Pyrimidines

Adding a certain compound to certain chemical reactions, such as: 4994-86-9, 4-Chloro-2-methylpyrimidine, 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, Quality Control of 4-Chloro-2-methylpyrimidine, blongs to pyrimidines compound. Quality Control of 4-Chloro-2-methylpyrimidine

A solution of 4-chloro-2-methylpyrimidine (100 mg, 0.778 mmol), 2-bromo- 5-fluoroisonicotinonitrile (156 mg, 0.778 mmol) and 1,1,1,2,2,2- hexamethyldistannane (255 mg, 0.778 mmol) in 1,4-dioxane (2 mL) was purged with nitrogen gas for 10 min. Pd(Ph3P)4 (90 mg, 0.078 mmol) was added to the reaction mixture and the solution was purged with nitrogen gas again for 10 min. The reaction mixture was heated in a microwave at 150 C for 2 h. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in ethyl acetate (20 mL) and water (20 mL). The biphasic mixture was filtered through diatomaceous earth (Celite). The bed was washed with ethyl acetate (25 mL). The organic layer was separated, dried over Na2S04, filtered, and concentrated under reduced pressure. The brown solid was purified by silica gel chromatography (0- 40% EtOAc in pet ether) to afford 5-fluoro-2-(2-methylpyrimidin-4-yl) isonicotinonitrile (40 mg, 0.187 mmol, 24% yield) as an off-white color solid. LCMS (ESI) m/e 215.2 [(M+H)+, calcd for CnH8FN4 215.2]; LC/MS retention time (Method Al): = 1.76 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4994-86-9, 4-Chloro-2-methylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BRONSON, Joanne J.; CHEN, Ling; DITTA, Jonathan L.; DZIERBA, Carolyn Diane; JALAGAM, Prasada Rao; LUO, Guanglin; MACOR, John E.; MAISHAL, Tarun Kumar; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; SISTLA, Ramesh Kumar; THANGAVEL, Soodamani; (485 pag.)WO2017/59085; (2017); A1;,
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Synthetic Route of 287714-35-6, Adding some certain compound to certain chemical reactions, such as: 287714-35-6, name is Methyl 2-chloropyrimidine-5-carboxylate,molecular formula is C6H5ClN2O2, 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 287714-35-6.

To a stirred solution of methyl 2-chloropyrimidine-5-carboxylate (5 g, 28.97 mmol) in dry DMF (60 mL), TEA (12.09 mL, 86.92 mmol) and tert-butyl piperazine-1-carboxylate (5.93 g, 31.87 mmol) were added at 0 C. The reaction mixture was heated at 100 C overnight. Itwas concentrated to half of the volume and filtered. The resulting solid was dissolved inDCM (35 mL) and washed with water (20 mL), dried over Na2SO4 and concentratedaffording the title product. Yield: 70% (7 g, off white solid). 1H NMR (400 MHz, DMSO-d6):6 8.81 (5, 2H), 3.84 (t, J = 4.8 Hz, 4H), 8.80 (5, 3H), 3.48-3.38 (m, 4H), 1.42 (5, 9H). LCMS:(Method A) 323.3 (M+H), Rt. 4.31 mm, 99.89% (Max).

According to the analysis of related databases, 287714-35-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; KULKARNI, Santosh, S.; GIRI, Awadut, Gajendra; (280 pag.)WO2017/144633; (2017); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 89581-38-4, Methyl 5-bromopyrimidine-2-carboxylate, 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, Product Details of 89581-38-4, blongs to pyrimidines compound. Product Details of 89581-38-4

