JPH0378857B2 - - Google Patents
Info
- Publication number
- JPH0378857B2 JPH0378857B2 JP15209584A JP15209584A JPH0378857B2 JP H0378857 B2 JPH0378857 B2 JP H0378857B2 JP 15209584 A JP15209584 A JP 15209584A JP 15209584 A JP15209584 A JP 15209584A JP H0378857 B2 JPH0378857 B2 JP H0378857B2
- Authority
- JP
- Japan
- Prior art keywords
- mol
- aminocrotonamide
- methylpyrimidine
- formate
- hydroxy
- 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
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 17
- UAUSQEVPWPGBHG-IHWYPQMZSA-N (z)-3-aminobut-2-enamide Chemical compound C\C(N)=C\C(N)=O UAUSQEVPWPGBHG-IHWYPQMZSA-N 0.000 claims description 14
- 235000019253 formic acid Nutrition 0.000 claims description 7
- -1 formic acid ester Chemical class 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 4
- AHHHDTLXONDKQF-UHFFFAOYSA-N 6-methyl-1h-pyrimidin-2-one Chemical compound CC1=CC=NC(O)=N1 AHHHDTLXONDKQF-UHFFFAOYSA-N 0.000 claims 1
- LHRIUKSRPHFASO-UHFFFAOYSA-N 6-methyl-1h-pyrimidin-4-one Chemical compound CC1=CC(=O)N=CN1 LHRIUKSRPHFASO-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- AVMSWPWPYJVYKY-UHFFFAOYSA-N 2-Methylpropyl formate Chemical compound CC(C)COC=O AVMSWPWPYJVYKY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VUXKVKAHWOVIDN-UHFFFAOYSA-N Cyclohexyl formate Chemical compound O=COC1CCCCC1 VUXKVKAHWOVIDN-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- ZMFWTUBNIJBJDB-UHFFFAOYSA-N 6-hydroxy-2-methylquinoline-4-carboxylic acid Chemical compound C1=C(O)C=CC2=NC(C)=CC(C(O)=O)=C21 ZMFWTUBNIJBJDB-UHFFFAOYSA-N 0.000 description 1
- BVPHXTUEZOQIBS-UHFFFAOYSA-N 6-methyl-1h-pyrimidine-2-thione Chemical compound CC1=CC=NC(S)=N1 BVPHXTUEZOQIBS-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- OUGPMNMLWKSBRI-UHFFFAOYSA-N Hexyl formate Chemical compound CCCCCCOC=O OUGPMNMLWKSBRI-UHFFFAOYSA-N 0.000 description 1
- RMOUBSOVHSONPZ-UHFFFAOYSA-N Isopropyl formate Chemical compound CC(C)OC=O RMOUBSOVHSONPZ-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- QLBKLJFKEUBMGH-UHFFFAOYSA-N cyclopentyl formate Chemical compound O=COC1CCCC1 QLBKLJFKEUBMGH-UHFFFAOYSA-N 0.000 description 1
- 230000003009 desulfurizing effect Effects 0.000 description 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- KDIDLLIMHZHOHO-UHFFFAOYSA-N prop-2-ynyl formate Chemical compound O=COCC#C KDIDLLIMHZHOHO-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- MFBOGIVSZKQAPD-UHFFFAOYSA-M sodium butyrate Chemical compound [Na+].CCCC([O-])=O MFBOGIVSZKQAPD-UHFFFAOYSA-M 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- WWNBZGLDODTKEM-UHFFFAOYSA-N sulfanylidenenickel Chemical compound [Ni]=S WWNBZGLDODTKEM-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は４−ヒドロキシ−６−メチルピリミジ
ンの製造方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for producing 4-hydroxy-6-methylpyrimidine.
４−ヒドロキシ−６−メチルピリミジンは医
薬、農薬その他の中間体として有用である。 4-Hydroxy-6-methylpyrimidine is useful as an intermediate for pharmaceuticals, agricultural chemicals, and others.
従来、４−ヒドロキシ−６−メチルピリミジン
は、下記式で示されるように、アセト酢酸エステ
ルとチオ尿素とを反応させて、４−ヒドロキシ−
２−メルカプト−６−メチルピリミジンを合成
し、これをラネーニツケルにより脱硫して製造す
る方法が知られている（Org.Syn。，Vol.35，
80）。
Conventionally, 4-hydroxy-6-methylpyrimidine was produced by reacting acetoacetate and thiourea as shown in the following formula.
