2 true JPH052672B2 (de) | 1993-01-13 |
Family
ID=14685154
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56116365A Granted JPS5818367A (ja) | 1981-07-27 | 1981-07-27 | ニトロソピリミジン誘導体の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5818367A (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH660589A5 (de) * | 1983-01-28 | 1987-05-15 | Lonza Ag | Verfahren zur herstellung von 2-substituierten 5-nitroso-4,6-diamino-pyrimidinen. |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2673204A (en) * | 1950-09-16 | 1954-03-23 | Wickhen Products Inc | Processes for the syntheses of leucopterin and the intermediates thereof and of 2, 4, 5-triamino-6-hydroxy pyrimidine sulfite and the alkali salts thereof |
-
1981
- 1981-07-27 JP JP56116365A patent/JPS5818367A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2673204A (en) * | 1950-09-16 | 1954-03-23 | Wickhen Products Inc | Processes for the syntheses of leucopterin and the intermediates thereof and of 2, 4, 5-triamino-6-hydroxy pyrimidine sulfite and the alkali salts thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5818367A (ja) | 1983-02-02 |
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