Category: pyrimidines

Application of 13754-19-3, 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. 13754-19-3, name is Pyrimidine-4,5-diamine. A new synthetic method of this compound is introduced below.

A mixture OF 4, 5-DIAMINOPYRIMIDINE (1.0 g, 9.1 MMOL), N-(5-butoxycarbonyl)-4- piperidone (3.0 g, 15 mmol) and sodium triacetoxyborohydride (1.2 g, 5.6 mmol) in dichloroethane (60 mL) was stirred at room temperature for 3 d. The reaction was partitioned between chloroform (200 mL) and 3N sodium hydroxide (30 ML). After drying over magnesium sulfate, the organic phase was concentrated to give the title compound as a tan gum. MS 294 (M+1)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13754-19-3, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2004/92166; (2004); A2;,
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Pyrimidine – Wikipedia

Application of 145783-15-9, Adding some certain compound to certain chemical reactions, such as: 145783-15-9, name is 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine,molecular formula is C7H9Cl2N3S, 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 145783-15-9.

It has been verified that using the salts according to the invention with the purity of at least 96 % ee makes it possible to obtain, in any of the further steps of the synthesis of ticagrelor, the final product containing less than 0.15 % of the isomeric impurity IV with a configuration derived from the undesired diastereoiso ier la, without the necessity to use chromatographic purification.The salts of compound I with D-(-)-mandelic and R-(-)-3-chloromandelic acid in the purities mentioned in Examples 1 and 2 were used for the preparation of ticagrelor, which is illustrated in Scheme 1. The salts of the compound I with the said acids are marked I * HA therein. ticagrelorSCHEME 1Abbreviations used:CBz = benzyloxycarbonyl,MIBK methyl isobutyl ketone,DIPEA diisopropylethylamine.The total yield of the method described in Scheme 1 was 16 %. The quality of the obtained product was determined using the liquid chromatography method and amounted to 99.5 % with the content of impurity IV lower than 0.1 %. The method of preparation of ticagrelor according to Scheme 1 did not require the use of chromatographic purification in any of the steps of its synthesis.

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. 145783-15-9, 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ZENTIVA, K.S.; LUSTIG, Petr; HEJTMANKOVA, Ludmila; WO2012/142983; (2012); A1;,
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Synthetic Route of 6693-08-9, Adding some certain compound to certain chemical reactions, such as: 6693-08-9, name is 2,4,6-Trichloro-5-fluoropyrimidine,molecular formula is C4Cl3FN2, 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 6693-08-9.

Part A: (1 S,4S)-2-(2-Chloro-5-fluoro-6-hydrazino-4-pyrimidinyl)-5-methyl-2,5- diazabicyclo[2.2.1]heptane. 2,4,6-Trichloro-5-fluoropyrimidine (2.01 g, 10 mmol) was dissolved in 30 mL of DMSO and stirred at room temperature. Commercially-available (1 S,4S)-2-methyl-2,5- diazabicyclo[2.2.1]heptane, dihydrobromide (2.74 g, 10 mmol) was added, followed by DIPEA (5.51 mL, 32 mmol). The resulting reaction mixture was stirred for 2.5 h, and then hydrazine was added (3.0 mL) and the contents were stirred at room temperature overnight. The reaction mixture was then purified by RP-HPLC to provide the assumed (1 S,4S)-2-(2-chloro-5-fluoro-6-hydrazino-4-pyrimidinyl)-5-methyl-2,5- diazabicyclo[2.2.1]heptane (first eluent), as well as the assumed 4-chloro-5-fluoro-6- [(1 S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]hept-2-yl]-2(1 H)-pyrimidinone hydrazone (second eluent).

According to the analysis of related databases, 6693-08-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/61879; (2009); A1;,
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Adding a certain compound to certain chemical reactions, such as: 3543-46-2, 5-Bromo-4-phenylpyrimidine, 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, 3543-46-2, blongs to pyrimidines compound. Recommanded Product: 5-Bromo-4-phenylpyrimidine

Example 186 methyl 4-methyl-1-(4-phenylpyrimidin-5-yl)piperidine-4-carboxylate A degassed mixture of 5-bromo-4-phenylpyrimidine (600 mg), methyl 4-methylpiperidine-4-carboxylate hydrochloride (520 mg), Pd2(dba)3 (120 mg), Xantphos (150 mg), sodium tert-butoxide (620 mg) and 1,4-dioxane (20 mL) was stirred with microwave irradiation at 110C for 9 hr. The mixture was filtered through silica gel (NH, ethyl acetate), and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (130 mg). 1H NMR (300 MHz, CDCl3) delta 1.22 (3H, s), 1.41-1.54 (2H, m), 2.06-2.15 (2H, m), 2.68-2.79 (2H, m), 2.98-3.08 (2H, m), 3.69 (3H, s), 7.39-7.51 (3H, m), 8.01-8.07 (2H, m), 8.39 (1H, s), 8.89 (1H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3543-46-2, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; KOIKE, Tatsuki; KAJITA, Yuichi; YOSHIKAWA, Masato; IKEDA, Shuhei; KIMURA, Eiji; HASUI, Tomoaki; NISHI, Toshiya; FUKUDA, Hiromi; EP2933247; (2015); A1;,
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Related Products of 4316-94-3, Adding some certain compound to certain chemical reactions, such as: 4316-94-3, name is 6-Chloro-5-nitropyrimidin-4-amine,molecular formula is C4H3ClN4O2, 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 4316-94-3.

General procedure: 6-Chloro-5-nitropyrimidine-4-amine (0.5mmol), amine (1.5mmol), Pd2(dba)3 (0.01mmol), R-BINAP (0.03mmol) and potassium carbonate (0.7mmol) were dissolved in acetonitrile (5mL). The solution was stirred at room temperature for 3.5h under an argon atmosphere. The resulting reaction mixture was treated with saturated brines (50mL) and extracted with acetonitrile (3×25mL), and dried with anhydrous Na2SO4. The anhydrous Na2SO4 was removed by filtration and the filtrate was concentrated. The residue was washed with ethyl acetate (3×2mL) and diethyl ether (3×2mL), filtered and dried under vacuum.

According to the analysis of related databases, 4316-94-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Meng-Meng; Mei, Qiong; Zhang, Yi-Xiao; Bai, Peng; Guo, Xiang-Hai; Chinese Chemical Letters; vol. 28; 3; (2017); p. 583 – 587;,
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Adding a certain compound to certain chemical reactions, such as: 39551-54-7, 2,4-Dichloropyrido[3,2-d]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, 39551-54-7, blongs to pyrimidines compound. Product Details of 39551-54-7

2,4,-dichloropyrido[3,2-d]pyrimidine (163 mg, 0.82 mmol, 1.1 equiv.) was dissolved in dioxane (6 mL), N,N-diisopropylethylamine (0.53 mL, 2.9 mmol, 4 equiv.) and (R)-methyl 2-amino-6-fluorohexanoate 74C (205 mg, 0.74 mmol, 1 equiv.). The reaction mixture was stirred for 1 h and then the mixture of 74D used directly. LCMS (m/z): 326.80 [M+H]+; tR=1.04 min. on LC/MS Method A.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,39551-54-7, its application will become more common.

Reference:
Patent; Gilead Sciences, Inc.; Aktoudianakis, Evangelos; Chin, Gregory; Mackman, Richard L.; Metobo, Samuel E.; Mish, Michael R.; Pyun, Hyung-jung; Zablocki, Jeff; (175 pag.)US2016/289229; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1053228-29-7, 2,4-Dichloro-5-fluoro-7H-pyrrolo[2,3-d]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, 1053228-29-7, blongs to pyrimidines compound. Product Details of 1053228-29-7

To a stirred solution of 2,4-dichloro-5-fluoro-7H-pyrrolo[2,3-Patent; MERCK SHARP & DOHME CORP.; MERCK SHARP & DOHME LIMITED; GIRIJAVALLABHAN, Vinay, M.; MCLAUGHLIN, Mark; CLEATOR, Edward; KONG, Jongrock; GIBSON, Andrew William; LIEBERMAN, David, R.; DIEGUEZ VAZQUEZ, Alejandro; KEEN, Stephen Philip; WILLIAMS, Michael, J.; MOORE, Jeffrey, C.; MILCZEK, Erika, M.; PENG, Feng; BELYK, Kevin, M.; SONG, Zhiguo Jake; (70 pag.)WO2017/53216; (2017); A2;,
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Related Products of 16019-31-1, 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 16019-31-1, name is 5-Allyl-4,6-dichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