Under the protection of N2, PdCl2(dppf) (0.337 g, 0.461 mmol) was added to an anhydrous 1,4-dioxane (200 mL) solution of methyl 5-bromo-2-pyrimidinecarboxylate (2.00g, 9.22 mmol), bis(pinacolato)diboron (2.80 g, 11.1 mol) and anhydrous potassium acetate (2.70 g, 27.7 mol), and the resulting mixture was heated to 100C to react overnight. After cooling and concentration under reduced pressure, water and ethyl acetate were added to the residue, stirred for 15 min, and filtered through Celite filler, and the Celite filler was rinsed with ethyl acetate. After the filtrate was layered, the aqueous phase was extracted with ethyl acetate once. The ethyl acetate phases were combined, washed with a saturated sodium chloride aqueous solution, dried with anhydrous sodium sulfate, and concentrated to obtain a brownish black residue. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (5:1) to obtain a white solid product (1.47 g, 60%). 1H NMR (400 MHz, CDCl3) delta 9.19 (s, 2H), 4.10 (s, 3H), 1.39 (s, 12H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89581-38-4, Methyl 5-bromopyrimidine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co.,Ltd; Centaurus BioPharma Co., Ltd.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; LI, Jijun; WU, Wei; ZHU, Yan; WANG, Huting; ZHAO, Lijia; HE, Weinan; SUN, Yinghui; PENG, Yong; HAN, Yongxin; (108 pag.)EP3412669; (2018); A1;,
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Pyrimidine – Wikipedia

Application of 13036-57-2, 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. 13036-57-2, name is 2-Chloro-4-methylpyrimidine, molecular formula is C5H5ClN2, 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.

General procedure: 2-Chloro-4,6-disubstituted-pyrimidines 17 were prepared bythe reaction of the diazoniumsalts of 4,6-disubstituted-pyrimidin-2-amines (16) with concentrated hydrochloric acid and ZnCl2 [35].Compound 18 was prepared according to literature [32], and themethod was improved. To a stirred solution of piperazine(45 mmol) and K2CO3 (16.5 mmol) in water (20 mL) was addedchloropyrimidine 17 (18 mmol) in small portions at 50e65 C. Themixture was stirred for 1 h at 60e65 C and cooled to 35 C. Theyellowsolid, 1,4-bispyrimidylpiperazine byproduct, was filtered off,and the filtrate was then extracted three times with chloroform,dried over Na2SO4, and evaporated in vacuum to give compound 18,which was used for the following reactions without further purification.

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 13036-57-2, 2-Chloro-4-methylpyrimidine.

Reference:
Article; Wang, Bao-Lei; Shi, Yan-Xia; Zhang, Shu-Jun; Ma, Yi; Wang, Hong-Xue; Zhang, Li-Yuan; Wei, Wei; Liu, Xing-Hai; Li, Yong-Hong; Li, Zheng-Ming; Li, Bao-Ju; European Journal of Medicinal Chemistry; vol. 117; (2016); p. 167 – 178;,
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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.90905-33-2, name is 2-Methylpyrimidine-5-carbaldehyde, molecular formula is C6H6N2O, molecular weight is 122.1246, as common compound, the synthetic route is as follows.Product Details of 90905-33-2

Int-12A. 3-Amino-3-(2-methylpyrimidin-5-yl)propanoic acid: A mixture of commercially available 2-methylpyrimidine-5-carbaldehyde (1.00 g, 8.19 mmol), malonic acid (1.28 g, 12.3 mmol) and ammonium acetate (1.58 g, 20.5 mmol) in EtOH (6.55 mL) were heated to 80 C for 4 h. The reaction mixture was cooled to rt and the precipitate was collected by filtration, washed with cold EtOH and dried under vacuum to yield Int- 12A (1.08 g, 73%) as an off- white solid which was used in the next step without further purification. NMR (500 MHz, D20) delta 8.79 (s, 2H), 4.75 – 4.73 (m, 1H), 3.01 – 2.92 (0451) (m, 1H), 2.90 – 2.82 (m, 1H), 2.70 (s, 3H). HPLC retention time (Method 2): 0.168 mia; LCMS (ES): m/z 182.1 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,90905-33-2, 2-Methylpyrimidine-5-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHAO, Guohua; MIGNONE, James; (117 pag.)WO2018/89360; (2018); A1;,
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Pyrimidine – Wikipedia

