Tag: M.W:200-300

Adding a certain compound to certain chemical reactions, such as: 959236-97-6, 4-Bromo-2-(methylthio)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, Safety of 4-Bromo-2-(methylthio)pyrimidine, blongs to pyrimidines compound. Safety of 4-Bromo-2-(methylthio)pyrimidine

A suspension of 4-bromo-2-(methylthio)pyrimidine (9 A, 1.18g, 7.35 mmol) , potassium carbonate (37ml, 0.4 M in water), o-tolylboronic acid (1 g, 7.35 mmol) andtetrakis(triphenylphosphine)palladium(0) (425 mg, 0.37 mmol) in DME (40 ml) was degassed for 20 minutes. It was then heated at reflux for 2 hours. The reaction mixture was cooled and filtered through celite. The filtrate was extracted with EtOAc (2 x 30 ml). The organic layer was dried with Na2S04, filtered and concentrated. The crude product was purified by flash column (Rf: 0.3 10%EtOAc/Hexanes). The yield was 98%. MS (m/z) 217 [M+H]+

The synthetic route of 959236-97-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; BONDY, Steven S.; CANNIZZARO, Carina E.; CHOU, Chien-hung; HALCOMB, Randall L.; HU, Yunfeng Eric; LINK, John O.; LIU, Qi; SCHROEDER, Scott D.; TSE, Winston C.; ZHANG, Jennifer R.; WO2013/6738; (2013); A1;,
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Pyrimidine – Wikipedia

Reference of 1224944-77-7, 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 1224944-77-7, name is Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Into a 50 mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen were placed a solution of ethyl 5-chloropyrazolo1,5-a]pyrimidine-3-carboxylate (300 mg, 1.33 mmol) in N,N-dimethylformamide (20 mL), tert-butyl N-(prop-2-yn-1-yl)carbamate (408 mg, 2.63 mmol), triethylamine (1.8 mL), copper (I) iodide (24 mg, 0.13 mmol), and Pd(PPh3)2Cl2 (47.1 mg, 0.07 mmol). The resulting mixture was stirred for 5 h at room temperature. After concentrated under vacuum, the residue was treated with 30 mL of ethyl acetate. The resulting mixture was washed with 3 x20 mL of water and 2 x 20 mL of sat. ammonium chloride. The organic phase was dried over sodium sulfate, concentrated, and filtered under reduced pressure. This resulted in ethyl 5-(3-[[(tert-butoxy)carbonyl]amino]prop-1-yn-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate as an oil.

According to the analysis of related databases, 1224944-77-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIM, Jongwon; ALTMAN, Michael, D.; CHILDERS, Matthew, L.; GIBEAU, Craig, R.; HO, Ginny Dai; TSUI, Honchung; (80 pag.)WO2016/144844; (2016); A1;,
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Reference of 51940-64-8, Adding some certain compound to certain chemical reactions, such as: 51940-64-8, name is Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate,molecular formula is C7H6Cl2N2O2, 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 51940-64-8.

1.58 g (7.18 mmol) in ACN was added 920 mg (8.6 mmol) p-toluidine and ~2 mL DIE A. The reaction was stirred at room temperature for ~1 hour. The ACN was removed in vacuo until solid precipitated. At this point water (-50 mL) was added and the solid was filtered. The solid (B6.2) was dried and massed to be 1.85 g (89% yield). To 1.01 g (3.47 mmol) of B6.2 in a 50/50 mixture of THF/H20 was added 4.16 mmol of LiOH in H20 (1.2 eq). The reaction was stirred at room temperature for 30 minutes and then was acidified to pH~2 with 1 M HCl (aq). The volatiles were removed and the resulting solid was filtered to give 613 mg B6.2. To B6.2 in DMF was added 662 mg HOBt H20 and 708 mg EDC HCl. After stirring for 2 hours and additional 0.5 eq of EDC HCl was added. The reaction was stirred for 1 hour and then NH3 in dioxane (excess) was added. The reaction was stirred for 45 minutes and then the dioxane was removed in vacuo. Water was added which led to a precipitate. The solid (B6.3) was filtered, washed with water and dried. To -200 mg B6.3 in ~2 mL NMP and 0.3 mL DIEA was added 240 mg (S)-tert-butyl 1 -aminopropan-2-ylcarbamate. The reaction mixture was stirred at 90C for 2 hours and was then cooled. Water was added, solid precipitated and was filtered. Similar to Scheme 2 (example 73), a Boc-deprotection utilizing DCM/TFA afforded the title compound. MS found for C15H2ON6O as (M+H)+301.2.