A method of synthesizing 2-mercapto-6-methylpyrimidine and desulfurizing it with Raney nickel is known (Org. Syn., Vol. 35,
80).
しかしながら、この方法では硫化ニツケルが多
量に生成し、工業的には満足すべきものではなか
つた。 However, this method produced a large amount of nickel sulfide and was not industrially satisfactory.
また、３−アミノクロトンアミドとエステル類
とから塩基の存在下に２−置換−４−ヒドロキシ
−６−メチルピリミジンを得る方法は公知であ
り、薬誌，90509（1970）に記載があるが、３−ア
ミノクロトンアミドとギ酸エステルとから４−ヒ
ドロキシ−６−メチルピリミジンを得ることがで
きなかつたと記載されている。 Furthermore, a method for obtaining 2-substituted-4-hydroxy-6-methylpyrimidine from 3-aminocrotonamide and esters in the presence of a base is known and is described in Yakuza, 90 509 (1970). It is stated that 4-hydroxy-6-methylpyrimidine could not be obtained from 3-aminocrotonamide and formic acid ester.
本発明は、３−アミノクロトンアミドとギ酸エ
ステル類とから４−ヒドロキシ−６−メチルピリ
ミジンを高収率で製造する方法を提供する。
The present invention provides a method for producing 4-hydroxy-6-methylpyrimidine from 3-aminocrotonamide and formic acid esters in high yield.
本発明によれば、３−アミノクロトンアミドを
塩基存在下にギ酸エステル類と反応させる４−ヒ
ドロキシ−６−メチルピリミジンの製造方法が提
供される。 According to the present invention, a method for producing 4-hydroxy-6-methylpyrimidine is provided in which 3-aminocrotonamide is reacted with a formic acid ester in the presence of a base.
本発明による方法では重金属化合物の副生がな
く、安価な３−アミノクロトンアミドを原料とし
て、工業的に有利に４−ヒドロキシ−６−メチル
ピリミジンを製造することができる。
The method according to the present invention does not produce by-products of heavy metal compounds, and 4-hydroxy-6-methylpyrimidine can be industrially advantageously produced using inexpensive 3-aminocrotonamide as a raw material.
以下に本発明を詳しく説明する。 The present invention will be explained in detail below.
本発明に使用される３−アミノクロトンアミド
は、例えばTetrahedron，232965（1967）に記載
されている方法により、ジケテンとアンモニアか
ら容易に合成できる。 The 3-aminocrotonamide used in the present invention can be easily synthesized from diketene and ammonia, for example, by the method described in Tetrahedron, 232965 (1967).
本発明に使用される塩基の具体例としてはナト
リウムメチラート、ナトリウムエチラート、ナト
リウムブチラート、ナトリウムシクロヘキシラー
トなどのナトリウムアルコラート、カリウム−ｔ
−ブチラートなどのカリウムアルコラートが挙げ
られる。これらの塩基は、アルコール類に、ナト
リウム又はカリウムの金属、水酸化物又は水素化
物などを溶解させることにより得られ、そのまま
反応に使用することができる。塩基の使用量は出
発原料の３−アミノクロトンアミド１モルに対し
て0.5〜５モル、特に１〜３モルが好ましい。 Specific examples of bases used in the present invention include sodium alcoholates such as sodium methylate, sodium ethylate, sodium butyrate, and sodium cyclohexylate;
- Potassium alcoholates such as butyrate. These bases can be obtained by dissolving sodium or potassium metals, hydroxides, hydrides, etc. in alcohols, and can be used as they are in the reaction. The amount of the base used is preferably 0.5 to 5 mol, particularly 1 to 3 mol, per 1 mol of 3-aminocrotonamide as a starting material.
本発明において使用されるギ酸エステル類とし
てはギ酸メチル、ギ酸エチル、ギ酸イソプロピ
ル、ギ酸イソブチル、ギ酸ｎ−ヘキシル、ギ酸ｎ
−オクチルなどのギ酸アルキルエステル類、ギ酸
シクロペンチル、ギ酸シクロヘキシルなどのギ酸
シクロアルキルエステル類、ギ酸アリルなどのギ
酸アルケニルエステル類、ギ酸プロパルギルなど
のギ酸アルキニル類が挙げられる。ギ酸エステル
の使用量は３−アミノクロトンアミド１モルに対
して１モル以上が好ましく、溶媒としても使用で
きる。 Examples of formic acid esters used in the present invention include methyl formate, ethyl formate, isopropyl formate, isobutyl formate, n-hexyl formate, and n-formate.
