JPS6149309B2 - - Google Patents
Info
- Publication number
- JPS6149309B2 JPS6149309B2 JP52044508A JP4450877A JPS6149309B2 JP S6149309 B2 JPS6149309 B2 JP S6149309B2 JP 52044508 A JP52044508 A JP 52044508A JP 4450877 A JP4450877 A JP 4450877A JP S6149309 B2 JPS6149309 B2 JP S6149309B2
- Authority
- JP
- Japan
- Prior art keywords
- isocyanate
- group
- uracils
- bis
- fluorouracil
- 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
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000005442 diisocyanate group Chemical group 0.000 claims description 3
- -1 diphenylmethylene group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 229910052731 fluorine Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000005079 alkoxycarbonylmethyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000012948 isocyanate Substances 0.000 description 10
- 150000002513 isocyanates Chemical class 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- MPVQFVDWJDULDL-UHFFFAOYSA-N (5-fluoro-2-trimethylsilyloxypyrimidin-4-yl)oxy-trimethylsilane Chemical compound C[Si](C)(C)OC1=NC=C(F)C(O[Si](C)(C)C)=N1 MPVQFVDWJDULDL-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229960002949 fluorouracil Drugs 0.000 description 4
- ANJPRQPHZGHVQB-UHFFFAOYSA-N hexyl isocyanate Chemical compound CCCCCCN=C=O ANJPRQPHZGHVQB-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- AOCCBINRVIKJHY-UHFFFAOYSA-N Carmofur Chemical compound CCCCCCNC(=O)N1C=C(F)C(=O)NC1=O AOCCBINRVIKJHY-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229960003261 carmofur Drugs 0.000 description 3
- 125000004665 trialkylsilyl group Chemical group 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 2
- FSBNTQRWSOTNEW-UHFFFAOYSA-N Pyrimidine, 2,4- bis[(trimethylsilyl)oxy]- Chemical compound C[Si](C)(C)OC1=CC=NC(O[Si](C)(C)C)=N1 FSBNTQRWSOTNEW-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- BCMYXYHEMGPZJN-UHFFFAOYSA-N 1-chloro-2-isocyanatoethane Chemical compound ClCCN=C=O BCMYXYHEMGPZJN-UHFFFAOYSA-N 0.000 description 1
- GFNKTLQTQSALEJ-UHFFFAOYSA-N 1-isocyanato-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(N=C=O)C=C1 GFNKTLQTQSALEJ-UHFFFAOYSA-N 0.000 description 1
- YIDSTEJLDQMWBR-UHFFFAOYSA-N 1-isocyanatododecane Chemical compound CCCCCCCCCCCCN=C=O YIDSTEJLDQMWBR-UHFFFAOYSA-N 0.000 description 1
- RFXBSYPBSRSQDU-UHFFFAOYSA-N 1-isocyanatoheptane Chemical compound CCCCCCCN=C=O RFXBSYPBSRSQDU-UHFFFAOYSA-N 0.000 description 1
- GFLXBRUGMACJLQ-UHFFFAOYSA-N 1-isocyanatohexadecane Chemical compound CCCCCCCCCCCCCCCCN=C=O GFLXBRUGMACJLQ-UHFFFAOYSA-N 0.000 description 1
- QWDQYHPOSSHSAW-UHFFFAOYSA-N 1-isocyanatooctadecane Chemical compound CCCCCCCCCCCCCCCCCCN=C=O QWDQYHPOSSHSAW-UHFFFAOYSA-N 0.000 description 1
- DYQFCTCUULUMTQ-UHFFFAOYSA-N 1-isocyanatooctane Chemical compound CCCCCCCCN=C=O DYQFCTCUULUMTQ-UHFFFAOYSA-N 0.000 description 1
- OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 1
- CSMJMAQKBKGDQX-UHFFFAOYSA-N 1-isocyanatotetradecane Chemical compound CCCCCCCCCCCCCCN=C=O CSMJMAQKBKGDQX-UHFFFAOYSA-N 0.000 description 1
- HACRKYQRZABURO-UHFFFAOYSA-N 2-phenylethyl isocyanate Chemical compound O=C=NCCC1=CC=CC=C1 HACRKYQRZABURO-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- PXXNTSRWKSCFCK-UHFFFAOYSA-N 5-fluoro-2,4-dioxo-n-phenylpyrimidine-1-carboxamide Chemical compound O=C1NC(=O)C(F)=CN1C(=O)NC1=CC=CC=C1 PXXNTSRWKSCFCK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- HXBPYFMVGFDZFT-UHFFFAOYSA-N allyl isocyanate Chemical compound C=CCN=C=O HXBPYFMVGFDZFT-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011737 fluorine Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical compound O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- URIQHRVESCIELP-UHFFFAOYSA-N n-hexyl-2,4-dioxopyrimidine-1-carboxamide Chemical compound CCCCCCNC(=O)N1C=CC(=O)NC1=O URIQHRVESCIELP-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Description
本発明は、１―カルバモイルウラシル類の製造
法に関する。
本発明者は、先にウラシル類とイソシアナート
の反応または、ウラシル類とホスゲンとアミンの
反応によつて１―カルバモイル―ウラシル類を合
成する方法を発明したが、その後、さらに研究を
つづけた結果、１―カルバモイル―ウラシル類の
新規な合成法を見出した。２，４―ビス（トリア
ルキルシリル）―ウラシル類とイソシアナートと
を反応させると次の式にしたがつて１―カルバモ
イルウラシル類が得られる。
（式中R2は低級アルキル基、Ｘは、水素、フ
ツ素、メチル、トリフロロメチル基をあらわし
R1は、例えば、脂肪族、芳香族の置換または無
置換アルキル基、アリール基、アラルキル基など
をあらわす。）イソシアナートはR1に２つ以上の
イソシアナート基がついたジイソシアナート、ポ
リイソシアナートであつてもよい。
イソシアナートの例としては、メチルイソシア
ナート、エチルイソシアナート、プロピルイソシ
アナート、ブチルイソシアナート、ヘキシルイソ
シアナート、ヘプチルイソシアナート、オクチル
イソシアナート、ラウリルイソシアナート、テト
ラデシルイソシアナート、ヘキサデシルイソシア
ナート、オクタデシルイソシアナート、２―クロ
ルエチルイソシアナート、フエニルイソシアナー
ト、ｐ―ニトロフエニルイソシアナート、トリル
イソシアナート、ベンジルイソシアナート、フエ
ネチルイソシアナート、アリルイソシアナート、
２，４―トリレンジイソシアナート、４，4′―ジ
フエニルメタンジイソシアナート、テトラメチレ
ンジイソシアナート等がある。
２，４―ビス（トリアルキルシリル）―ウラシ
ル類の例としては、２，４―ビス（トリメチルシ
リル）―ウラシル、２，４―ビス（トリメチルシ
リル）―５―フルオロウラシル、２，４―ビス
（トリエチルシリル）―５―フルオロウラシル等
がある。
反応を行なうには、２，４―ビス（トリアルキ
ルシリル）―ウラシル類とイソシアナートとを混
合し、混合液にプロトン源となる物質をイソシア
ナートに対し当量程度加えて撹拌をつづければよ
い。プロトン源としては、アルコール類、水、有
機酸、無機酸等があるが、アルコール類例えばエ
タノールが特に好都合である。反応温度は０〜
120℃程度、であるが室温ないし100℃くらいが一
般的である。シリル化ウラシル類とイソシアナー
トのモル比は当量でよいがイソシアナートの方を
少過剰ないし２〜３倍用いた方がシリル化ウラシ
ル類を基準とした収率が上る。反応の進行は薄層
クロマトグラフで追跡することができる。反応後
はクロロホルムを加えて撹拌し、不溶物があれば
過し、クロロホルム層を水洗、乾固して目的物
を得、必要ならばその目的物を再結晶する。
本発明の方法によつて得られる１―カルバモイ
ル―ウラシル類は制ガン剤、抗ビールス剤あるい
は制ガン剤合成の中間体として有用である。
次に実施例により本発明の方法を述べる。
実施例 １
２，４―ビス（トリメチルシリル）―５―フル
オロウラシル1.37g（５ミリモル）とヘキシルイ
ソシアナート1.92g（15ミリモル）をよく混合撹
拌し、この混合液に室温でエタノール0.69g（15
ミリモル）を滴下し、さらに２時間撹拌をつづけ
る。一夜放置後クロロホルム20mlを加えて撹拌し
不溶物を過し、液を水洗後クロロホルムを留
出乾固して、１―ヘキシルカルバモイル―５―フ
ルオロウラシル1.22g（収率95％）を得た。これ
をエタノールより再結晶して、精１―ヘキシルカ
ルバモイル―５―フルオロウラシル（融点 111
℃）を得た。
実施例 ２
２，４―ビス（トリメチルシリル）―５―フル
オロウラシル1.37g（５ミリモル）とヘキシルイ
ソシアナート0.64g（５ミリモル）をよく混合撹
拌し、100℃に加熱し、この混合液にエタノール
0.23gを加えて、さらに２時間100℃で反応を行な
つた。反応後の反応液には、目的化合物80％、５
―フルオロウラシル20％の割合で含まれているこ
とが薄層クロマトグラフイによつて観察された。
反応液にクロロホルム20mlを加えて撹拌し、不溶
物を過して除き、液を水洗したのち、クロロ
ホルムを留去して、１―ヘキシルカルバモイル―
５―フルオロウラシル0.94g（収率73.1％）を得
た。
実施例 ３
２，４―ビス（トリメチルシリル）―５―フル
オロウラシル1.37g（５ミリモル）とヘキシルイ
ソシアナート0.64g（５ミリモル）とをよく混合
撹拌し、この混合液に室温で、アセトン５ml、水
0.09g（５ミリモル）を加えて２時間撹拌をつゞ
けた。
この反応混合物を実施例２と同様に処理して
0.74g（収率57.8％）の１―ヘキシルカルバモイ
ル―５―フルオロウラシルを得た。
実施例 ４
２，４―ビス（トリメチルシリル）―５―フル
オロウラシル1.37gとフエニルイソシアナート
1.19g（10ミリモル）を混合し、これに撹拌しな
がら、メタノール0.32g（10ミリモル）を加えて
50℃で２時間反応させ、実施例１と同様に処理し
て１―フエニルカルバモイル―５―フルオロウラ
シル1.1g（収率90％）を得た。
実施例 ５〜11
２，４―ビス（トリメチルシリル）―５―フル
オロウラシル1.37g（５ミリモル）と表１に示す
イソシアナート10ミリモル（実施例７のジイソシ
アナートは５ミリモル）の混合液に撹拌しながら
エタノール0.46g（10ミリモル）を加えて室温で
５時間撹拌し、実施例１と同様に処理して表１の
１―カルバモイル―５―フルオロウラシル類を得
た。
The present invention relates to a method for producing 1-carbamoyluracils. The present inventor had previously invented a method for synthesizing 1-carbamoyl-uracils by the reaction of uracils and isocyanate or the reaction of uracils, phosgene, and amines, but as a result of further research. discovered a new method for synthesizing 1-carbamoyl-uracils. When 2,4-bis(trialkylsilyl)-uracils are reacted with isocyanate, 1-carbamoyluracils are obtained according to the following formula. (In the formula, R2 represents a lower alkyl group, and X represents hydrogen, fluorine, methyl, or trifluoromethyl group.