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. 51940-64-8, Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; JIA, Zhaozhong J.; KANE, Brian; XU, Qing; BAUER, Shawn M.; SONG, Yonghong; PANDEY, Anjali; DICK, Ryan; WO2013/78468; (2013); A1;,
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Pyrimidine – Wikipedia

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. 1032452-86-0, name is 3-(2-Chloropyrimidin-4-yl)-1-methyl-1H-indole. A new synthetic method of this compound is introduced below., category: pyrimidines

P-Toluenesulfonic acid hydrate (22.73 g, 119.5 mmol)Was added to a solution of 3- (2-chloropyrimidin-4-yl) -1-methyl-indole (Intermediate 20, 24.27 g, 99.58 mmol)And 4-fluoro-2-methoxy-5-nitroaniline (Intermediate 22, 18.54 g, 99.58 mmol)In a mixture of 2-pentanol (500 mL).The resulting mixture was stirred at 105 C for 2.5 hours.Then cooled to room temperature.The resulting precipitate was collected by filtration,Washed with 2-pentanol (50 mL), dried under vacuum,Some of the desired product was obtained as a yellow solid. The filtrate was cooled,The resulting precipitate was collected by filtration,Washed with 2-pentanol (10 mL).The two batches were combined and ground with CH? CN to obtain a solid,The solid was collected by filtration, dried under vacuum,The title compound was obtained as a yellow solid (37.4 g, 95%).

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Reference:
Patent; Jiao Yuqi; (53 pag.)CN107043369; (2017); A;,
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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. 1211443-61-6, name is 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 1211443-61-6

50 mL two neck-flask was charged with 2-chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d] pyrimidine-6-carboxamide(835 mg, 2.85 mmol), 2-amino-5-(4-(tertbutoxycarbonyl)piperazin-1-yl) pyridine 1-oxide (840 mg,2.85 mmol), Palladium diacetate(16 mg, 0.071 mmol),BINAP (89 mg, 0.143 mmol), cesium carbonate (1.39 g,4.3 mmol) and 1,4-dioxane (20 mL) and stirred at 100 Cunder inert atmosphere overnihgt. The reaction mixture wasconcentrated and purified by column chromatography toafford the title compound 7 (1.1 g, 68%) as tan solid. 1HNMR (400 MHz, Chloroform-d) delta 9.63 (s, 1H), 8.73 (d, J= 1.3 Hz, 1H), 8.65 (d, J = 9.4 Hz, 1H), 7.95 (d, J = 2.3 Hz,1H), 7.05 (dd, J = 9.5, 2.5 Hz, 1H), 6.46 (d, J = 1.3 Hz,1H), 4.86-4.72 (m, 1H), 3.59 (t, J = 5.0 Hz, 4H), 3.15 (s,6H), 3.06 (t, J = 5.0 Hz, 4H), 2.66-2.43 (m, 2H), 2.15-1.96(m, 4H), 1.85-1.64 (m, 2H), 1.48 (s, 9H). 13C NMR(101 MHz, CDCl3) delta 163.83, 154.53, 153.19, 151.76,151.55, 141.72, 139.75, 132.98, 126.73, 118.85, 113.68,113.18, 100.74, 80.24, 58.01, 49.49, 39.42, 35.20, 30.20,28.41, 24.61.

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, 1211443-61-6, 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide.

