Day: September 7, 2021

Electric Literature of 720-01-4 ,Some common heterocyclic compound, 720-01-4, molecular formula is C8H6ClF3N2O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

A suspension of ethyl 4-chloro-2-(trifluoromethyl)pyrimidine-5-carboxylate (1.00 g), O-benzylhydroxylamine hydrochloride (0.69 g), and potassium carbonate (1.19 g) in THF (15 mL) was stirred at room temperature for 3 hours. To the reaction mixture, ethyl acetate and water were added. An organic layer was separated, washed with a saturated aqueous solution of sodium chloride and then dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 98-65% hexane/ethyl acetate] to obtain a white solid of ethyl 4-((benzyloxy)amino)-2-(trifluoromethyl)pyrimidine-5-carboxylate (1.27 g). 1H-NMR (CDCl3) delta value: 1.39 (t, J=7.2 Hz, 3H), 4.38 (q, J=7.2 Hz, 2H), 5.06 (s, 2H), 7.35-7.44 (m, 3H), 7.47-7.54 (m, 2H), 8.96 (s, 1H), 10.47 (s, 1H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 720-01-4, Ethyl 4-chloro-2-trifluoromethylpyrimidine-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Toyama Chemical Co., Ltd.; KAWAI, Hyouei; MURATA, Daigo; SUZUMURA, Yuko; EP2810944; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 51940-64-8 ,Some common heterocyclic compound, 51940-64-8, molecular formula is C7H6Cl2N2O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Potassium carbonate (78 g, 565 mmol) was added to ethyl 2,4-dichloropyrimidine-5- carboxylate (50.0 g, 226 mmol) and cis-4-aminocyclohexanol hydrochloride (34.3 g, 226 mmol) in acetonitrile (700 mL) at rt under air. The reaction mixture was stirred at rt for 16 h. The mixture was filtered through a Celite pad. The filtrate was concentrated under reduced pressure. The precipitate was collected by filtration, washed with MeCN (100 mL) and dried under vacuum to afford the title compound (41.0 g, 61%) as a white solid; 1H NMR (400 MHz, DMSO) 1.32 (3H, t), 1.42 – 1.58 (2H, m), 1.60 – 1.75 (6H, m), 3.66 (1H, d), 4.06 (1H, dd), 4.33 (2H, q), 4.57 (1H, d), 8.46 (1H, d), 8.63 (1H, s); m/z MH+ 300.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 51940-64-8, Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; CANCER RESEARCH TECHNOLOGY LIMITED; FINLAY, Maurice, Raymond, Verschoyle; GOLDBERG, Frederick, Woolf; TING, Attilla, Kuan, Tsuei; (103 pag.)WO2018/114999; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 3993-78-0, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 3993-78-0, name is 2-Amino-4-chloropyrimidine. A new synthetic method of this compound is introduced below.

A mixture of 4-fluoropiperidine hydrochloride (4.9 g, 35.1 mmol), 4-chloropyrimidin-2-amine (5.00 g, 38.6 mmol) and potassium carbonate (14.6 g, 105 mmol) in N-methyl-2-pyrrolidinone (15.0 mL) was stirred under argon for 2 h at 120 C. The reaction mixture was cooled to room temperature, was poured into NaOH (1 M) and ice and was extracted twice with ethyl acetate. The organic layers were washed with brine, combined, dried over Na2SC>4, filtered and the volatiles were evaporated to yield 8.33 g of a light yellow waxy solid. The solid was triturated with tert. butyl methylether (-10 mL) and stirred for 30 min. Then the suspension was filtrated and dried under high vacuum to yield 6.38 g (83 %, contains residual N-methyl-2-pyrrolidinone) of a light yellow solid. MS: m/z = 197.5 (M+H)+ ; The product was obtained starting from 1 -(2-fluoroethyl)piperazine hydrochloride (705 mg, 3.55 mmol), 4-chloropyrimidin-2-amine (506 mg, 3.91 mmol) and potassium carbonate (1.47 g, 10.7 mmol) in N-methyl-2-pyrrolidinone (1.5 mL) according to the method described in example 2, step 1 after overnight heating as light brown solid (642 mg, 79 ). MS: m/z = 226.6 (M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3993-78-0, 2-Amino-4-chloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GOBBI, Luca; KNUST, Henner; KOERNER, Matthias; MURI, Dieter; WO2014/187762; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 271-70-5, Adding some certain compound to certain chemical reactions, such as: 271-70-5, name is 7H-Pyrrolo[2,3-d]pyrimidine,molecular formula is C6H5N3, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 271-70-5.