R 1 represents, for example, an aliphatic or aromatic substituted or unsubstituted alkyl group, an aryl group, an aralkyl group, or the like. ) The isocyanate may be a diisocyanate or polyisocyanate in which R 1 has two or more isocyanate groups. Examples of isocyanates include methyl isocyanate, ethyl isocyanate, propyl isocyanate, butyl isocyanate, hexyl isocyanate, heptyl isocyanate, octyl isocyanate, lauryl isocyanate, tetradecyl isocyanate, hexadecyl isocyanate, octadecyl Isocyanate, 2-chloroethyl isocyanate, phenyl isocyanate, p-nitrophenyl isocyanate, tolyl isocyanate, benzyl isocyanate, phenethyl isocyanate, allyl isocyanate,
Examples include 2,4-tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, and tetramethylene diisocyanate. Examples of 2,4-bis(trialkylsilyl)-uracils include 2,4-bis(trimethylsilyl)-uracil, 2,4-bis(trimethylsilyl)-5-fluorouracil, and 2,4-bis(triethylsilyl). )-5-fluorouracil, etc. To carry out the reaction, 2,4-bis(trialkylsilyl)-uracils and isocyanate are mixed, a proton source substance is added to the mixture in an equivalent amount to the isocyanate, and stirring is continued. . Proton sources include alcohols, water, organic acids, inorganic acids, etc., with alcohols such as ethanol being particularly advantageous. The reaction temperature is 0~
The temperature is around 120℃, but room temperature or around 100℃ is common. The molar ratio of the silylated uracils and the isocyanate may be equivalent, but the yield based on the silylated uracils will be higher if the isocyanate is used in slight excess to 2 to 3 times the amount. The progress of the reaction can be followed by thin layer chromatography. After the reaction, chloroform is added and stirred, and any insoluble matter is filtered off. The chloroform layer is washed with water and dried to obtain the desired product. If necessary, the desired product is recrystallized. The 1-carbamoyl-uracils obtained by the method of the present invention are useful as anticancer agents, antiviral agents, or intermediates for the synthesis of anticancer agents. Next, the method of the present invention will be described by way of examples. Example 1 1.37 g (5 mmol) of 2,4-bis(trimethylsilyl)-5-fluorouracil and 1.92 g (15 mmol) of hexyl isocyanate were thoroughly mixed and stirred, and 0.69 g (15 mmol) of ethanol was added to this mixture at room temperature.
mmol) was added dropwise, and stirring was continued for an additional 2 hours. After standing overnight, 20 ml of chloroform was added and stirred to remove insoluble materials. After washing the liquid with water, the chloroform was distilled off to dryness to obtain 1.22 g of 1-hexylcarbamoyl-5-fluorouracil (yield 95%). This was recrystallized from ethanol and purified 1-hexylcarbamoyl-5-fluorouracil (melting point 111
°C) was obtained. Example 2 1.37 g (5 mmol) of 2,4-bis(trimethylsilyl)-5-fluorouracil and 0.64 g (5 mmol) of hexyl isocyanate were thoroughly mixed and stirred, heated to 100°C, and ethanol was added to the mixture.
0.23g was added and the reaction was further carried out at 100°C for 2 hours. After the reaction, the reaction solution contained 80% of the target compound and 5% of the target compound.
- It was observed by thin layer chromatography that it contained 20% fluorouracil.
20 ml of chloroform was added to the reaction solution and stirred, insoluble materials were removed by filtration, the solution was washed with water, the chloroform was distilled off, and 1-hexylcarbamoyl-
0.94 g (yield 73.1%) of 5-fluorouracil was obtained. Example 3 1.37 g (5 mmol) of 2,4-bis(trimethylsilyl)-5-fluorouracil and 0.64 g (5 mmol) of hexyl isocyanate were thoroughly mixed and stirred, and 5 ml of acetone and water were added to this mixture at room temperature.
0.09 g (5 mmol) was added and stirring continued for 2 hours. The reaction mixture was treated as in Example 2.
0.74 g (yield 57.8%) of 1-hexylcarbamoyl-5-fluorouracil was obtained. Example 4 1.37 g of 2,4-bis(trimethylsilyl)-5-fluorouracil and phenyl isocyanate
Mix 1.19g (10mmol) and add 0.32g (10mmol) of methanol while stirring.
The mixture was reacted at 50° C. for 2 hours, and treated in the same manner as in Example 1 to obtain 1.1 g (yield: 90%) of 1-phenylcarbamoyl-5-fluorouracil. Examples 5 to 11 A mixture of 1.37 g (5 mmol) of 2,4-bis(trimethylsilyl)-5-fluorouracil and 10 mmol of the isocyanate shown in Table 1 (5 mmol of the diisocyanate in Example 7) was stirred. At the same time, 0.46 g (10 mmol) of ethanol was added, and the mixture was stirred at room temperature for 5 hours, and treated in the same manner as in Example 1 to obtain the 1-carbamoyl-5-fluorouracils shown in Table 1.
【表】
実施例 12
実施例１の２，４―ビス（トリメチルシリル）
―５―フルオロウラシルの代わりに２，４―ビス
（トリメチルシリル）ウラシル1.28g（５ミリモ
ル）を用いた以外は実施例１と同様にして反応を
行ない、１―ヘキシルカルバモイル―ウラシル
1.07g（収率90％、融点183℃）を得た。[Table] Example 12 2,4-bis(trimethylsilyl) of Example 1
The reaction was carried out in the same manner as in Example 1, except that 1.28 g (5 mmol) of 2,4-bis(trimethylsilyl)uracil was used instead of -5-fluorouracil, and 1-hexylcarbamoyl-uracil was used.
1.07g (yield 90%, melting point 183°C) was obtained.
Claims (1)
素原子を表わす。〕で表される２，４―ビス（ト
リアルキルシリル）ウラシル類と一般式(2) R1―NCO (2) 〔式中R1は炭素数１ないし18のアルキル基、
アルケニル基、置換又は無置換フエニル基、置換
又は無置換のアラルキル基およびアルコキシカル
ボニルメチル基を表す。〕で表わされるイソシア
ナート類あるいは、一般式(3) OCN―Ａ―NCO (3) 〔式中Ａは炭素数１ないし６のアルキレン基、
置換または無置換フエニレン基およびジフエニル
メチレン基を表す。〕で表されるジイソシアナー
ト類をプロトン源の存在下に反応させることを特
徴とする１―カルバモイル―ウラシル類の製造
法。[Claims] 1 General formula (1) [In the formula, R represents a lower alkyl group, and X represents hydrogen or a fluorine atom. ] 2,4-bis(trialkylsilyl)uracils represented by the general formula (2) R 1 -NCO (2) [wherein R 1 is an alkyl group having 1 to 18 carbon atoms,
It represents an alkenyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted aralkyl group, and an alkoxycarbonylmethyl group. ] or general formula (3) OCN-A-NCO (3) [wherein A is an alkylene group having 1 to 6 carbon atoms,
Represents a substituted or unsubstituted phenylene group and diphenylmethylene group. ] A method for producing 1-carbamoyl-uracils, which comprises reacting diisocyanates represented by the following in the presence of a proton source.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4450877A JPS53130679A (en) | 1977-04-20 | 1977-04-20 | Preparation of 1-carbamoyl-uracil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4450877A JPS53130679A (en) | 1977-04-20 | 1977-04-20 | Preparation of 1-carbamoyl-uracil |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS53130679A JPS53130679A (en) | 1978-11-14 |
| JPS6149309B2 true JPS6149309B2 (en) | 1986-10-29 |
Family
ID=12693486
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4450877A Granted JPS53130679A (en) | 1977-04-20 | 1977-04-20 | Preparation of 1-carbamoyl-uracil |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS53130679A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0442644B2 (en) * | 1987-02-05 | 1992-07-14 | Fujikura Densen Kk |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5663966A (en) * | 1979-10-29 | 1981-05-30 | Tokyo Kinzoku Kogyo Kk | Pyrimidine derivative and its preparation |
| JPS5785374A (en) * | 1980-11-18 | 1982-05-28 | Mitsui Toatsu Chem Inc | 5-fluorouracil derivative and its preparation |
| US4497815A (en) * | 1983-01-05 | 1985-02-05 | Shoichiro Ozaki | 1-(N-Substituted carbamoyl)-5-fluorouracil derivatives and the carcinostatic agents containing same as active ingredients |
| BR112014029365A2 (en) * | 2012-05-22 | 2017-06-27 | Hoffmann La Roche | selective undifferentiated cell inhibitors |
| ITMI20120921A1 (en) * | 2012-05-28 | 2013-11-29 | Fond Istituto Italiano Di Tec Nologia 45 | INHIBITORS OF CERAMIDASIS ACID AND THEY USE AS MEDICATIONS |
-
1977
- 1977-04-20 JP JP4450877A patent/JPS53130679A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0442644B2 (en) * | 1987-02-05 | 1992-07-14 | Fujikura Densen Kk |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS53130679A (en) | 1978-11-14 |
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