Reference:
Article; Guo, Qingxiang; Li, Yongtao; Zhang, Chao; Huang, Zhi; Wang, Xin; Nie, Yongwei; Li, Yao; Liu, Yanhua; Yang, Shengyong; Xiang, Rong; Fan, Yan; Medicinal Chemistry Research; vol. 27; 6; (2018); p. 1666 – 1678;,
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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. 1780-40-1, name is 2,4,5,6-Tetrachloropyrimidine, the common compound, a new synthetic route is introduced below. Formula: C4Cl4N2

(4.408 mmol) of 4- (10H-phenoxazin-10-yl) phenylboronic acid were successively added,(0.92 mmol) of 2,4,5,6-tetrachloropyrimidine,103 mg (0.46 mmol) of palladium acetate,241 mg (0.92 mmol) of triphenylphosphine as well1.17 g (11.04 mmol) of anhydrous potassium carbonate was added100ml three-mouth flask,Then, 50 mL of ethylene glycol dimethyl ether was added as a reaction solvent,Air was removed and refluxed for 24 h.After completion of the reaction, the reaction solvent was distilled off under reduced pressure, and the mixture was extracted three times with DCM and then dried by passing through a column.To give 0.38 g of a yellow solid,Yield 38.6%.

The synthetic route of 1780-40-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dalian University of Technology; Liu, Di; Zhang, Dan; (16 pag.)CN106243086; (2016); A;,
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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. 137281-39-1, name is 4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid

Weigh 4-[2-(2-amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic acid (60 g 0.2 mol) Add to a 500ml four-neck bottle,Add 200ml of DMF and 60.6g of triethylamine to the temperature to 30 C and stir to dissolve.Benzyl chloride (0.3 mol) was added dropwise, and the mixture was heated to 60 C for 1 hour, and DMF was evaporated to dryness under reduced pressure.Adjust the pH to 6 with dilute hydrochloric acid, stir the crystals, cool down to 0-5 C, filter, and dry the product.4-[2-(2-Benzylamino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic acid (molar yield 96.9%) , purity 99.4%).

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Reference:
Patent; Lunan Pharmaceutical Group Co., Ltd.; Xia Mingjun; Zang Chao; (11 pag.)CN110305137; (2019); A;,
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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. 1445-39-2, name is 2-Amino-5-iodopyrimidine. A new synthetic method of this compound is introduced below., Safety of 2-Amino-5-iodopyrimidine

5-(4-(trifluoromethyl)phenyl)pyrazin-2-amine A 100 mL round bottom flask was charged with 2-amino-5-iodopyrimidine (3.66 g, 21.1 mmol), (4-(trifluoromethyl)phenyl)boronic acid (4.00 g, 21.1 mmol) and MeCN (84 mL). Stirred 15 minutes at room temperature until a nice clear solution is obtained. The resulting solution is then treated with 1,1′-Bis(diphenylphosphino)ferrocene-palladium(11)dichloride dichloromethane complex (508 mg, 695 mumol) was added followed by the sodium carbonate 1M aq. (52.7 mL, 52.7 mmol). Reaction refluxed for 2 hours. Reaction cooled down to room temperature and dissolved with ammonium chloride solution (aq. sat.). Aqueous layer extracted with ethyl acetate (3*). Combined organic layers washed with brine (1*), dried over sodium sulfate, filtered and concentrated to give the crude material. Purification by silica gel flash chromatography (Ethyl Acetate/DCM) provide the title compound as a light yellow solid (4.4 g, 87%). 1H NMR (400 MHz, DMSO-d6) delta 6.76 (s, 2H) 7.76 (d, J=8.41 Hz, 2H) 7.99 (d, J=1.57 Hz, 1H) 8.14 (d, J=8.22 Hz, 2H) 8.62 (d, J=1.37 Hz, 1H). MS (M+1): 240.2.

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, 1445-39-2, 2-Amino-5-iodopyrimidine.

Reference:
Patent; Pfizer Inc.; US2012/165343; (2012); A1;,
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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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Pyrimidine – Wikipedia