Pyrimidines

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. 959070-42-9, name is Ethyl 4,6-dichloro-2-(methylthio)pyrimidine-5-carboxylate. A new synthetic method of this compound is introduced below., category: pyrimidines

The mixture of ethyl 4,6-dichloro-2-(methylthio)pyrimidine-5-carboxylate (7.9 g, 29.88 mmol) and ethyl 4-((4-methoxybenzyl)amino)butanoate (5 g, 19.92 mmol) in DMF (500 mL) and DIPEA (4.6 g, 35.85 mmol) was heated at 80 C. for 2 h. The reaction mixture was then cooled to room temperature and crushed ice was added. The reaction mixture was extracted with EtOAc (3¡Á100 mL), and the combined EtOAc layer was dried over sodium sulphate, filtered and evaporated under reduced pressure to give a residue which was purified by column chromatography (silica gel, gradient 0-5% EtOAc in hexanes) to afford ethyl 4-chloro-6-((4-ethoxy-4-oxobutyl)(4-methoxybenzyl)amino)-2-(methylthio)pyrimidine-5-carboxylate (5.5 g, 40%). 1H NMR (400 MHz, CDCl3): delta 7.12 (d, J=8.4 Hz, 2H), 6.85 (d, J=8.4 Hz, 2H), 4.66 (s, 2H), 4.16 (q, J=6.8 Hz, 2H), 4.10 (q, J=7.2 Hz, 2H), 3.79 (s, 3H), 3.42 (t, J=7.6 Hz, 2H), 2.45 (s, 3H), 2.24 (t, J=6.8 Hz, 2H), 1.94 (quintet, J=7.2 Hz, 2H), 1.24 (t, J=7.2 Hz, 3H), 1.22 (t, J=7.2 Hz, 3H). LCMS [M+H]: 482

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 959070-42-9, Ethyl 4,6-dichloro-2-(methylthio)pyrimidine-5-carboxylate.

Reference:
Patent; ArQule, Inc.; US2010/249110; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 51957-32-5, name is 4-Chloro-5-methylpyrimidine, the common compound, a new synthetic route is introduced below. Computed Properties of C5H5ClN2

A 2 M aqueous Na2CO3 solution (1 .51 ml_) is added to a mixture of 4-chloro-5- methyl-pyrimidine (186 mg) and 4-boronobenzoic acid (200 mg) in N,N- dimethylformamide (5 ml_). The mixture is sparged with argon for 3 min and [1 ,1 ‘- bis(diphenylphosphino)-ferrocene]dichloropalladium dichloromethane complex (100mg) is added. The resulting mixture is stirred at 80C overnight. After cooling to room temperature, water is added and the mixture is treated with charcoal. The solids are filtered off and rinsed with water. The filtrate is extracted with ethyl acetate. The aqueous phase is acidified with 4 M hydrochloric acid and extracted with ethyl acetate. The combined extracts are dried over MgSO4 and concentrated in vacuo. The residue is triturated with diisopropyl ether and the precipitate is filtered off and dried to give the title compound. LC (method 4): tR = 0.77 min; Mass spectrum (EST): m/z = 215 [M+H]+.

The synthetic route of 51957-32-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; NEUROCRINE BIOSCIENCES, INC.; NOSSE, Bernd; BLUM, Andreas; HECKEL, Armin; HIMMELSBACH, Frank; ASHWEEK, Neil J.; HARRIOTT, Nicole; WO2014/37327; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 14394-70-8, Adding some certain compound to certain chemical reactions, such as: 14394-70-8, name is 2-Chloro-5-methylpyrimidin-4-amine,molecular formula is C5H6ClN3, 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 14394-70-8.

[0290] A mixture of l-brorno-3,5-dimethylbenzene (104 muL, 0.77 mmol), 2-chloro-5- methyl-pyrimidin-4-ylamine (104 mg, 0.72 mmol), Pd(OAC)2 (15 mg, 0.07 mmol), Xantphos (83 mg, 0.14 mmol) and potassium terf-butoxide (159 mg, 1.42 mmol) in dioxane (8 mL) was microwaved at 160 C for 20 min. The reaction mixture was cooled to room temperature and filtered rinsing with DCM and methanol. The filtrate was concentrated and purified using gradient flash chromatography (0-100% ethyl acetate in hexanes) to afford the title compound as a yellow oil (89 mg, 50%). MS (ES+): m/z 248 (M+H)+.