To 7H-pyrrolo[2,3-]pyrimidine (6, 1.00 g, 8.39 mmol), (2,4-difluoro-3-formyl-phenyl)-carbamic acid benzyl ester (22, 2.93 g, 10.1 mmol), and potassium hydroxide (1.53 g, 27.3 mmol), 10.0 mL of methanol was added. The solution was allowed to stir at room temperature for 32 hours, then poured into 25 mL of water and 25 mL of saturated ammonium chloride and extracted 2×50 mL with ethyl acetate. The combined organic layer was concentrated under vacuum. The crude material was purified by silica gel column chromatography eluting with a gradient of 0-80% ethyl acetate in hexane (with 4% acetic acid) over 15 minutes. Appropriate fractions were combined and concentrated under vacuum to provide 1.066 g of a mixture of compounds 23 and 24, which was used in the next step without further purification. MS(ESI) [M+H+]+=335.4.

According to the analysis of related databases, 271-70-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Plexxikon, Inc.; US2009/286783; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 113583-35-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 113583-35-0, name is 2-Methanesulfonyl-4,6-dimethoxypyrimidine, molecular formula is C7H10N2O4S, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

0.04 mol of 2,6-dihydroxybenzoic acid was weighed separately,0.05 mol of 2-methanesulfonyl-4,6-dimethoxypyrimidine,0.004 mol of tetrabutylammonium bromide,0.08 mol of potassium carbonate was placed in a reaction vessel,Add 300mL toluene heated reflux reaction 8 ~ 1 Oh,The reaction is cooled and filtered,The filter cake was washed with toluene,dry,The resulting solid was mixed with 500 mL of water,Stir,Dropping 30% HC1 to the system PH = 3 ~ 4,filter,dry,Was gray and solidbodyBispyribac15.7g,Purity 97%Yield 85%.

According to the analysis of related databases, 113583-35-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zibo Xinnong Jinongyao Chemical Co.,Ltd; ZHENG, YOUKUI; SONG, JUN; WANG, XIAOWEI; (5 pag.)CN106083738; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 7752-78-5, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 7752-78-5, name is 5-Bromo-2-methylpyrimidine. A new synthetic method of this compound is introduced below.

A solution of 5-bromo-2-iodopyrimidine (5.00 g, 17.6 mmol) in 25 mL of THF was cooled to 00C under nitrogen. Dimethyl zinc (2.0 M in toluene, 13.2 mL, 26.3 mmol) and palladium tetrakis (5 molpercent) were added. After 5 hours, aqueous ammonium chloride (5 mL) was added, and the reaction mixture was warmed to room temperature. The mixture was diluted with ethyl acetate (30 mL) and washed with aqueous sodium bicarbonate (2 x 30 mL) and brine (30 mL). The combined organic extracts were dried, filtered and concentrated in vacuo to provide 5- bromo-2-methylpyridine that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 173.1 for M+H* (79Br). To a solution of the above compound (3.40 g, 19.6 mmol) in 100 mL of CCl4 (25 mL) was added N-bromosuccinimide (6.98 g, 39.2 mmol) and 2,2′-azobisisobutyronitrile (2.30 g, 14.0 mmol). The reaction was heated to 1000C for 24 hours, then cooled to room temperature and washed with aqueous sodium bicarbonate and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated. The crude material was subjected to chromatography on silica gel eluting with 0-5percent EtOAc in hexanes to yield the title compound as a pale yellow needles which gave a proton nuMR spectrum consistent with theory and a mass ion (ES+) of 252.8 for M+H+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7752-78-5, 5-Bromo-2-methylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; WO2009/134668; (2009); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 16019-31-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 16019-31-1, name is 5-Allyl-4,6-dichloropyrimidine, molecular formula is C7H6Cl2N2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Step 3 – Synthesis of Compound ID; Compound 1C (9.73 g, 51.47 mmol) was dissolved in a mixture of acetone: water (1:1,290 mL) and to the resulting solution was added potassium osmate dihydrate (0.64 g, 1.75 mmol). The resulting solution was allowed so stir for 5 minutes, then solid sodium periodate (44 g, 205.37 mmol) was added in 4 portions over a 1 hour period. The temperature of the reaction didn’t exceed 400C during this addition. The resulting suspension was allowed to stir for 1 hour as the reaction cooled to room temperature on its own. The reaction mixture was then filtered and the filtrate was concentrated in vacuo to remove acetone. The resulting aqueous solution was extracted 2 times with dichloromethane and the combined organic layers were washed with 10% sodium thiosulfate solution, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to provide compound ID (8.16 g, 83.01%).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 16019-31-1, 5-Allyl-4,6-dichloropyrimidine.

Reference:
Patent; SCHERING CORPORATION; NEELAMKAVIL, Santhosh, Francis; BOYLE, Craig D.; NEUSTADT, Bernard, R.; CHACKALAMANNIL, Samuel; GREENLEE, William, J.; WO2010/9208; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1004-38-2, Adding some certain compound to certain chemical reactions, such as: 1004-38-2, name is 2,4,6-Triaminopyrimidine,molecular formula is C4H7N5, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1004-38-2.