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 4595-61-3, name is Pyrimidine-5-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C5H4N2O2

(R)-4-{l-[(l-Amino-cyclopropanecarbonyl)-amino]-ethyl}-benzoic acid methyl ester (74.5 mg, 0.284 mmol) was added to a stirred solution of pyrimidine-5-carboxylic acid (42.3 mg, 0.341 mmol), HATU (129.6 mg, 0.341 mmol) and DIPEA (247.3 muL, 1.420 mmol) in DMF (2 mL). After stirring overnight the reaction mixture was concentrated in vacuo and the residue was partitioned between EA (30 mL) and sat. NaHCO3 solution (50 mL). After extraction of the aqueous layer with EA (2 x 30 mL) the combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to give the title compound which was used for the next reaction without further purification. MS (m/z): 368.9 [M+H*]

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, 4595-61-3, Pyrimidine-5-carboxylic acid.

Reference:
Patent; JERINI AG; WO2009/36996; (2009); A2;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 33034-67-2, 2-Chloro-4-(trifluoromethyl)pyrimidine, 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, name: 2-Chloro-4-(trifluoromethyl)pyrimidine, blongs to pyrimidines compound. name: 2-Chloro-4-(trifluoromethyl)pyrimidine

tert-Butyl 2-cyano-2-[4-trifluoromethylpyrimidin-2 (1H)-ylidene]acetate. tert-Butyl 2-cyanoacetate (97.45 g, 690 mmol) was dissolved in anhydrous THF (1 L), and cooled on an ice-bath for 90 min with stirring under nitrogen. A 1M solution of lithium hexamethyldisilazane in THF (690 mL, 690 mmol) was added dropwise. The mixture was stirred for an additional 1 hr, then 2-chloro-4-trifluoromethylpyrimidin (105 g, 590 mmol) was added dropwise. The mixture was then heated to 50° C. for 3 hr with stirring under nitrogen, allowed to cool, and the solvent removed under reduced pressure. Hydrochloric acid (1N) was added to the residue to achieve a pH of 1-2. The precipitated solids were collected by filtration and dried under vacuum to give tert-butyl 2-cyano-2-[4-trifluoromethylpyrimidin-2(1H)-ylidene]acetate (135 g, 82percent yield) as a bright yellow solid, >98percent pure by LC/MS. tert-Butyl 2-cyano-2-[4-trifluoromethylpyrimidin-2(1H)-ylidene]acetate (48 g; 166 mmol) was suspended in 4M hydrogen chloride in dioxane (415 mL, 1.66 mol) and the mixture stirred at room temperature for 6 hr, then concentrated under reduced pressure to give 2-(4-trifluoromethylpyrimidin-2-yl)acetonitrile (31 g, 100percent yield) as an orange oil, >98percent pure by LC/MS. To a stirred solution of 2-(4-trifluoromethylpyrimidin-2-yl)acetonitrile (31.0 g; 166 mmol) in absolute ethanol (800 mL) was added potassium O-ethylxanthate (26.6 g; 166 mmol) followed by potassium carbonate (45.8 g; 332 mmol). The mixture was heated to 100° C. for 3 hr, cooled to room temperature, iodomethane (47.1 g; 332 mmol) added dropwise, and 1N hydrochloric acid (2 L) added. The resulting mixture was extracted with DCM (1.5 L), and the DCM layer was washed twice with brine (1 L each). The solvent was removed under reduced pressure to give 3,3-bis(methylthio)-2-(4-trifluoromethylpyrimidin-2-yl)acrylonitrile (36 g, 75percent yield) as a light brown solid, >95percent pure by LC/MS.

The synthetic route of 33034-67-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Telik, Inc.; US2010/81653; (2010); A1;,
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Pyrimidine – Wikipedia

Reference of 6299-25-8 , The common heterocyclic compound, 6299-25-8, name is 4,6-Dichloro-2-(methylthio)pyrimidine, molecular formula is C5H4Cl2N2S, 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.

To a stirred solution of 4,6-dichloro-2- (methylthio)pyrimidine (50 g, 0.26 mol) in dichloromethane (1 L) at 00C was added meta-chloroperoxybenzoic acid (143.6 g, 0.64 mol) over a period of 20 minutes. The solution was allowed to warm to room temperature and was stirred for 4 hours. The mixture was diluted with dichloromethane (1.5 L) and then treated sequentially with 50% Na2S2O3 / NaHCO3 solution (2 x 200 ml), sat. NaHCO3 solution (4 x 300 ml), and brine (200 ml) then dried (MgSO4). The solvent was removed in vacuo to afford an off-white solid, which was redissolved in EtOAc (IL) and treated sequentially with sat. NaHCO3 solution (3 x 300 ml), and brine (100 ml) then dried (MgSO4). The solvent was removed EPO in vacuo to afford the title compound (A) as a white solid (55.6 g, 96% yield). 1H NMR CDCl3 delta 3.40 (3H5 s, CH3), 7.75 (IH. s. ArH).

The synthetic route of 6299-25-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2007/14250; (2007); A2;,
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Pyrimidine – Wikipedia

Related Products of 1208901-69-2, Adding some certain compound to certain chemical reactions, such as: 1208901-69-2, name is 2,4-Dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine hydrochloride,molecular formula is C7H8Cl3N3, 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 1208901-69-2.

Compound (D) (11.8 g, 49.1 mmol) prepared in Step 3 was dissolved in dichloromethane (300 mL), then cyclopropanecarbonyl chloride (5.4 mL, 1.2 equivalents) and triethylamine (20.4 mL, 3.0 equivalents) were added thereto and the mixture was stirred at room temperature for 1 hour. The resulting reaction solution was washed with water and a saturated sodium bicarbonate solution and dried over magnesium sulfate. After evaporating the solvent, diisopropyl ether was added to the residue and the suspension was stirred for not shorter than 1 hour. After that, the crystals separated out therefrom were filtered and dried in vacuo to prepare compound (E) (12.5 g, yield: 94%).

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. 1208901-69-2, 2,4-Dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KYOWA HAKKO KOGYO CO., LTD.; EP1537879; (2005); A1;,
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Pyrimidine – Wikipedia

Reference of 22536-61-4, 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.22536-61-4, name is 2-Chloro-5-methylpyrimidine, molecular formula is C5H5ClN2, molecular weight is 128.56, as common compound, the synthetic route is as follows.

To a solution of 2-chloro-5-methyl-pyrimidine (500.00 mg, 3.89 mmol, 1.00 eq) in MeOH (10.00 mL) and DMF (2.00mL) was added triethylamine (1.18 g, 11.67 mmol, 1.62 mL, 3.00 eq) and Pd(dppf)C12 (426.87 mg, 583.39 umol, 0.15 eq) under CO. The suspension was degassed and purged with CO several times. The mixture was stirred under CO (3 Mpa) at 120C for 16 h. The reaction mixture was filtered and the filtrate was concentrated. The crude residue was purified by column chromatography (Petroleum ether : Ethyl acetate=20: l to 0: 1) to afford methyl 5-methylpyrimidine-2-carboxylate (350.00 mg). LCMS (M+H+) m/z: 153.

Statistics shows that 22536-61-4 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-methylpyrimidine.

Reference:
Patent; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; AUDIA, James, Edmund; COTE, Alexandre; DUPLESSIS, Martin; GEHLING, Victor, S.; HARMANGE, Jean-christophe; VASWANI, Rishi, G.; (274 pag.)WO2016/172496; (2016); A1;,
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