Examples include formic acid alkyl esters such as -octyl, formic acid cycloalkyl esters such as cyclopentyl formate and cyclohexyl formate, formic acid alkenyl esters such as allyl formate, and alkynyl formates such as propargyl formate. The amount of formic acid ester used is preferably 1 mol or more per 1 mol of 3-aminocrotonamide, and it can also be used as a solvent.
反応温度は40〜180℃、特に60〜160℃が好まし
い。 The reaction temperature is preferably 40 to 180°C, particularly 60 to 160°C.
本発明に使用される溶媒としては、ギ酸エステ
ル類以外に、メタノール、エタノール、イソプロ
ピルアルコール、ｎ−ブチルアルコール、シクロ
ヘキシルアルコール、アリルアルコール、メトキ
シエタノール、エトキシエタノールなどのアルコ
ール類、エチレングリコールジメチルエーテル、
ジ−ｎ−ブチルエーテル、テトラヒドロフラン、
ジオキサンなどのエーテル類、ジメチルスルホキ
シド、Ｎ，Ｎ−ジメチルホルムアミドが挙げられ
る。これらの溶媒は単独かまたは二種以上を混合
して反応に用いることができる。 In addition to formic acid esters, solvents used in the present invention include alcohols such as methanol, ethanol, isopropyl alcohol, n-butyl alcohol, cyclohexyl alcohol, allyl alcohol, methoxyethanol, and ethoxyethanol, ethylene glycol dimethyl ether,
di-n-butyl ether, tetrahydrofuran,
Examples include ethers such as dioxane, dimethyl sulfoxide, and N,N-dimethylformamide. These solvents can be used alone or in combination of two or more in the reaction.
次に本発明の実施例を示す。なお各例における
目的物の収率は、３−アミノクロトンアミド基準
である。
Next, examples of the present invention will be shown. Note that the yield of the target product in each example is based on 3-aminocrotonamide.
実施例 １
100mlの三角フラスコに３−アミノクロトンア
ミド3.0ｇ（0.03モル）とギ酸エチル3.5ｇ（0.05
モル）を仕込み、金属ナトリウム1.4ｇ（0.06モ
ル）を無水エタノール20mlに溶解した液を加え、
５時間加熱還流した。反応終了後、酢酸で中和
し、析出物をろ過し、エタノールで洗浄した後、
ろ液を濃縮し、カラムクロマトグラフにより精製
し、1.82ｇの白色結晶（m.p.146〜148℃）の４−
ヒドロキシ−６−メチルピリミジンを得た（収率
55％）。Example 1 3.0 g (0.03 mol) of 3-aminocrotonamide and 3.5 g (0.05 mol) of ethyl formate were placed in a 100 ml Erlenmeyer flask.
mol), add a solution of 1.4 g (0.06 mol) of metallic sodium dissolved in 20 ml of absolute ethanol,
The mixture was heated under reflux for 5 hours. After the reaction was completed, the precipitate was neutralized with acetic acid, filtered, and washed with ethanol.
The filtrate was concentrated and purified by column chromatography to obtain 1.82 g of white crystals (mp 146-148°C) of 4-
Hydroxy-6-methylpyrimidine was obtained (yield
55%).
実施例 ２
ギ酸エチル5.2ｇ（0.07モル）を仕込んだ以外
は実施例１と同様に反応し、同様に処理した結
果、2.74ｇの４−ヒドロキシ−６−メチルピリミ
ジン（m.p.147〜149℃）を得た。収率は83％であ
つた。Example 2 The reaction was carried out in the same manner as in Example 1 except that 5.2 g (0.07 mol) of ethyl formate was charged, and as a result of the same treatment, 2.74 g of 4-hydroxy-6-methylpyrimidine (mp 147-149°C) was obtained. Ta. The yield was 83%.
実施例 ３
100mlの三角フラスコに５mlの無水エタノール
と20mlの無水ジオキサンを仕込み、NaH1.4ｇ
（0.06モル）を加え、１時間撹拌した後、３−ア
ミノクロトンアミド3.0ｇ（0.03モル）と、ギ酸
エチル5.2ｇ（0.07モル）を加え、５時間加熱還
流した。反応終了後、実施例１と同様に操作を行
い、2.38ｇの４−ヒドロキシ−６−メチルピリミ
ジンを得た（収率72％）。Example 3 5 ml of absolute ethanol and 20 ml of anhydrous dioxane were placed in a 100 ml Erlenmeyer flask, and 1.4 g of NaH was added.