General procedure: A mixture of 2,4,6-triaminopyrimidine 1 (1.0 mmol), 3-(2-cyanoacetyl)indole 2 (1.0 mmol), appropriate aromatic aldehyde (1.0 mmol) and indium chloride (0.05 mmol) in ethanol (5.0 mL) were subjected to microwave irradiation for 10 min at 120 C. After completion of the reaction (monitored by TLC using a dichloromethane-ethanol (9:1) mixture as the mobile phase), the reaction mixture was cooled and filtered. The solid product obtained was initially washed with ethanol, and finally recrystallized from ethanol.

According to the analysis of related databases, 1004-38-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Enriz, Ricardo D.; Tosso, Rodrigo D.; Andujar, Sebastian A.; Cabedo, Nuria; Cortes, Diego; Nogueras, Manuel; Cobo, Justo; Vargas, Didier F.; Trilleras, Jorge; Tetrahedron; vol. 74; 49; (2018); p. 7047 – 7057;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1780-33-2, 4,6-Dichloro-2,5-dimethylpyrimidine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Recommanded Product: 4,6-Dichloro-2,5-dimethylpyrimidine, blongs to pyrimidines compound. Recommanded Product: 4,6-Dichloro-2,5-dimethylpyrimidine

General procedure: Two solutions, one with the aryl halide (0.56 mmol, 1.0equivalent) in THF?H2O (2.5 mL, 3:2 v/v) and one with phenol (0.84mmol, 1.5 equivalent) and NaOH (0.84 mmol, 1.5 equivalent) in THF?H2O(2.5 mL, 3:2 v/v) were prepared and then introduced into Asia microfluidicreactor by Pump A & B.. The mixture was pumped through a preheated 1 mL glassmicrofluidic reactor at a predetermined flow rate to achieve the desiredresidence time. The crude product was collected in a flask and extracted withethyl acetate. The organic phase was combined, dried MgSO4 andconcentrated under reduced pressure. The isolated crude product was purifiedusing a prepacked silica cartridge on a Teledyne CombiFlash Rf 200instrument. Fractions corresponding to the product peak were combined andconcentrated using rotavap. For the synthesis of compound 3e and 3f correspondingsodium alkoxides were used as input for the second pump. 4-Chloro-6-(4-methoxy-2-methylphenoxy)-2,5-dimethylpyrimidine(3a). White solid (135 mg, 87percent). 1H NMR (CDCl3) d 2.08(s, 3H), 2.36 (s, 3H), 2.41 (s, 3H), 3.79 (s, 3H), 6.72?6.79 (m, 2H) and 6.94(d, J = 8.4 Hz, 1H); 13CNMR (CDCl3) d 11.6, 16.7, 25.5, 55.6, 111.9, 113.0, 116.2,122.6, 131.3, 144.9, 157.1, 160.1, 165.2 and 168.1; mass spectrum (APCI), m/zcalcd for C14H16ClN2O2 (M+H)+279.0895, found 279.0888.

The synthetic route of 1780-33-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Alam, Mohammad Parvez; Jagodzinska, Barbara; Campagna, Jesus; Spilman, Patricia; John, Varghese; Tetrahedron Letters; vol. 57; 19; (2016); p. 2059 – 2062;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 5305-59-9, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.5305-59-9, name is 6-Chloropyrimidin-4-amine, molecular formula is C4H4ClN3, molecular weight is 129.55, as common compound, the synthetic route is as follows.

Synthesis of tert-butyl N-tert-butoxycarbonyl-N-(6-chloropyrimidin-4-yl)carbamate (2) To a stirred solution of 6-chloropyrimidin-4-amine (1, 1 g, 7.75 mmol) in tetrahydrofuran (20 mL), 4-(dimethylamino)pyridine (0.047 g, 0.387 mmol) and di-tert-butyl dicarbonate (3.55 g, 16.27 mmol) were added dropwise. The reaction mixture was stirred at room temperature for 16 h. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with water and extracted with ethyl acetate. Combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford tert-butyl N-tert-butoxycarbonyl-N-(6-chloropyrimidin-4-yl)carbamate (2) which was used for the next step without further purification. Yield: 1.3 g, 51%; MS (ESI) m/z 330 [M+1]+.

Statistics shows that 5305-59-9 is playing an increasingly important role. we look forward to future research findings about 6-Chloropyrimidin-4-amine.

Reference:
Patent; eFFECTOR Therapeutics, Inc.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; Shaghafi, Mike; Murphy, Douglas; Tran, Chinh; (131 pag.)US10112955; (2018); B2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia