JPH0226631B2 - - Google Patents
Info
- Publication number
- JPH0226631B2 JPH0226631B2 JP55014056A JP1405680A JPH0226631B2 JP H0226631 B2 JPH0226631 B2 JP H0226631B2 JP 55014056 A JP55014056 A JP 55014056A JP 1405680 A JP1405680 A JP 1405680A JP H0226631 B2 JPH0226631 B2 JP H0226631B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- substituent
- carbon atoms
- reaction
- ring
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 7
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 239000003444 phase transfer catalyst Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 15
- 238000000034 method Methods 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000003230 pyrimidines Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- BWHSRLCLYNYUJO-UHFFFAOYSA-N 1,4,5,6,7,8-hexahydro-[1]benzothiolo[2,3-d]pyrimidine Chemical compound N1C=NCC2=C1SC1=C2CCCC1 BWHSRLCLYNYUJO-UHFFFAOYSA-N 0.000 description 1
- CPWQCJFDDILDOU-UHFFFAOYSA-N 2,4-dichloro-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidine Chemical compound C1CCCC2=C1C1=C(Cl)N=C(Cl)N=C1S2 CPWQCJFDDILDOU-UHFFFAOYSA-N 0.000 description 1
- RBBPHGXTPHZELE-UHFFFAOYSA-N 2-chloro-1,4,5,6,7,8-hexahydro-[1]benzothiolo[2,3-d]pyrimidine Chemical compound C1CCCC2=C1C(CN=C(N1)Cl)=C1S2 RBBPHGXTPHZELE-UHFFFAOYSA-N 0.000 description 1
- VCJCJLZVNOZZLS-UHFFFAOYSA-N [1]benzothiolo[2,3-d]pyrimidine Chemical compound C1=NC=C2C3=CC=CC=C3SC2=N1 VCJCJLZVNOZZLS-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- URWCEDLDYLLXCC-UHFFFAOYSA-M decyl(triethyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCC[N+](CC)(CC)CC URWCEDLDYLLXCC-UHFFFAOYSA-M 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
本発明は式 （式中、 The present invention is based on the formula (In the formula,
【式】部分は置換基を有する
こともあるベンゼン環または置換基を有すること
もある縮合様式［２，３−ｄ］のチオフエン環で
あり、置換基としては炭素数１〜４のアルキル基
およびハロゲン原子から選ばれた１または２であ
り、さらにチオフエン環の場合にはチオフエン環
に縮合する５〜７員環を形成するような炭素数３
〜５のアルキレン鎖が置換していてもよく、この
アルキレン鎖は酸素原子または硫黄原子を含んで
もよい。X1はハロゲン原子を意味する。）で示さ
れる化合物に、ベンゼン、クロロホルムおよびメ
チレンクロリドから選ばれた溶媒中で、ヨウ化テ
トラブチルアンモニウム、塩化ベンジルトリエチ
ルアンモニウムおよび臭化テトラブチルホスホニ
ウムから選ばれた相間移動触媒および水酸化アル
カリ水溶液の存在下に式
X2CH2COOR
（式中、Ｒは炭素数１〜４のアルキル基を、
X2はハロゲン原子を意味する。）で示される化合
物を反応させることを特徴とする式
（式中、[Formula] moiety is a benzene ring that may have a substituent or a thiophene ring in the fused mode [2,3-d] that may have a substituent, and substituents include an alkyl group having 1 to 4 carbon atoms and 1 or 2 selected from halogen atoms, and in the case of a thiophene ring, 3 carbon atoms forming a 5- to 7-membered ring fused to the thiophene ring
~5 alkylene chains may be substituted, and the alkylene chains may contain oxygen or sulfur atoms. X 1 means a halogen atom. ), a phase transfer catalyst selected from tetrabutylammonium iodide, benzyltriethylammonium chloride and tetrabutylphosphonium bromide, and an aqueous alkali hydroxide solution in a solvent selected from benzene, chloroform and methylene chloride. In the presence of the formula X 2 CH 2 COOR (wherein R is an alkyl group having 1 to 4 carbon atoms,
X 2 means a halogen atom. ) A formula characterized by reacting a compound represented by (In the formula,
【式】部分、X1およびＲは前
記の定義に等しい。）で示される２−ハロゲノ−
３−アルコキシカルボニルメチル−３，４−ジヒ
ドロ縮合ピリミジン類化合物の新規な製法に関す
るものである。
本発明の化合物は、Ａ部分がチオフエン環を構
成するものは全て新規の化合物である。またベン
ゼン環を構成する化合物も一部の化合物が特開昭
51−70797号公報に殆んど具体的な物性の記載な
く示されているのみである。
本発明の化合物は、式（）で表わされる化合
物の重要な製造中間体である。
例えば、本発明の化合物（）をメタノール等の
不溶性溶媒中、アンモニアと封管中加熱すると式
（）の化合物がえられる。この化合物は極めて
強い血小板凝集抑制作用を示す。
本発明の化合物の製法に関してＡ部分がベンゼ
ン環を構成する化合物は特開昭51−70797号公報
に記載されているが、最終目的物である式（）
の化合物を製造するには不必要に迂遠な工程をと
ることとなるため、中間体として実用価値は小さ
かつた。
そこで本発明者らは、新規な式（）の化合物
をアセトン、メチルエチルケトンもしくはその他
の不活性溶媒中、炭酸アルカリの存在下、式
（）のハロゲノ酢酸エステル類を数時間から20
時間加熱撹拌下に反応させる優れた方法を見い出
した。
（式中The moieties X 1 and R are as defined above. ) 2-halogeno-
The present invention relates to a novel method for producing 3-alkoxycarbonylmethyl-3,4-dihydro-fused pyrimidine compounds. All of the compounds of the present invention in which the A moiety constitutes a thiophene ring are novel compounds. Also, some of the compounds that make up the benzene ring are
No. 51-70797 only discloses it without describing any specific physical properties. The compound of the present invention is an important intermediate in the production of the compound represented by formula (). For example, when the compound () of the present invention is heated with ammonia in a sealed tube in an insoluble solvent such as methanol, a compound of formula () is obtained. This compound exhibits extremely strong platelet aggregation inhibitory effects. Regarding the method for producing the compound of the present invention, a compound in which the A moiety constitutes a benzene ring is described in JP-A-51-70797, but the final target product is the formula ()
Since the production of this compound requires an unnecessarily roundabout process, it has little practical value as an intermediate. Therefore, the present inventors prepared a novel compound of the formula () in acetone, methyl ethyl ketone, or other inert solvent in the presence of an alkali carbonate, and prepared a halogenoacetic acid ester of the formula () for several hours to 20 hours.
We have discovered an excellent method of reacting under heating and stirring for hours. (In the ceremony
【式】部分X1，X2およびＲは
前記と同じものを示す。）
本発明者は、この反応をさらに検討した結果よ
り一層有利な方法を見い出し本発明を完成するこ
とができた。
すなわち、本発明は新規な式（）の化合物、
２−ハロゲノ−３，４−ジヒドロ縮合ピリミジン
類を、相間移動触媒の存在下ハロゲノ酢酸エステ
ル（）と反応させることにより式（）の化合
物を製造する方法である。
相間移動触媒としては、例えば、ヨウ化テトラ
ブチルアンモニウム、臭化ベンジルトリエチルア
ンモニウム、塩化ベンジルトリメチルアンモニウ
ム、塩化ベンジルトリエチルアンモニウム、臭化
デシルトリエチルアンモニウム、臭化テトラブチ
ルホスホニウム等を挙げることができる。これら
の化合物の使用量は触媒量でよいが、目安として
通常、化合物に対しておよそ0.5％から５％モ
ルを使用すればよい。反応はベンゼン、クロロホ
ルム、メチレンクロリド等の水と均一に混和しな
い有機溶媒に式（）の化合物を溶解もしくは懸
濁し、これを式の化合物に対し２倍ないし10倍
モルの水酸化アルカリ水溶液と混和して行なうの
が適当であり、室温で数分ないし数十分で反応は
完結し、80〜95％の好収率で式（）の化合物が
えられる。
この反応の特徴は、反応条件が緩和でかつ後処
理も容易であるため好収率で目的物が単離できる
ことである。すなわち、本発明の方法では室温で
反応が進行するのに対して、先に示した炭酸アル
カリ存在下の反応（以下、先の反応と言う。）は
加熱を要する。また、反応時間も本発明の方法で
は数分から数十分であるのに対して、先の反応で
は20時間を要する。このように本発明の方法を用
いると、緩和な条件で反応を実施することができ
る。また、反応の後処理も本発明の方法では反応
の終了後直ちに水によつて洗浄操作を実施すれば
よいが、先の反応では抽出液の洗浄に先立ち、無
機塩類の濾去、溶媒の留去、抽出といつた操作を
要し、より煩雑である。そしてこれらの特徴か
ら、特に工業的製法として本発明の方法を適用す
ると、製造工程での省力化が可能となる。
次に具体例をもつて本発明を説明するが、これ
らは本発明を限定するものでない。
実施例 １
２−クロル−３，４，５，６，７，８−ヘキサ
ヒドロ〔１〕ベンゾチエノ〔２，３−ｄ〕ピリミ
ジン2.27ｇ、ヨウ化テトラ−ｎ−ブチルアンモニ
ウム（以下TBAIと略する。）185mgを10N水酸化
ナトリウム５mlおよびメチレンクロリド50mlの混
合物に加え、窒素気流下にブロム酢酸エチル1.84
ｇを撹拌下に加える。５分撹拌したのち反応液に
水を加え有機層を分離し、水洗、乾燥後溶媒を留
去するとほゞ定量的に粗製の２−クロル−３−エ
トキシカルボニルメチル３，４，５，６，７，８
−ヘキサヒドロ〔１〕ベンゾチエノ〔２，３−
ｄ〕ピリミジンがえられる。これは粗製のまま次
のアンモニアとの反応に用いることができる。
又、エタノールと共に濾取すると結晶状物質とし
て2.85ｇ（91％）単離することもできる。
融点105〜110℃（分解）。
元素分析 C14H17ClN2O2Sとして
計算値 C53.75，H5.48，N8.95
分析値 C53.48，H5.42，N8.70
ここで出発物質は次のようにして合成した。
２，４−ジクロル−５，６，７，８−テトラヒド