(0.06 mol) and stirred for 1 hour, 3.0 g (0.03 mol) of 3-aminocrotonamide and 5.2 g (0.07 mol) of ethyl formate were added, and the mixture was heated under reflux for 5 hours. After the reaction was completed, the same procedure as in Example 1 was carried out to obtain 2.38 g of 4-hydroxy-6-methylpyrimidine (yield: 72%).
実施例 ４
100mlの三角フラスコに25mlのイソブチルアル
コールを仕込み、NaH0.7ｇ（0.03モル）を加え
溶解させた後、３−アミノクロトンアミド3.0ｇ
（0.03モル）とギ酸イソブチル5.2ｇ（0.05モル）
を加え、９時間加熱還流した。反応終了後、実施
例１と同様に操作し、1.5ｇの目的物を得た（収
率45％）。Example 4 Pour 25 ml of isobutyl alcohol into a 100 ml Erlenmeyer flask, add and dissolve 0.7 g (0.03 mol) of NaH, and then add 3.0 g of 3-aminocrotonamide.
(0.03 mol) and isobutyl formate 5.2 g (0.05 mol)
was added and heated under reflux for 9 hours. After the reaction was completed, the same procedure as in Example 1 was carried out to obtain 1.5 g of the desired product (yield: 45%).
実施例 ５
100mlの三角フラスコに25mlのシクロヘキサノ
ールを仕込み、NaH1.4ｇ（0.06モル）を加え、
溶解させた後、３−アミノクロトンアミド3.0ｇ
（0.03モル）とギ酸シクロヘキシル11.5ｇ（0.09モ
ル）を加え、140℃で３時間加熱した。反応終了
後、実施例１と同様に操作した結果、61％の収率
で目的物を得た。Example 5 Pour 25 ml of cyclohexanol into a 100 ml Erlenmeyer flask, add 1.4 g (0.06 mol) of NaH,
After dissolving, 3.0 g of 3-aminocrotonamide
(0.03 mol) and 11.5 g (0.09 mol) of cyclohexyl formate were added and heated at 140°C for 3 hours. After the reaction was completed, the same procedure as in Example 1 was carried out to obtain the desired product with a yield of 61%.
実施例 ６
100mlの三角フラスコに6.0ｇ（0.06モル）の３
−アミノクロトンアミドと25mlのギ酸エチルを仕
込み、NaOCH33.2ｇ（0.06モル）を溶解したメ
タノール溶液20mlを加え、10時間加熱還流した。
反応終了後、実施例１と同様に操作を行い、77％
の収率で目的物を得た。Example 6 6.0g (0.06mol) of 3 in a 100ml Erlenmeyer flask
-Aminocrotonamide and 25 ml of ethyl formate were charged, and 20 ml of a methanol solution in which 3.2 g (0.06 mol) of NaOCH 3 was dissolved was added, followed by heating under reflux for 10 hours.
After the reaction was completed, the same operation as in Example 1 was carried out, and 77%
The target product was obtained in a yield of .
Claims (1)
酸エステル類と反応させることを特徴とする４−
ヒドロキシ−６−メチルピリミジンの製造方法。1 4- characterized by reacting 3-aminocrotonamide with formic acid ester in the presence of a base
Method for producing hydroxy-6-methylpyrimidine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15209584A JPS6130575A (en) | 1984-07-24 | 1984-07-24 | Preparation of 4-hydroxy-6-methylpyrimidine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15209584A JPS6130575A (en) | 1984-07-24 | 1984-07-24 | Preparation of 4-hydroxy-6-methylpyrimidine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6130575A JPS6130575A (en) | 1986-02-12 |
| JPH0378857B2 true JPH0378857B2 (en) | 1991-12-17 |
Family
ID=15532935
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15209584A Granted JPS6130575A (en) | 1984-07-24 | 1984-07-24 | Preparation of 4-hydroxy-6-methylpyrimidine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6130575A (en) |
-
1984
- 1984-07-24 JP JP15209584A patent/JPS6130575A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6130575A (en) | 1986-02-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |