Pyrimidines

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. 784150-41-0, name is 6-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H3BrClN3, 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. Application In Synthesis of 6-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

To a solution of aryl bromide (233 mg, 1.0 mmol) in 1,4- dioxane (8 mL) and H2O (2 mL) was added tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl)-5,6-dihyropyridine-1(2H)-carboxylate (Eunkyung, K. et al Bioorganic & Medicinal Chemistry Letters 2008, 18, 4993-4996) (245 mg, 0.8 mmol), Pd(dppf)Cl2.DCM (41 mg, 0.05 mmol) and K2CO3(276 mg, 2.0 mmol) under N2. The mixture was stirred at 110 C for 4 h, cooled to rt, diluted with H2O (80 mL) and extracted with EtOAc (60 mL x 3 . The organic layers separated, dried (Na2SO4) concentrated in vacuo to afford a residue which was purified by column chromatography (petroleum ether/EtOAc = 5:1 to 2:1) to give the title compound (77 mg, yield 23%) as yellow solid ESI-MS (M+H)+: 335.2.1H NMR (400 MHz, CDCl3) : 10.82 (br, 1H), 8.71 (s, 1H), 6.73 (s, 1H), 6.68-6.56 (m, 1H), 4.16-4.13 (m, 2H), 3.70-3.65 (m, 2H), 2.62-2.60 (m, 2H), 1.46 (s, 9H).

With the rapid development of chemical substances, we look forward to future research findings about 784150-41-0.

Reference:
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian T.; MA, Bin; CHAN, Timothy Raymond; KUMARAVEL, Gnanasambandam; MIAO, Hua; BERTOLOTTI-CIARLET, Andrea; OTIPOBY, Kevin; WO2015/89327; (2015); A1;,
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Synthetic Route of 3764-01-0, Adding some certain compound to certain chemical reactions, such as: 3764-01-0, name is 2,4,6-Trichloropyrimidine,molecular formula is C4HCl3N2, 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 3764-01-0.

2,4,6-trichloropyrimidine (8) 10.00 g, 54.52 mmol) was added to a 250 mL three-necked flask.Add 100mL of dichloroMethane, stirred and dissolved, added DIEA (8.50 mL, 48.70 mmol), cooled to -78 C, slowly added morpholine (4.30 mL,49.40mmol), after adding, the reaction was stirred for 1 to 2 hours, TLC (petroleum ether: ethyl acetate = 6:1) was used to detect the reaction of the starting material 8 and the reaction was stopped. The reaction solution was poured into 150 mL of water, and the mixture was separated. Methyl chloride layer, the aqueous layer was extracted with 50 mL of dichloromethaneThe methylene chloride layer was combined and washed twice with saturated sodium chloride solution (80 mL¡Á2), dried over anhydrous Na 2 SO 4 , filtered and filtered.The crude product was obtained by adding a mixed solvent (petroleum ether: ethyl acetate = 50:1, 100 mL) for 2 hours, suction filtration, and drying to give a white solid.The body was 9.4 g, and the yield was 73.7%.

According to the analysis of related databases, 3764-01-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; China Pharmaceutical University; Hefei Medical Engineering Pharmaceutical Co., Ltd.; Xu Yungen; Zhu Qihua; Wang Junwei; Chu Zhaoxing; Li Hui; Ge Yiran; He Guangwei; (22 pag.)CN109810100; (2019); A;,
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Related Products of 13479-88-4, 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 13479-88-4, name is 5,7-Dichlorothiazolo[5,4-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 5,7-dichlorothiazolo[5,4-d]pyrimidine (300 mg, 1.46 mmol), 4-(1H- pyrazol-4-yl)aniline (233, 1.46 mmol), and iPr2NEt (0.51 mL, 2.93 mmol) in DIVIF (2.9 mL) was heated at 100 C for 5h, cooled to rt, and diluted with water. The precipitate formed was collected by filtration and washed with water and dried in vacuo to provide the title compound (470 mg, 98%). MS (ES+) m/e 329 (M+H).

According to the analysis of related databases, 13479-88-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KADMON CORPORATION, LLC; OLSZEWSKI, Kellen; POYUROVSKY, Masha; BARSOTTI, Anthony; KIM, Ji-In; LIU, Kevin; MORRIS, Koi; (143 pag.)WO2016/210331; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 148550-51-0, Ethyl 2-(methylsulfonyl)pyrimidine-5-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, SDS of cas: 148550-51-0, blongs to pyrimidines compound. SDS of cas: 148550-51-0

Title compound 201 (0.250 g, 0.741 mmol), ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate (0.122 g, 0.529 mmol), potassium carbonate (0.280 g, 2.645 mmol) and DME (5 mL) were combined. The reaction mixture was stirred at 50¡ã C. for 2 hours. The mixture was cooled down and quench with water. The aqueous layer was extracted twice with ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and evaporated. The crude was purified by flash chromatography eluting with 0percent to 30percent ethyl acetate in hexanes to afford title compound 202 (0.141 g, 64percent). LRMS (ESI): (calc) 414.21 (found) 415.0 (MH)+.

The synthetic route of 148550-51-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Forum Pharmaceuticals, Inc.; Rogers, Kathryn; Patzke, Holger; (315 pag.)US2017/749; (2017); A1;,
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Synthetic Route of 34171-40-9, 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. 34171-40-9, name is 2,4-Dichloro-5-ethylpyrimidine. A new synthetic method of this compound is introduced below.

Preparation of 2-chloro-5-ethyl-4-(4-methoxybenzyloxy)pyrimidineIn a round bottom flask, (4-methoxyphenyl)methanol (859 mg) and lithium f-butoxide (453 mg) are stirred in THF (5.65 ml_) at 70 C for 15 minutes and then cooled to room temperature. In a separate flask, 2,4- dichloro-5-ethylpyrimidine (1.00 g) is dissolved in DMF (10 ml_) and this solution is than transferred dropwise (over 30 minutes) to the previous mixture at 0 C and then let warmed to room temperature. After 3 hours, the reaction proved to be completed by GC-MS with an isomers ratio of ~ 18 / 1. Reaction mixture diluted with ethyl acetate and washed twice with water, once with brine, dried over sodium sulfate, filtered and concentrated to afford the crude. The residue was purified by flash column chromatography (S1O2, 5%-30% ethyl acetate / heptane) to provide 2-chloro-5-ethyl-4-(4- methoxybenzyloxy)pyrimidine (787 mg, 50%) as a colorless oil (Isomers ratio after purification ~ 32 / 1 ). MS (M+1 ): 279.0. 1H NMR (400 MHz, CDCI3) delta ppm 1.16 (m, J=7.43, 7.43 Hz, 3 H), 2.52 (q, J=7.62 Hz, 2 H), 3.81 (s, 3 H), 5.37 (s, 2 H), 6.85 – 6.95 (m, 2 H), 7.34 – 7.43 (m, 2 H), 8.10 (s, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,34171-40-9, 2,4-Dichloro-5-ethylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; ASPNES, Gary Erik; DIDIUK, Mary Theresa; GUZMAN-PEREZ, Angel; MAGUIRE, Robert John; WO2011/158149; (2011); A1;,
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Synthetic Route of 3435-25-4, 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. 3435-25-4, name is 4-Chloro-6-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.

[0484] Procedure: To a stirred solution of compound (2-(piperidin-4-yl)ethyl)sulfamide hydrochloride (0.1 g, 0.41 mmol) in DMF (4 mL) was added 4-chloro-6-methylpyrimidine (0.058 g, 0.45 mmol) and aqueous solution of potassium carbonate (0.113 g, 0.82 mmol) and the resulting reaction mixture was stirred at 90 C for 12 h. The progress of the reaction was monitored by TLC. Then the reaction was quenched with water (20 mL) and extracted with ethyl acetate (2 ¡Á 30 mL). The combined organic layers were washed with brine (30 mL), dried over sodium sulphate, filtered and evaporated under reduced pressure. The crude obtained was purified by combiflash purifier using ethyl acetate in n-hexane to afford N-(2-(1-(6-methylpyrimidin-4-yl)piperidin-4-yl)ethyl)sulfamide (0.011 g , 11.4 %). 1HNMR (400 MHz, DMSO-d6): delta 8.31-(s, 1H), 6.65 (s, 1H), 6.42 (s, 2H), 6.36-6.39 (m, 1H), 4.30-4.40 (m, 2H), 2.89 (q, J = 7.2 Hz, 2H), 2.81-(t, J = 11.2 Hz, 2H), 2.21(s, 3H), 1.62-1.70 (m, 3H), 1.38 (q, J = 7.2 Hz, 2H), 0.96-1.05 (m, 2H). LC-MS (ES) m/z = 300.1 [M+H]+.

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 3435-25-4, 4-Chloro-6-methylpyrimidine.

Reference:
Patent; MAVUPHARMA, INC.; GALLATIN, William Michael; ODINGO, Joshua; DIETSCH, Gregory N.; FLORIO, Vincent; VENKATESHAPPA, Chandregowda; DURAISWAMY, Athisayamani Jeyaraj; (273 pag.)WO2019/46778; (2019); A1;,
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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. 148550-51-0, name is Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate. A new synthetic method of this compound is introduced below., SDS of cas: 148550-51-0

To a stirred solution of Example 13 (1.87 g, 6.94mmol) in dry acetonitrile (10 mL), potassium carbonate (2.87 g, 20.8 mmol, Spectrochem) and ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate (1.6 g, 6.94 mmol, synthesis described in Example 98, steps, 1 and 2) were added. The resulting mixture was stirred at rt for 3 h. It was then filtered through celite and concentrated. The crude product was diluted with dichloromethane (25 mL), washed with water and dried over anhydrous Na2SO4. After evaporation of the solvent, the crude product was purified by flash column chromatography to afford the title compound (white solid). 1H NMR (400 MHz, DMSO-d6): delta 8.74 (s, 1H), 6.78-6.72 (m, 2H), 5.97 (s, 1H), 4.38-4.36 (m, 1H), 3.81 (s, 2H), 2.37-2.47 (m, 9H), 1.26 (d, J = 2.84 Hz, 3H), LCMS: (Method A) 385.2 (M+H), Rt. 3.22 min, 98.6percent (Max).

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, 148550-51-0, Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate.

Reference:
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; KULKARNI, Santosh S.; GIRI, Awadut Gajendra; KOEK, Johannes Nicolaas; (64 pag.)WO2017/144635; (2017); A1;,
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Reference of 55583-59-0, 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. 55583-59-0, name is 2,5-Diamino-4,6-dichloropyrimidine, molecular formula is C4H4Cl2N4, 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.

In the reaction vessel,4,6-Dichloropyrimidine-2,5-diamine(1.00 g, 5.59 mmol), phenylboronic acid(0.681 g, 5.59 mmol), sodium carbonate(2.96 g, 27.9 mmol), and tetrakis(Triphenylphosphine) palladium (0) (323 mg, 0.279 mmol) in toluene (56 mL),Ethanol (14 mL) and distilled water (14 mL)The reaction mixture was cooled to room temperature after stirring for 20 hours under heating reflux conditions under argon atmosphere.Distilled water (6 mL) was added and stirred, and the separated aqueous layer was extracted three times with ethyl acetate (20 mL). Thereafter, the total amount of organic layers is combined, saturated aqueous sodium chloride solution (20 mL) is added thereto, the mixture is stirred for washing, and the separated organic layer is dehydrated by adding anhydrous sodium sulfate,The filtrate after filtration was concentrated under reduced pressure. The concentrate thus obtained is purified by flash column chromatography (silica gel, n-hexane / ethyl acetate),4-Chloro-6-phenylpyrimidine-2,5-diamine was obtained(590 mg, 48% yield).

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 55583-59-0, 2,5-Diamino-4,6-dichloropyrimidine.

Reference:
Patent; Microbial Chemistry Research Foundation; Kumagai, Naoya; Noda, Hidetoshi; Asada, Yasuko; Shibazaki, Masakatsu; (48 pag.)JP2019/64981; (2019); A;,
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Adding a certain compound to certain chemical reactions, such as: 56844-40-7, 6-Bromothieno[2,3-d]pyrimidin-4(3H)-one, 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, 56844-40-7, blongs to pyrimidines compound. Safety of 6-Bromothieno[2,3-d]pyrimidin-4(3H)-one

Compound 5 (1.00 g, 4.33 mmol) was mixed with (2-methoxyphenyl)boronic acid (795 mg, 5.23 mmol), fine powdered K2CO3 (1.44 g, 10.39 mmol), Pd(PPh3)4 (50 mg, 0.04 mmol) and 1/1 1,4-dioxane/water (30 mL). The reaction was then stirred at 110 C for 5 h under nitrogen atmosphere. The solvent was removed and the product was diluted with water (50 mL). The mixture was filtered and the solid material washed with water (2¡Á75 mL). This was used without further purification. Drying gave 1.02 g (3.95 mmol, 91%) of 6 as a light brown solid, mp 317 C (dec.); 1H NMR (400 MHz, DMSO-d6) delta: 12.48 (s br, 1H), 8.12 (s, 1H), 7.85-7.81 (m, 2H), 7.41-7.35 (m, 1H), 7.21-7.16 (m, 1H), 7.08-7.03 (m, 1H), 3.95 (s, 3H); 13C NMR (100 MHz, DMSO-d6) delta: 163.8, 157.2, 155.3, 146.3, 135.3, 129.8, 128.0, 124.6, 121.2, 120.3, 118.6, 112.4, 55.8; IR (neat, cm-1): 3070, 1668, 1456, 1265, 1020, 865, 775, 759; HRMS (APCI/ASAP, m/z): 259.0537 (calcd. C13H11N2O2S, 259.0541, [M+H]+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,56844-40-7, its application will become more common.

Reference:
Article; Bugge, Steffen; Moen, Ingri Ullestad; Kragseth Sylte, Kent-Ove; Sundby, Eirik; Hoff, Bard Helge; European Journal of Medicinal Chemistry; vol. 94; (2015); p. 175 – 194;,
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Electric Literature of 1820-81-1 , The common heterocyclic compound, 1820-81-1, name is 5-Chlorouracil, molecular formula is C4H3ClN2O2, 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.

1-(2′,3′,4′,6′-tetra-O-Acetyl-b-D-glucopyranosyl)-5-chlorouracil (12b). 12b (1.14 g,93%) was obtained as a white amorphous under the following conditions: 5-chlorouracil (487.5 mg, 3.33 mmol), HMDS (3.5 mL), pyridine (1.7 mL), reflux, 30 min.N-Glycosylation: 2b (3.33 mmol), MeCN (25 mL), 11 (1.00 g, 2.56 mmol), 7b (80.5mg, 0.26 mmol, 10 mol%), reflux, 24 h, purification by MPLC (size 120, EtOAc_hexane= 0:100 50:50).

The synthetic route of 1820-81-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shirouzu, Hiroshi; Morita, Hiroki; Tsukamoto, Masaki; Tetrahedron; vol. 70; 22; (2014); p. 3635 – 3639;,
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