[0108] 5-Allyl-4r6-dichloropyrimidine (see Montgomery, J.A. and Hewson, K., J. Med. C em. 1967, 10, 665-667) (2.00 g, 10.6 mmol) was dissolved in THF (16 mL). Osmium tetraoxide (30 mg, 0.10 mmol) was added and after a few min, the reaction mixture turned very dark. Sodium metaperiodate (4.75 g, 22.2 mmol) was then added in portions over 34 min and the reaction mixture temperature was maintained at 20-22 C. The solids were removed by filtration and were washed well with THF (2×5 mL). Saturated brine was added to the filtrate and the phases were separated. The aqueous phase was saturated with solid sodium chloride and the phases separated. The aqueous phase was extracted with additional EtOAc (2 x10 mL). The organic extracts were combined and concentrated under reduced pressure. The crude residue was dried in vacuo and the title compound was isolated as a gray solid (2.00 g, 99% yield). 1H N R (300 MHz, CDCI3) delta 9.80 (s, 1 H), 8.74 (s, 1 H) and 4.14 (s, 2H).

According to the analysis of related databases, 16019-31-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; AMIDON, Benjamin, S.; CARDIN, David, P.; GOULD, Alexandra, E.; GREENSPAN, Paul, D.; HARRISON, Sean, J.; WO2014/22744; (2014); A1;,
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Application of 23002-51-9, Adding some certain compound to certain chemical reactions, such as: 23002-51-9, name is 6-Chloro-1H-pyrazolo[3,4-d]pyrimidine,molecular formula is C5H3ClN4, 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 23002-51-9.

To a mixture of 6-chloro-1H-pyrazolo[3,4-d]pyrimidine (2.0 g, 12.9 mmol), potassium carbonate (3.6 g, 25.9 mmol) in N,N-dimethylformamide (20 mL) was added 2-(trimethylsilyl)ethoxymethyl chloride (2.6 g, 15.5 mmol). The reaction mixture was stirred at 25 C. for 2 h and poured into water (100 mL). The resulting mixture was extracted with ethyl acetate (3*100 mL). The combined organic layers were washed with water (100 mL), brine (100 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 100-200 mesh, 0 to 20% ethyl acetate in petroleum ether) to afford 6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-d]pyrimidine (2.8 g, 76%) as a yellow oil. LCMS RT=2.112 min, m/z=285.2 [M+H]+ ECMS (0 to 60% acetonitrile in water+0.03% trifluoroacetic acid over 2 mins) retention time 2.112 mm, ESI+ found [M+H]=285.2.

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. 23002-51-9, 6-Chloro-1H-pyrazolo[3,4-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Genentech, Inc.; Patel, Snahel; Hamilton, Gregory; (73 pag.)US2018/170927; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
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. 26830-94-4, name is 2,6-Dichloropyrimidine-4-carbonyl chloride. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C5HCl3N2O

General procedure: 2-Aminothiazole (1 g, 0.01 mol), DMAP (80 mg) and TEA (4 ml) were dissolved in THF (30 ml), and compound 7 (4.2 g, 0.02 mol) in THF (30 ml) was added dropwise with stirring. The mixture was stirred until 2-aminothiazole was disappeared. The mixture was filtered, and the solvent was removed in vacuo. Crude products were purified by flash chromatography on silica gel and yellow solid (compound 8, 550 mg) was obtained, yield 20%.

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, 26830-94-4, 2,6-Dichloropyrimidine-4-carbonyl chloride.

Reference:
Article; Zhang, Leilei; Hu, Shengquan; Lei, Lei; Zhang, Yuliang; Zhang, Lijing; Song, Hongrui; Shen, Zhufang; Feng, Zhiqiang; Letters in drug design and discovery; vol. 14; 3; (2017); p. 252 – 261;,
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