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
Description
本発明は、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（一般式、式中Ｒはアリール
基を意味する）の製造に関するものである。しか
してその意図するところは、制がん作用を有する
化合物として期待される５−カルバモイル−６−
メチル−４−フエニル−１・２・３・４−テトラ
ヒドロ−２−チオキソピリミジン（一般式、式
中Ｒはフエニル基を意味する）およびその同族体
を経済的に有利に製造することにある。
４−フエニル−２−チオキソピリミジン（一般
式、式中Ｒはフエニル基を意味する）は、マウ
スのリンパ性腫瘍に対して顕著な延命効果を有
し、新たな制がん剤として期待されるものである
が、その製造法に関しては、本発明者らはアセト
酢酸アミド、ベンズアルデヒド、およびチオ尿素
を希メタノール（75％）中塩酸の存在で室温下に
放置し69％の収率で得る方法を報告した（加藤
他、薬誌、101、182（1981））。この方法はアセト
酢酸エチル、アルデヒド、および尿素より、５−
エトキシカルボニル−６−メチル−４−置換−
１・２・３・４−テトラヒドロ−２−オキソピリ
ミジン（一般式、式中CONH2の代りに
CO2Et、Ｓの代りにＯ）を製造する所謂ビジネリ
反応（P.Biginelli、Ber.、24、1317（1891））を
応用し、反応条件は全く同一のものであつた。
本発明は、これに対し収率の向上、反応時間の
短縮、さらに反応の一般性と、経済的にも有利な
ものと言える。
すなわち、アセト酢酸アミド１ｇ（10ミリモ
ル）、ベンズアルデヒド1.06ｇ（10ミリモル）、お
よびチオ尿素1.52ｇ（20ミリモル）をイソプロパ
ノール（15ml）に溶かし、濃塩酸（２ml）を加え
て、室温に８時間放置すると、４−フエニル−テ
トラヒドロチオキソピリミジン（一般式、Ｒは
フエニル基）が85％で得られる。反応液を水浴上
加熱還流しても、略々同じ収率で得られる。しか
し、メタノールあるいはエタノールを用いると収
率は低下する。溶媒、反応温度等結果は第一表に
示す通りである。
The present invention provides 5-carbamoyl-6-methyl-4
This invention relates to the production of -substituted-1,2,3,4-tetrahydro-2-thioxopyrimidine (general formula, in which R means an aryl group). However, the intention was to use 5-carbamoyl-6-, which is expected to be a compound with anticancer activity.
To economically advantageously produce methyl-4-phenyl-1,2,3,4-tetrahydro-2-thioxopyrimidine (general formula, in which R means a phenyl group) and its homologues . 4-Phenyl-2-thioxopyrimidine (general formula, where R means a phenyl group) has a remarkable survival effect on lymphoid tumors in mice and is expected to be a new anticancer drug. However, regarding its production method, the present inventors left acetoacetamide, benzaldehyde, and thiourea in the presence of hydrochloric acid in dilute methanol (75%) at room temperature to obtain a yield of 69%. reported the method (Kato et al., Yakuza, 101, 182 (1981)). This method uses ethyl acetoacetate, aldehyde, and urea to produce 5-
ethoxycarbonyl-6-methyl-4-substituted-
1,2,3,4-tetrahydro-2-oxopyrimidine (general formula, where CONH 2 is replaced by
The so-called Biginelli reaction (P. Biginelli, Ber., 24, 1317 (1891)) for producing CO 2 Et (O instead of S) was applied, and the reaction conditions were exactly the same. In contrast, the present invention can be said to be economically advantageous in terms of improved yield, shortened reaction time, and generality of the reaction. That is, 1 g (10 mmol) of acetoacetamide, 1.06 g (10 mmol) of benzaldehyde, and 1.52 g (20 mmol) of thiourea were dissolved in isopropanol (15 ml), concentrated hydrochloric acid (2 ml) was added, and the mixture was left at room temperature for 8 hours. Then, 85% of 4-phenyl-tetrahydrothioxopyrimidine (general formula, R is phenyl group) is obtained. Even if the reaction solution is heated under reflux on a water bath, substantially the same yield can be obtained. However, the yield decreases when methanol or ethanol is used. The results, including the solvent and reaction temperature, are shown in Table 1.
