JPS627189B2 - - Google Patents
Info
- Publication number
- JPS627189B2 JPS627189B2 JP6625183A JP6625183A JPS627189B2 JP S627189 B2 JPS627189 B2 JP S627189B2 JP 6625183 A JP6625183 A JP 6625183A JP 6625183 A JP6625183 A JP 6625183A JP S627189 B2 JPS627189 B2 JP S627189B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- hydrochloric acid
- thioxopyrimidine
- methanol
- mmol
- 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
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 12
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 5
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical compound CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 2
- MBOCEPWYDNXEKN-UHFFFAOYSA-N 3,4-dihydro-1h-pyrimidine-2-thione Chemical compound S=C1NCC=CN1 MBOCEPWYDNXEKN-UHFFFAOYSA-N 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 7
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 2
- RJUNNVICUVQORF-UHFFFAOYSA-N 3-oxobutanamide;hydrochloride Chemical compound Cl.CC(=O)CC(N)=O RJUNNVICUVQORF-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 1
- DPSOJGVVUIDMDM-UHFFFAOYSA-N 4-phenyl-3,4-dihydro-1h-pyrimidine-2-thione Chemical compound N1C(=S)NC=CC1C1=CC=CC=C1 DPSOJGVVUIDMDM-UHFFFAOYSA-N 0.000 description 1
- -1 5- ethoxycarbonyl-6-methyl-4-substituted- 1,2,3,4-tetrahydro-2-oxopyrimidine Chemical class 0.000 description 1
- GKQDZJNUBAKTOW-UHFFFAOYSA-N 6-methyl-4-(4-nitrophenyl)-2-sulfanylidene-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=S)NC(C)=C(C(N)=O)C1C1=CC=C([N+]([O-])=O)C=C1 GKQDZJNUBAKTOW-UHFFFAOYSA-N 0.000 description 1
- DTGHPTNJOJIJHU-UHFFFAOYSA-N 6-methyl-4-phenyl-2-sulfanylidene-3,4-dihydro-1h-pyrimidine-5-carboxamide Chemical compound N1C(=S)NC(C)=C(C(N)=O)C1C1=CC=CC=C1 DTGHPTNJOJIJHU-UHFFFAOYSA-N 0.000 description 1
- SXIMWFPBGWZKAV-UHFFFAOYSA-N 6-phenyl-1h-pyrimidine-2-thione Chemical compound N1C(=S)N=CC=C1C1=CC=CC=C1 SXIMWFPBGWZKAV-UHFFFAOYSA-N 0.000 description 1
- 238000005761 Biginelli synthesis reaction Methods 0.000 description 1
- MIJPXOBUGRETKI-UHFFFAOYSA-N CN1C(NC(C=C1)C1=CC=CC=C1)=S Chemical compound CN1C(NC(C=C1)C1=CC=CC=C1)=S MIJPXOBUGRETKI-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
- 208000019420 lymphoid neoplasm Diseases 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6625183A JPS59190974A (ja) | 1983-04-14 | 1983-04-14 | ５−カルバモイル−６−メチル−４−置換−１，２，３，４−テトラヒドロ−２−チオキソピリミジンの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6625183A JPS59190974A (ja) | 1983-04-14 | 1983-04-14 | ５−カルバモイル−６−メチル−４−置換−１，２，３，４−テトラヒドロ−２−チオキソピリミジンの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59190974A JPS59190974A (ja) | 1984-10-29 |
| JPS627189B2 true JPS627189B2 (zh) | 1987-02-16 |
Family
ID=13310452
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6625183A Granted JPS59190974A (ja) | 1983-04-14 | 1983-04-14 | ５−カルバモイル−６−メチル−４−置換−１，２，３，４−テトラヒドロ−２−チオキソピリミジンの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59190974A (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0574162B2 (zh) * | 1988-07-26 | 1993-10-15 | Matsushita Electric Works Ltd |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5202330A (en) * | 1985-06-03 | 1993-04-13 | E. R. Squibb & Sons, Inc. | 2-thio or oxo-4-aryl or heterocyclo-1,5(2H)-pyrimidinedicarboxylic acid diesters and 3-acyl-5-pyrimidinecarboxylic acids and esters |
| US4675321A (en) * | 1986-02-07 | 1987-06-23 | Merck & Co., Inc. | Substituted pyrimidines useful as calcium channel blockers |
| WO2002066443A2 (en) * | 2001-02-21 | 2002-08-29 | Ono Pharmaceutical Co., Ltd. | 2-thioxo-1,2,3,4-tetrahydropyrimidine derivatives |
-
1983
- 1983-04-14 JP JP6625183A patent/JPS59190974A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0574162B2 (zh) * | 1988-07-26 | 1993-10-15 | Matsushita Electric Works Ltd |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59190974A (ja) | 1984-10-29 |
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