According to the analysis of related databases, 14394-70-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TARGEGEN, INC.; WO2007/53452; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 42754-96-1, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 42754-96-1, name is 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Add 4,6-dichloro-1H-pyrazolo [3,4-d] pyrimidine 1a (120 mg, 0.63 mmol),4-methoxybenzylamine 1b (87.1 mg, 0.63 mmol) and triethylamine (64.13 mg, 0.63 mmol) were dissolved in 2 mL of a tetrahydrofuran solution and stirred at room temperature for 1 hour.The reaction was stopped and distilled under reduced pressure. The residue was purified by silica gel column chromatography using eluent system A,The title product 1c (140 mg) was obtained in a yield of 76.1%.

According to the analysis of related databases, 42754-96-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jiangsu Hengrui Pharmaceutical Co., Ltd.; Shanghai Hengrui Pharmaceutical Co., Ltd.; Cao Xiaoli; Du Zhenxing; Wang Likun; (40 pag.)CN110526917; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 99844-02-7, name is 4-(4-Methoxyphenyl)pyrimidin-2-amine, the common compound, a new synthetic route is introduced below. name: 4-(4-Methoxyphenyl)pyrimidin-2-amine

Sodium t-butoxide is added to a stirred suspension of anilino-pyrimidines, substituted sulfones, tris(dibenzylideneacetone)dipalladium(0), and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl in dioxane. The mixture is heated at 80 C. for 72 hours. The reaction is cooled to room temperature, and the mixture is filtered and washed with THF and MeOH. The solvent is removed by evaporation, and the residue is purified by pre-plate with EtOAc/MeOH (10:1.5).

The synthetic route of 99844-02-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth; US2006/79543; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 153435-63-3 , The common heterocyclic compound, 153435-63-3, name is 2-(Tributylstannyl)pyrimidine, molecular formula is C16H30N2Sn, 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 round bottom flask containing 4-(5-bromo-thiazol-2-yl)-piperazine-1- carboxylic acid tert-butyl ester (100 mg, 0.29 mmol), 2-tributylstannanyl-pyrimidine (130 mg, 0.36 mmol), cesium fluoride (85 mg, 0.56 mmol) and palladium di-tert- butylphosphine was degassed three times with Ar. Dioxane was added and the formed reaction mixture was stirred at 90 C overnight under Ar. Then the reaction mixture was filter through celite and the solvent was removed under vacuum and crude product was used directly in the next step.

The synthetic route of 153435-63-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2008/156739; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 579476-26-9, 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. 579476-26-9, name is 3-Pyrimidin-2-yl-benzoic acid, molecular formula is C11H8N2O2, 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.

[00219] To a solution of N-(4-chlorophenyl)-5,5-difluoropiperidine-3-carboxamide (50 mg, 0.18 mmol) in THF (2 ml) was added 3-(pyrimidin-2-yl)benzoic acid (44 mg, 0.22 mmol) followed by N-(3-dimethylaminopropyl)-N?-ethylcarbodiimide hydrochloride (52 mg, 0.27 mmol), N,N-diisopropylethylamine (0.095 ml, 0.55 mmol), and 4- (dimethylamino)pyridine (4.4 mg, 0.036 mmol). The reaction stirred overnight at room temperature. The reaction mixture was poured into ethyl acetate and washed with saturated aqueous sodium bicarbonate solution and brine. The organic layer was dried over magnesium sulfate, filtered, and concetrated. The crude residue was purified by column chromatography eluting with 40-60% ethyl acetate in hexanes to give the title compound (75mg, 90%). ?H NMR (400 MHz, DMSO-d6, 80 C) oe 10.04, 8.90, 8.49, 8.43, 7.63, 7.56, 7.44, 7.32, 4.33, 4.20, 3.57, 3.25, 3.00, 2.96, 2.46, 2.30.

According to the analysis of related databases, 579476-26-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; BOARD OF TRUSTEES OF MICHIGAN STATE UNIVERSITY; LARSEN, Scott, D.; NEUBIG, Richard; HAAK, Andrew; HUTCHINGS, Kim; RAJESWARAN, Walajapet; (156 pag.)WO2016/73847; (2016); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 13479-88-4, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 13479-88-4 as follows.

Step 1 5-Chloro-N-(5,6-dimethoxypyridin-2-yl)thiazolo[5,4-d]pyrimidin-7-amine Procedure: A solution of 5,7-dichlorothiazolo[5,4-d]pyrimidine (300 mg, 1.45 mmol), 5,6-dimethoxypyridin-2-amine (269 mg, 1.74 mmol) and DIEA (281 mg, 2.17 mmol) in 5 mL of DMSO was stirred at room temperature for 24 hours. Then the mixture was poured into 30 mL of water, and the formed solid was filtered and washed with water. The obtained crude product was purified by silica gel chromatography (silica gel 200-300 mesh, eluting with ethyl acetate) to give 5-chloro-N-(5,6-dimethoxypyridin-2-yl)thiazolo[5,4-d]pyrimidin-7-amine (344 mg, 73%) as an off-white solid. LC-MS: 324.1 [M+H]+, tR=1.69 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13479-88-4, its application will become more common.

Reference:
Patent; Hermann, Johannes Cornelius; Lowrie, JR., Lee Edwin; Lucas, Matthew C.; Luk, Kin-Chun Thomas; Padilla, Fernando; Wanner, Jutta; Xie, Wenwei; Zhang, Xiaohu; US2012/252777; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 25193-95-7, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 25193-95-7, name is 5-(Hydroxymethyl)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Example 27 Synthesis of 3,5-dimethyl-4-hydroxy-6-(5-(5-pyrimidinylmethoxy)benzofuran-2-yl)-2H-pyran-2-one A solution of tributylphosphine in 2 N THF (0.94 ml) and a solution of TMAD (323 mg) in CH2Cl2 (3 ml) were added dropwise to a solution of 4-acetyloxy-3,5-dimethyl-6-(5-hydroxybenzofuran-2-yl)-2H-pyran-2-one (118 mg) and 5-hydroxymethylpyrimidine (202 mg) in THF (30 ml) at 0 C., and the mixture was stirred at room temperature overnight. The reaction solution was cooled on ice, a 1 N lithium hydroxide aqueous solution (5 ml) was added and the mixture was stirred at room temperature for one hour, after which the reaction solution was again cooled on ice, a 1 N hydrochloric acid aqueous solution (5 ml) and AcOEt were added, the organic layer and aqueous layer were separated, and the aqueous layer was further extracted with AcOEt. The organic layers were combined and dried with MgSO4, and then filtered and concentrated. The residue was purified by silica gel column chromatography (AcOEt/MeOH=10/1) to obtain 3,5-dimethyl-4-hydroxy-6-(5-(5-pyrimidinylmethoxy)benzofuran-2-yl)-2H-pyran-2-one. Yield: 35 mg (y. 26%) 1H NMR(delta ppm, DMSO-d6): 1.95(s, 3H), 2.29(s, 3H), 5.24(s, 2H), 7.12 to 7.14(m, 1H), 7.33 to 7.38(m, 2H), 7.61 to 7.63(m, 1H), 8.95(s, 2H), 9.18(s, 1H), 10.91(brs, 1H)

According to the analysis of related databases, 25193-95-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Teijin Limited; Microbial Chemistry Research Foundation; US6589984; (2003); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 13223-25-1, 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. 13223-25-1, name is 2-Chloro-4,6-dimethoxypyrimidine, molecular formula is C6H7ClN2O2, 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.

Preparation of methyl 2-(4,6-dimethoxy-2-pyrimidinyloxy) benzoate 4.38 g (25 mmol) of 2-chloro-4,6-dimethoxypyrimidine, 3.80 g (25.0 mmol) of methyl 2-hydroxybenzoate and 0.66 g (6.3 mmol) of sodium methanesulfinate were heated in the presence of 5.17 g (37.5 mmol) of potassium carbonate in 25 ml of N,N-dimethylformamide to 120 C. with stirring. After 1.5 hours, the solvent was removed in a rotary evaporator at 60 C./20 mbar. The residue was taken up in 30 ml of water and 30 ml of dichloromethane. After the organic phase had been separated off, the aqueous phase was again extracted with 20 ml of dichloromethane. The combined organic phases was washed with water, dried over magnesium sulfate and evaporated. The residue was purified by chromatography on a silica gel column (eluent hexane/ethyl acetate 4:1). The title product was obtained from the product fraction in a yield of 5.76 g (77.0 percent of theory) (GC content 97 percent). The melting point of the title compound was 106.7 C. to 108.3 C.

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 13223-25-1, 2-Chloro-4,6-dimethoxypyrimidine.

Reference:
Patent; Lonza AG; US5840892; (1998); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia