JPS63270681A - Production of 6-n-benzylamino-9-benzylpurines - Google Patents
Production of 6-n-benzylamino-9-benzylpurinesInfo
- Publication number
- JPS63270681A JPS63270681A JP10580387A JP10580387A JPS63270681A JP S63270681 A JPS63270681 A JP S63270681A JP 10580387 A JP10580387 A JP 10580387A JP 10580387 A JP10580387 A JP 10580387A JP S63270681 A JPS63270681 A JP S63270681A
- Authority
- JP
- Japan
- Prior art keywords
- aminopurine
- benzylamines
- hydrochloride
- formula
- general formula
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 18
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229930024421 Adenine Natural products 0.000 claims abstract description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000003939 benzylamines Chemical class 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- XKXHCNPAFAXVRZ-UHFFFAOYSA-N benzylazanium;chloride Chemical compound [Cl-].[NH3+]CC1=CC=CC=C1 XKXHCNPAFAXVRZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000010438 heat treatment Methods 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 2
- 125000000542 sulfonic acid group Chemical group 0.000 claims 2
- MDOUSORGCMUMBO-UHFFFAOYSA-N 9-benzylpurine Chemical class C1=NC2=CN=CN=C2N1CC1=CC=CC=C1 MDOUSORGCMUMBO-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 13
- 239000002994 raw material Substances 0.000 abstract description 10
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 150000005018 aminopurines Chemical class 0.000 abstract 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 230000001766 physiological effect Effects 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003212 purines Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JILFAECPQYQHLB-UHFFFAOYSA-N 2-benzyl-7h-purine Chemical compound N=1C=C2NC=NC2=NC=1CC1=CC=CC=C1 JILFAECPQYQHLB-UHFFFAOYSA-N 0.000 description 1
- RXIMIBAZIQKSFF-UHFFFAOYSA-N 2-n-benzylpyridine-2,5-diamine Chemical compound N1=CC(N)=CC=C1NCC1=CC=CC=C1 RXIMIBAZIQKSFF-UHFFFAOYSA-N 0.000 description 1
- KWXVDUACPKJCCN-UHFFFAOYSA-N 4-[(3,4-diethoxyphenyl)methylamino]benzenecarboximidamide Chemical compound C1=C(OCC)C(OCC)=CC=C1CNC1=CC=C(C(N)=N)C=C1 KWXVDUACPKJCCN-UHFFFAOYSA-N 0.000 description 1
- 229960000643 adenine Drugs 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
６−Ｎ−ベンジルアミノ−９−ベンジルプリン類は生物
に対して生理活性作用があり、農業、バイオテクノロジ
ーの分野で利用できる。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) 6-N-benzylamino-9-benzylpurines have physiologically active effects on living organisms and can be used in the fields of agriculture and biotechnology.
（従来の技術）
ドイツ特許第２１，２２３号（１９５８）には、６−Ｎ
−ベンジルアミノ−９−ベンジルプリンに防カビ作用が
あり、４，６−ビヌー（ベンジルアミノ）−５−アミノ
ピリミジンの閉環反応による製法の記載がある。(Prior Art) German Patent No. 21,223 (1958) describes 6-N
-Benzylamino-9-benzylpurine has an antifungal effect, and there is a description of a manufacturing method using a ring-closing reaction of 4,6-binu(benzylamino)-5-aminopyrimidine.
（当該発明が解決しようとする問題点）４，６−ビス−
（ベンジルアミノ）−５−アミノピリジンを原料とする
公知の方法は原料の合成に４段階以上の反応を必要とし
、はん雑で工業的には採用されない。(Problem to be solved by the invention) 4,6-bis-
The known method using (benzylamino)-5-aminopyridine as a raw material requires four or more reaction steps to synthesize the raw material, is complicated and cannot be used industrially.
特公昭４Ｂ−７９５５に記載されている６−アミノプリ
ンと１級アミン類及び塩酸等との反応は原料の入手が容
易で有利であるが、反応の主生成物が６−Ｎ−ペンシル
アミノプリンであり、目的物の収率は低く工業的に採用
できない。The reaction of 6-aminopurine with primary amines, hydrochloric acid, etc. described in Japanese Patent Publication No. 4B-7955 is advantageous because raw materials are easily available, but the main product of the reaction is 6-N-pencylaminopurine. However, the yield of the target product is low and cannot be used industrially.
このことは以下に述べる発明者らの実験で明らかである
。This is clear from the inventors' experiments described below.
実験例（１）
窒素気流中で６−アミノプリ７２．５ ？ （９，８ｍ
ｍｏｌ ）ベンジルアミン５ ｌｉｅ （４５，９皿ｏ
１ ）ベンジルアミン塩酸塩２．５１を反応容器に入
れ、１５０°Ｃで１５時間反応する。反応終了後冷却し
、エチルエーテルを加え、生成する沈澱を戸別、水洗す
る。残渣をクロロホルムで抽出し、抽出液を濃縮し、得
られる結晶をエタノールで再結晶すれば融点１７７〜１
７８°Ｃの６−Ｎ−ベンジルアミノ−９−ベンジルプリ
ンが得られた。。Experimental example (1) 6-aminopuri 72.5 ? in a nitrogen stream (9.8m
mol) benzylamine 5 lie (45,9 dishes o
1) Put 2.51 g of benzylamine hydrochloride into a reaction vessel and react at 150°C for 15 hours. After the reaction is completed, the mixture is cooled, ethyl ether is added, and the precipitate formed is washed with water one by one. The residue is extracted with chloroform, the extract is concentrated, and the resulting crystals are recrystallized with ethanol to give a melting point of 177-1.
6-N-benzylamino-9-benzylpurine at 78°C was obtained. .
クロロホルム抽出残渣をエタノール抽出し、抽出液を濃
縮、冷却すればｍｐ２３２°Ｃの６−Ｎ−ベンジルアミ
ノプリンが得られた。The chloroform extraction residue was extracted with ethanol, and the extract was concentrated and cooled to obtain 6-N-benzylaminopurine with a mp of 232°C.
使用原料比、反応条件を変え、実：険例１と同様に処理
した結果を下記の表（１）にまとめる。The results were summarized in Table (1) below, which was treated in the same manner as Example 1 by changing the raw material ratio and reaction conditions.
（問題点を解決するための手段）
発明者は公知の方法での問題点を解決し、工業的に有利
な方法を発明した。すなわち、窒素気流中で６−アミノ
プリンｌ ｍｏｌに対して２ｍｏ１以上のベンジルアミ
ン類と１ｍｏ１以上のその塩酸塩を加え、攪拌等により
均一な混合系とし、１８０°Ｃ以上に加熱し、６−Ｎ−
ベンジルアミノ−９−ペンシルプリンを高収率で得る方
法を発明した。(Means for solving the problems) The inventor solved the problems with the known methods and invented an industrially advantageous method. That is, 2 mol or more of benzylamines and 1 mol or more of their hydrochloride are added to 1 mol of 6-aminopurine in a nitrogen stream, a homogeneous mixture is obtained by stirring, etc., and the mixture is heated to 180°C or higher to form a 6-aminopurine. N-
A method for obtaining benzylamino-9-pencylpurine in high yield has been invented.
以下にこの発明の詳細を述べる。The details of this invention will be described below.
ベンジルアミン類はベンジルアミノ基に対シてオルソま
だはパラ位に水素原子、塩素等のハロゲン原子、水酸基
、メチル、メトオキシ基等の置換基を有する化合物であ
り、その使用量は６−アミノプリンに対して２倍ｍｏ１
以上の量であシ、攪拌等で均一な混合糸が得られる量で
良いが工業的には３〜５倍ｍｏｌがよい。Benzylamines are compounds having substituents such as hydrogen atoms, halogen atoms such as chlorine, hydroxyl groups, methyl, methoxy groups, etc. in the ortho or para position to the benzylamino group, and the amount used is 6-aminopurine. 2 times mo1 for
The above amount may be enough to obtain a uniform mixed yarn by stirring, stirring, etc., but from an industrial perspective, 3 to 5 times the mol is preferable.
ベンジルアミン類塩酸塩はこの反応では不可欠であり、
使用しない場合は、原料を回収するのみである。Benzylamine hydrochloride is essential in this reaction;
If it is not used, the raw material is simply recovered.
その使用量は６−アミノプリンと同ｍｏ１以上テあれば
よいが経済的−を考慮し、６−アミノプリンと同ｍｏ＋
が望ましい。The amount used should be at least the same mo1 as 6-aminopurine, but considering economical reasons,
is desirable.
まだ、ベンジルアミン類塩酸塩の代用として、６−アミ
ノプリンと同ｍｏ＋の濃塩酸及びペンシルアミン類を使
用してもよく、その添加順序は問わない。However, as a substitute for benzylamine hydrochloride, concentrated hydrochloric acid and pencilamines having the same mo+ as 6-aminopurine may be used, and the order of addition is not limited.
６−アミノプリン、ベンジルアミン類トベンジルアミン
塩酸塩もしくは塩酸を攪拌後で均一な混合系にし、１８
０°Ｃ以上、安全性を考慮して１８０°Ｃで２４〜４８
時間加熱することで収率７３％以上で６−Ｎ−ベンジ７
ｙアミノ−９−ペンシルプリン類を得ることが出来る。6-Aminopurine, benzylamines tobenzylamine hydrochloride or hydrochloric acid are stirred and mixed into a homogeneous system, and 18
0°C or higher, 24-48 at 180°C for safety reasons
6-N-bendi 7 with a yield of 73% or more by heating for hours.
yamino-9-pencyl purines can be obtained.
カくシて、容易に入手できる６−アミノプリン（別称ア
デニン）を原料とし、高収率で、単一反応で６−Ｎ−ベ
ンジルアミノ−９−ペンシルプリン類を得る目的を達成
できる。The purpose of obtaining 6-N-benzylamino-9-pencyl purines in a single reaction in high yield can be achieved using easily available 6-aminopurine (also known as adenine) as a raw material.
実施例１
市販６−アミノプリン２５Ｐ（０，１８５ｍ０＋）、ベ
ンジルアミン６０ｓｔ（０，５５ｍ０Ｉ） ペンシル
アミン塩酸塩２５ ？ （０，１７５ｍｏ＋）を反応容
器に加え、攪拌しながら窒素気流中で１８０°Ｃで２４
時間反応する。Example 1 Commercially available 6-aminopurine 25P (0,185m0+), benzylamine 60st (0,55m0I) Pencylamine hydrochloride 25? (0,175 mo+) was added to the reaction vessel and heated at 180 °C for 24 hours in a nitrogen stream with stirring.
Time reacts.
反応終了後、冷却しエチルエーテルを加え、生成する沈
澱物を戸別し、水洗する。残渣をクロロホルムで抽出し
、抽出液を濃縮し、得られる粗結晶をエタノールから再
結晶すれば、白色結晶の６−Ｎ−ペンシルアミノ−９−
ベンジルプリン４４．３２（収率７３％）が得られた。After the reaction is completed, it is cooled and ethyl ether is added, and the precipitate formed is separated and washed with water. The residue is extracted with chloroform, the extract is concentrated, and the resulting crude crystals are recrystallized from ethanol to obtain white crystals of 6-N-pencylamino-9-
44.32 of benzylpurine (yield 73%) was obtained.
融点 １７７〜１７８°Ｃ
ＩＲ（ＫＢｒ）３２７０．１６２３．１５８３．１３４
５．１３３０．１３００．
１２５０．７３５．７０２．６４８
ＮＭＲｃ（Ｄｃ６ａ）
８．５８（Ｓ、ＩＨ）７．７０（Ｓ、ＩＨ）７．４０（
Ｓ、１０Ｈ）６．６８（ｂｔ、ＩＨ。Melting point 177-178°C IR (KBr) 3270.1623.1583.134
5.1330.1300. 1250.735.702.648 NMRc (Dc6a) 8.58 (S, IH) 7.70 (S, IH) 7.40 (
S, 10H) 6.68 (bt, IH.
Ｊ ＝ ｂＨｚ） ５．４３ （Ｓ 、 ２Ｈ） ４．
９３（ｄ、２ＨＪ ＝ ｂ）（ｚ ）
元素分析
Ｃ１０Ｎ１７ Ｎ５として
計算値（％）、Ｃ７２，３５，Ｈ５，４３，Ｎ２２．２
１実測値（％）、Ｃ７２，３６，Ｈ５，３４，Ｎ２２．
３０実施例２
窒素気流中で市販６−アミノプリン２．５？、ペンシル
アミン１２１ｔｔを反応容器に入れ攪拌しながら、濃塩
酸１．５ ｄを滴下してから１８０°Ｃで４８時間反応
する。実施例（υと同様に処理し、６−Ｎ−ベンジルア
ミノ−９−ベンジルプリン４．３１（収率７３％）を得
る。J = bHz) 5.43 (S, 2H) 4.
93 (d, 2HJ = b) (z) Elemental analysis C10N17 Calculated value (%) as N5, C72,35,H5,43,N22.2
1 actual value (%), C72, 36, H5, 34, N22.
30 Example 2 Commercially available 6-aminopurine 2.5? , 121 tt of pencil amine was placed in a reaction vessel, 1.5 d of concentrated hydrochloric acid was added dropwise with stirring, and the mixture was reacted at 180°C for 48 hours. Treat in the same manner as in Example (υ) to obtain 4.31 (yield 73%) of 6-N-benzylamino-9-benzylpurine.
Claims (2)
表わすベンジルアミン類とベンジルアミン塩酸塩を１８
０℃以上に加熱することを特徴とする一般式（２）で表
わす６−Ｎ−ベンジルアミノ−９−ベンジルプリン類の
製造方法。(1) In a nitrogen stream, 6-aminopurine, benzylamines represented by general formula (1), and benzylamine hydrochloride were mixed into 18
A method for producing 6-N-benzylamino-9-benzylpurines represented by general formula (2), which comprises heating to 0°C or higher.
表わすベンジルアミン類と塩酸を１８０℃以上に加熱す
ることを特徴とする一般式（２）で表わす６−Ｎ−ベン
ジルアミノ−９−ベンジルプリン類の製造方法。 一般式（１） ▲数式、化学式、表等があります▼ 式中Ｘは水素原子
、塩素等 のハロゲン原子、水酸基、メ チル基、メトオキシ基、スル ホン酸基を表わす。 一般式（２） ▲数式、化学式、表等があります▼ 式中Ｘは水素原子
、塩素等の ハロゲン原子、水酸基、メチル基、 メトオキシ基、スルホン酸基、を 表わす。(2) 6-N-benzylaminopurine represented by the general formula (2), which is characterized by heating 6-aminopurine, a benzylamine represented by the general formula (1), and hydrochloric acid to 180°C or higher in a nitrogen stream. Method for producing 9-benzylpurines. General formula (1) ▲There are numerical formulas, chemical formulas, tables, etc.▼ In the formula, X represents a hydrogen atom, a halogen atom such as chlorine, a hydroxyl group, a methyl group, a methoxy group, or a sulfonic acid group. General formula (2) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ In the formula, X represents a hydrogen atom, a halogen atom such as chlorine, a hydroxyl group, a methyl group, a methoxy group, or a sulfonic acid group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62105803A JP2567394B2 (en) | 1987-04-29 | 1987-04-29 | Process for producing 6-N-benzylamino-9-benzylpurines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62105803A JP2567394B2 (en) | 1987-04-29 | 1987-04-29 | Process for producing 6-N-benzylamino-9-benzylpurines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63270681A true JPS63270681A (en) | 1988-11-08 |
| JP2567394B2 JP2567394B2 (en) | 1996-12-25 |
Family
ID=14417273
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62105803A Expired - Lifetime JP2567394B2 (en) | 1987-04-29 | 1987-04-29 | Process for producing 6-N-benzylamino-9-benzylpurines |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2567394B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5391739A (en) * | 1989-03-29 | 1995-02-21 | Merrell Dow Pharmaceuticals Inc. | Selective adenosine receptor agents |
-
1987
- 1987-04-29 JP JP62105803A patent/JP2567394B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5391739A (en) * | 1989-03-29 | 1995-02-21 | Merrell Dow Pharmaceuticals Inc. | Selective adenosine receptor agents |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2567394B2 (en) | 1996-12-25 |
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