【表】
本発明はさらに他のアルデヒドを用いても同様
に対応するチオキソピリミジン誘導体（一般式
）の製造に対応できる。特に、イソプロパノー
ルを用いると収率が向上する例として、たとえば
ｐ−ニトロベンズアルデヒドを既報の条件すなわ
ち75％メタノール−塩酸に溶かし、室温に放置す
ると、目的とする５−カルバモイル−４−（ｐ−
ニトロフエニル）−６−メチル−１・２・３・４
−テトラヒドロ−２−チオキソピリミジン（一般
式、式中Ｒはｐ−ニトロフエニル基を意味す
る）は33％の収率であるが、イソプロパノール−
濃塩酸の条件では定量的に製造できる。
以下、本発明の方法を実施例により説明する。
実施例 １
５−カルバモイル−６−メチル−４−フエニル
−１・２・３・４−テトラヒドロ−２−チオキ
ソピリミジン（一般式、式中Ｒはフエニル基
を意味する）
(1) 室温に放置する方法
アセト酢酸アミド１ｇ、ベンズアルデヒド
1.06ｇ、およびチオ尿素1.52ｇをイソプロパノ
ール15mlと濃塩酸２mlの混液に溶かし、室温に
放置する。８時間後、析出する結晶を取す
る。母液を濃縮して得られる結晶を合わせ、メ
タノールより再結晶して2.1ｇ（85％）の無色
プリズム、mp236゜（dec.）（文献値mp236゜
（dec。））を得る。
元素分析（C12H13N3OS）
計算値：Ｃ、58.06；Ｈ、5.26；Ｎ、16.88.
実測値：Ｃ、58.37；Ｈ、5.48；Ｎ、16.64.
(2) 加熱還流する方法
上記反応液を水浴上２時間加熱還流する。放
冷後析出する結晶を取、少量のメタノールで
洗浄すると殆んど純品の無色プリズム1.8ｇを
得る。母液を濃縮し、析出する結晶をメタノー
ルより再結晶して0.27ｇの無色プリズムを得
る。総収量2.07ｇ（84％）．mp236゜（dec.）．
実施例 ２
５−カルバモイル−６−メチル−４−（ｐ−ニ
トロフエニル）−１・２・３・４−テトラヒド
ロ−２−チオキソピリミジン（一般式、式中
Ｒはｐ−ニトロフエニル基を意味する）
(1) イソプロパノール−濃塩酸中での反応
アセト酢酸アミド1.0ｇ（10ミリモル）、ｐ−
ニトロベンズアルデヒド1.51ｇ（10ミリモ
ル）、およびチオ尿素1.52ｇ（20ミリモル）を
イソプロパノール15mlと濃塩酸２mlの混液に溶
かし、２時間加熱還流する。放冷後析出する結
晶を取、少量のメタノールで洗浄すると殆ん
ど純品の淡黄色プリズムを得る。収量2.89ｇ
（定量的）．mp258゜（dec.）．
赤外吸収スペクトル（KBr）：3430、3360、
1650cm-1.
元素分析（C12H12N4O3S）
計算値：Ｃ、49.30；Ｈ、4.13；Ｎ、19.16.
実測値：Ｃ、48.97；Ｈ、4.07；Ｎ、18.92.
(2) メタノール−10％塩酸中での反応
アセト酢酸アミド3.03ｇ（30ミリモル）、ｐ
−ニトロベンズアルデヒド4.53ｇ（30ミリモ
ル）、およびチオ尿素4.56ｇ（60ミリモル）を
メタノール45mlと10％塩酸15mlの混液に溶か
し、６日間室温で放置する。析出する結晶を
取し、少量のメタノールで洗浄して殆んど純品
の淡黄色プリズムを2.78ｇ（33％）得る。
mp258゜（dec.）．
同様にして５種類のアルデヒドを用い、新規の
チオキソピリミジン（）を製造した。（第二
表）[Table] The present invention can also be applied to the production of corresponding thioxopyrimidine derivatives (general formula) using other aldehydes. In particular, as an example in which the yield is improved when isopropanol is used, for example, when p-nitrobenzaldehyde is dissolved in 75% methanol-hydrochloric acid and left at room temperature, the desired 5-carbamoyl-4-(p-
Nitrophenyl)-6-methyl-1,2,3,4
The yield of -tetrahydro-2-thioxopyrimidine (general formula, in which R means p-nitrophenyl group) is 33%, but isopropanol-
It can be produced quantitatively under conditions of concentrated hydrochloric acid. The method of the present invention will be explained below using examples. Example 1 5-carbamoyl-6-methyl-4-phenyl-1,2,3,4-tetrahydro-2-thioxopyrimidine (general formula, in which R means a phenyl group) (1) Leave at room temperature Method: 1g of acetoacetamide, benzaldehyde
1.06 g and 1.52 g of thiourea are dissolved in a mixture of 15 ml of isopropanol and 2 ml of concentrated hydrochloric acid and left at room temperature. After 8 hours, collect the precipitated crystals. The crystals obtained by concentrating the mother liquor are combined and recrystallized from methanol to obtain 2.1 g (85%) of colorless prisms, mp236° (dec.) (literature value mp236° (dec.)). Elemental analysis (C 12 H 13 N 3 OS) Calculated value: C, 58.06; H, 5.26; N, 16.88. Actual value: C, 58.37; H, 5.48; N, 16.64. (2) Method of heating to reflux Above reaction Heat the solution to reflux on a water bath for 2 hours. After cooling, the precipitated crystals are collected and washed with a small amount of methanol to obtain 1.8 g of almost pure colorless prisms. The mother liquor is concentrated, and the precipitated crystals are recrystallized from methanol to obtain 0.27 g of colorless prisms. Total yield 2.07g (84%). mp236゜(dec.)． Example 2 5-carbamoyl-6-methyl-4-(p-nitrophenyl)-1,2,3,4-tetrahydro-2-thioxopyrimidine (general formula, in which R means p-nitrophenyl group) (1) Isopropanol - reaction in concentrated hydrochloric acid Acetoacetamide 1.0g (10 mmol), p-
1.51 g (10 mmol) of nitrobenzaldehyde and 1.52 g (20 mmol) of thiourea are dissolved in a mixture of 15 ml of isopropanol and 2 ml of concentrated hydrochloric acid, and heated under reflux for 2 hours. After cooling, the precipitated crystals are collected and washed with a small amount of methanol to obtain almost pure pale yellow prisms. Yield 2.89g
(quantitative). mp258゜(dec.)． Infrared absorption spectrum (KBr): 3430, 3360,
1650cm -1 . Elemental analysis (C 12 H 12 N 4 O 3 S) Calculated value: C, 49.30; H, 4.13; N, 19.16. Actual value: C, 48.97; H, 4.07; N, 18.92. (2) Reaction in methanol-10% hydrochloric acid Acetoacetamide 3.03 g (30 mmol), p
- 4.53 g (30 mmol) of nitrobenzaldehyde and 4.56 g (60 mmol) of thiourea are dissolved in a mixture of 45 ml of methanol and 15 ml of 10% hydrochloric acid and left at room temperature for 6 days. The precipitated crystals were collected and washed with a small amount of methanol to obtain 2.78 g (33%) of almost pure pale yellow prisms.
mp258゜(dec.)． In the same manner, a new thioxopyrimidine () was produced using five types of aldehydes. (Table 2)
【表】【table】
Claims (1)
素をイソプロパノールに溶かし、濃塩酸触媒下、
室温放置または加熱還流を行なうことを特徴とす
る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（下記一般式、式中Ｒはアリール基を
意味する）の製造法。 [Claims] 1. Acetoacetic amide, aldehyde and thiourea are dissolved in isopropanol and catalyzed by concentrated hydrochloric acid.
5-Carbamoyl-6-methyl-4-substituted, characterized by being left at room temperature or heated under reflux.
A method for producing 1,2,3,4-tetrahydro-2-thioxopyrimidine (the following general formula, in which R means an aryl group).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6625183A JPS59190974A (en) | 1983-04-14 | 1983-04-14 | Production of 5-carbamoyl-6-methyl-4-substituted-1,2,3,4- tetrahydro-2-thioxopyrimidine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6625183A JPS59190974A (en) | 1983-04-14 | 1983-04-14 | Production of 5-carbamoyl-6-methyl-4-substituted-1,2,3,4- tetrahydro-2-thioxopyrimidine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59190974A JPS59190974A (en) | 1984-10-29 |
| JPS627189B2 true JPS627189B2 (en) | 1987-02-16 |
Family
ID=13310452
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6625183A Granted JPS59190974A (en) | 1983-04-14 | 1983-04-14 | Production of 5-carbamoyl-6-methyl-4-substituted-1,2,3,4- tetrahydro-2-thioxopyrimidine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59190974A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0574162B2 (en) * | 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/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0574162B2 (en) * | 1988-07-26 | 1993-10-15 | Matsushita Electric Works Ltd |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59190974A (en) | 1984-10-29 |
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