ロ〔１〕ベンゾチエノ〔２，３−ｄ〕ピリミジン
90.7ｇをクロロホルム１に溶解し、エタノール
400mlを加え撹拌下に水素化ホウ素ナトリウム80
ｇを少しづつ加える。添加終了後45〜50℃で15時
間撹拌を続けたのち溶媒を留去する。残査に水を
加えよくかきまぜたのち不溶分を濾取し、よく水
洗すると粗製の２−クロル．３，４，５，６，
７，８−ヘキサヒドロ〔１〕ベンゾチエノ〔２，
３−ｄ〕ピリミジンが殆んど定量的にえられる。
実施例 ２〜11
実施例１と同様にして次に示す前記式の化合
物を合成した。以下表にまとめる。[Formula] The moieties X 1 , X 2 and R are the same as above. ) As a result of further study of this reaction, the present inventors were able to discover a more advantageous method and complete the present invention. That is, the present invention provides novel compounds of formula (),
This is a method for producing a compound of formula () by reacting 2-halogeno-3,4-dihydro condensed pyrimidines with halogenoacetate () in the presence of a phase transfer catalyst. Examples of the phase transfer catalyst include tetrabutylammonium iodide, benzyltriethylammonium bromide, benzyltrimethylammonium chloride, benzyltriethylammonium chloride, decyltriethylammonium bromide, and tetrabutylphosphonium bromide. The amount of these compounds to be used may be a catalytic amount, but as a guide, it is usually sufficient to use approximately 0.5% to 5% mole based on the compound. The reaction is carried out by dissolving or suspending the compound of formula () in an organic solvent that is uniformly immiscible with water, such as benzene, chloroform, methylene chloride, etc., and mixing this with an aqueous alkali hydroxide solution in an amount of 2 to 10 times the molar amount of the compound of formula. The reaction is completed in several minutes to tens of minutes at room temperature, and the compound of formula () is obtained in a good yield of 80 to 95%. The characteristics of this reaction are that the reaction conditions are mild and post-treatment is easy, so the target product can be isolated in good yield. That is, in the method of the present invention, the reaction proceeds at room temperature, whereas the reaction in the presence of an alkali carbonate (hereinafter referred to as the previous reaction) requires heating. Furthermore, the reaction time for the method of the present invention is several minutes to several tens of minutes, whereas the above reaction requires 20 hours. As described above, when the method of the present invention is used, the reaction can be carried out under mild conditions. Furthermore, in the method of the present invention, post-treatment of the reaction may be carried out by washing with water immediately after the completion of the reaction, but in the previous reaction, inorganic salts were removed by filtration and the solvent was distilled off before washing the extract. It requires operations such as removal and extraction, which is more complicated. Due to these characteristics, especially when the method of the present invention is applied as an industrial manufacturing method, it becomes possible to save labor in the manufacturing process. Next, the present invention will be explained using specific examples, but these are not intended to limit the present invention. Example 1 2.27 g of 2-chloro-3,4,5,6,7,8-hexahydro[1]benzothieno[2,3-d]pyrimidine, tetra-n-butylammonium iodide (hereinafter abbreviated as TBAI). ) was added to a mixture of 5 ml of 10N sodium hydroxide and 50 ml of methylene chloride, and 1.84 mg of ethyl bromoacetate was added under a nitrogen stream.
Add g under stirring. After stirring for 5 minutes, water was added to the reaction solution, the organic layer was separated, washed with water, dried, and the solvent was distilled off. 7,8
-hexahydro[1]benzothieno[2,3-
d] Pyrimidine is obtained. This can be used in the next reaction with ammonia in its crude form.
In addition, 2.85 g (91%) of crystalline material can be isolated by filtering it with ethanol. Melting point 105-110℃ (decomposition). Elemental analysis C 14 H 17 ClN 2 O 2 S Calculated value C53.75, H5.48, N8.95 Analytical value C53.48, H5.42, N8.70 Here, the starting material was synthesized as follows. .
2,4-dichloro-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidine
Dissolve 90.7g in chloroform 1, add ethanol
Add 400ml of sodium borohydride while stirring.
Add g little by little. After the addition was completed, stirring was continued for 15 hours at 45-50°C, and then the solvent was distilled off. After adding water to the residue and stirring well, the insoluble matter was filtered and washed thoroughly with water to obtain crude 2-chlor. 3, 4, 5, 6,
7,8-hexahydro[1]benzothieno[2,
3-d]pyrimidine is obtained almost quantitatively. Examples 2 to 11 In the same manner as in Example 1, the following compounds of the above formulas were synthesized. They are summarized in the table below.
【表】【table】
Claims (1)
る縮合様式［２，３−ｄ］のチオフエン環であ
り、置換基としては炭素数１〜４のアルキル基お
よびハロゲン原子から選ばれた１または２であ
り、さらにチオフエン環の場合にはチオフエン環
に縮合する５〜７員環を形成するような炭素数３
〜５のアルキレン鎖が置換していてもよく、この
アルキレン鎖は酸素原子または硫黄原子を含んで
もよい。X1はハロゲン原子を意味する。）で示さ
れる化合物に、ベンゼン、クロロホルムおよびメ
チレンクロリドから選ばれた溶媒中で、ヨウ化テ
トラブチルアンモニウム、塩化ベンジルトリエチ
ルアンモニウムおよび臭化テトラブチルホスホニ
ウムから選ばれた相間移動触媒および水酸化アル
カリ水溶液の存在下に式 X2CH2COOR （式中、Ｒは炭素数１〜４のアルキル基を、
X2はハロゲン原子を意味する。）で示される化合
物を反応させることを特徴とする式 （式中、【式】部分、X1およびＲは前 記の定義に等しい。）」で示される化合物の製法。[Claims] 1 formula (In the formula, the [formula] moiety is a benzene ring that may have a substituent or a thiophene ring in the fused mode [2,3-d] that may have a substituent, and the substituent has 1 to 4 carbon atoms. 1 or 2 selected from alkyl groups and halogen atoms, and in the case of thiophene rings, 3 carbon atoms forming a 5- to 7-membered ring condensed to the thiophene ring.
~5 alkylene chains may be substituted, and the alkylene chains may contain oxygen or sulfur atoms. X 1 means a halogen atom. ), a phase transfer catalyst selected from tetrabutylammonium iodide, benzyltriethylammonium chloride and tetrabutylphosphonium bromide, and an aqueous alkali hydroxide solution in a solvent selected from benzene, chloroform and methylene chloride. In the presence of the formula X 2 CH 2 COOR (wherein R is an alkyl group having 1 to 4 carbon atoms,
X 2 means a halogen atom. ) A formula characterized by reacting a compound represented by (wherein the [formula] moiety, X 1 and R are as defined above).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1405680A JPS56110678A (en) | 1980-02-07 | 1980-02-07 | Preparation of alkoxycarbonylmethyl-substituted condensed pyrimidine compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1405680A JPS56110678A (en) | 1980-02-07 | 1980-02-07 | Preparation of alkoxycarbonylmethyl-substituted condensed pyrimidine compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56110678A JPS56110678A (en) | 1981-09-01 |
| JPH0226631B2 true JPH0226631B2 (en) | 1990-06-12 |
Family
ID=11850425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1405680A Granted JPS56110678A (en) | 1980-02-07 | 1980-02-07 | Preparation of alkoxycarbonylmethyl-substituted condensed pyrimidine compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56110678A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104119344B (en) * | 2014-05-30 | 2017-06-06 | 上海天慈生物谷生物工程有限公司 | The method that one kind prepares the glyoxalidine of 6,7 dichloro- 1,5 simultaneously [2,1 b] quinazoline 2 (3H) ketone |
-
1980
- 1980-02-07 JP JP1405680A patent/JPS56110678A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56110678A (en) | 1981-09-01 |
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