Day: September 13, 2021

Synthetic Route of 923595-58-8, 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 923595-58-8, name is 5-Chloro-3-iodopyrazolo[1,5-a]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of (R)-3-iluotO-2-(pyrrolidin-2-yl)pyridine (1 163 mg, 4.302 mmol) and 5-chloro-3-iodopyrazolo[l,5-a]pyrimidine (1.76 g, 6.298 mmol) in DMF (15 mL) was DIPEA (4.9 mL, 27.99 mmol). The mixture was stirred at 110 C for 1 hour and then cooled to rt overnight. The mixture was extracted with AcOEt, dried and concentrated. The product was purified by column chromatography using 0-100% acetone in hexane. Product was isolated as an orange oil (1.42 g, 50%).

According to the analysis of related databases, 923595-58-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PYRAMID BIOSCIENCES, INC.; PAL, Kollol; CIBLAT, Stephane; ALBERT, Vincent; BRUNEAU-LATOUR, Nicolas; BOUDREAULT, Jonathan; (139 pag.)WO2019/118584; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.696-07-1, name is 5-Iodouracil, molecular formula is C4H3IN2O2, molecular weight is 237.9833, as common compound, the synthetic route is as follows.Safety of 5-Iodouracil

To a dry DMF (50 mL) solution of 5-iodouracil 23 (5.00 g, 21 mmol), tetrakis (triphenylphosphine) palladium (0) (1.00 g, 0.87 mmol, 0.04 equiv. ) and copper iodide (0.80 g, 4.2 mmol, 0.2 equiv. ) under a nitrogen atmosphere was added dry DIPEA (7.3 mL, 5.42 g, 42 mmol, 2 equiv. ) and 1-DODECYNE 24 (13.5 ML, 10.48 g, 63 mmol, 3 equiv. ) via syringe with stirring. The initially opaque yellow solution proceeded to change colour on stirring at room temperature to a clear dark yellow solution, and eventually an opaque dark green suspension formed after a couple of hours. The suspension was allowed to react at RT with stirring for 18 h. TLC analysis of the resulting mixture indicated that most of the starting material had reacted, and the presence of a blue fluorescent spot was clearly observed. Dry triethylamine (25 mL) and a further addition of copper iodide (0.80 g) was then made to the suspension, and the resultant reaction mixture heated to 80 C for 6 h with stirring under N2. The suspension was allowed to cool to RT overnight with stirring. The resultant precipitate was collected by suction filtration, and washed consecutively with methanol and DCM. The collected solid was triturated in hot methanol to yield the title COMPOUND 26 as a white insoluble solid of weight 3.79 g (65 % from 23).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,696-07-1, 5-Iodouracil, and friends who are interested can also refer to it.

Reference:
Patent; UNIVERSITY COLLEGE CARDIFF CONSULTANTS LIMITED; REGA FOUNDATION; WO2004/96813; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 3680-69-1, 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 3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (8 g, 52.3 mmol) in CH2Cl2 (200 ml) was added NIS (14 g, 62.5 ml). The mixture was stirred at rt for 5 h. LC- MS indicated complete reaction. The mixture was filtered and the filtered solid was washed with CH2Cl2 (50 ml), followed by hot water (500 ml). The solid was then dried in vacuum oven at 40 C for 2 days to give 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine, MM as a gray solid (13.6 g, 93%). 1H NMR (DMSO-d6) delta 12.97 (br s, 1H), 8.60 (s, 1H), 7.95 (s, 1H). LC/MS m/z 279.9 (M+H).

According to the analysis of related databases, 3680-69-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHIMERIX, INC.; ALMOND, Merrick; LANIER, Ernest, Randall; MUSSO, David, Lee; WARE, Roy; WO2010/135520; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 10244-24-3 ,Some common heterocyclic compound, 10244-24-3, molecular formula is C12H17ClN4O2, 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.

4,4 ‘ – (6-chloro-pyrimidine -2,4-diyl) two morpholine (210 mg, 0 . 74mmol), 3 – (2-amino-5-bromo-(trifluoromethyl) pyridin-3-yl) acrylic acid methyl ester (480 mg, 1 . 47mmol),were taken and then palladium acetate (34 mg, 0 . 15mmol), n-butyl, di (1-adamantyl) diphenylphosphinobiphenyl (80 mg, 0 . 22mmol), pinacone esterjoint boric acid (470 mg, 1 . 9mmol) and cesium carbonate (842 mg, 2 . 6mmol) were added to the toluene (10 ml) and methanol (10 ml) under the protection of nitrogen and the temperature was raised to 75 C reaction for 16 hours. adding water (50 ml), dichloromethane (100 ml) extraction, the organic phase with saturated salt water (60 ml) washing, drying by anhydrous sodium sulfate, concentrated, crude product by silica gel column chromatography (dichloromethane: methanol =20:1) purified title compound (320 mg, yield 87.6%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10244-24-3, its application will become more common.

Reference:
Patent; Shandong Xuan Bamboo Pharmaceutical Technology Co., Ltd.; Wu, Yong qian; (49 pag.)CN105461714; (2016); A;,
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. 871254-61-4, name is 2,4-Dichloropyrimidine-5-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 871254-61-4

To a solution of 2,4-dichloropyrimidine-5-carbaldehyde (20.2 g, 114 mmol) in THF (530 mL) at 0 C was added a chilled solution of hydrazine hydrate (11.5 g, 2 eq) in THF (230 mL) over 5 minutes. The reaction mixture was stirred 10 minutes at 0 C and 1 hour at room temperature. It was then diluted with EtOAc and H20 and the layers were separated. The aqueous layer was extracted with EtOAc then the combined organic phase was dried over Na2S04, filtered, and concentrated. The crude product was purified by normal-phase column chromatography on silica gel (50% EtO Ac/hexanes) to afford 6-chloro-lH- pyrazolo[3,4-d]pyrimidine as a light-yellow solid (8.8 g, 50% yield). 1HNMR (400 MHz, CD3OD) d (ppm): 9.17 (s, 1H), 8.30 (s, 1H).

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, 871254-61-4, 2,4-Dichloropyrimidine-5-carbaldehyde.

Reference:
Patent; RAPT THERAPEUTICS, INC.; BUI, Minna, H.T.; DUKES, Adrian, O.; HAN, Xinping; HU, Dennis, X.; JACKSON, Jeffrey, J.; KO, Yoo, Min; LEGER, Paul, R.; MA, Anqi; MAUNG, Jack; NG, Andrew, A.; OKANO, Akinori; ROBLES, Omar; SHIBUYA, Grant; SHUNATONA, Hunter, P.; SCHWARZ, Jacob, B.; SHAKHMIN, Anton, A.; WUSTROW, David, J.; ZIBINSKY, Mikhail; (0 pag.)WO2019/236631; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 62802-42-0, 2-Chloro-5-fluoropyrimidine, 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, 62802-42-0, blongs to pyrimidines compound. Product Details of 62802-42-0

To a 5- (0934) L autoclave was added 2-chloro-5-fluoropyrimidine (150.0 g, 1132 mmol), potassium- (E)-propenyl trifluoroborate (251.0 g, 1698 mmol), potassium carbonate (235.0 g, 1698 mmol), 1,4-dioxane (1.5 L, 10.0 mL/g), and water (300.0 mL, 2.0 mL/g) at RT. The reaction mixture was degassed with nitrogen for 15 minutes. PdCi2(dppf) (16.56 g, 22.64 mmol,) was added, and the resulting reaction mixture was again degassed with nitrogen for 5 minutes and then heated to 70 C for 16 h. The reaction mass was cooled to RT and filtered through a pad of Celite brand filter aid. The Celite brand filter aid pad was washed with diethyl ether (1.0 L). The filtrate was partitioned between diethyl ether (8.0 L) and water (6.0 L). The organic layer was washed with brine (2.5 L) and dried over sodium sulfate, filtered and concentrated in vacuo (bath temperature; 30 – 35 C) to obtain the initial material which was purified by column chromatography (silica gel 60-120 mesh, mobile phase: 0-5% EtOAc in hexane) to give Example 138.11 (140.0 g, 1013 mmol, 90% yield) as a yellow oil. NMR (400 MHz, DMSO-Patent; AMGEN INC.; DRANSFIELD, Paul John; HARVEY, James S.; MA, Zhihua; SHARMA, Ankit; (281 pag.)WO2019/89335; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 5750-76-5, 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. 5750-76-5, name is 2,4,5-Trichloropyrimidine, molecular formula is C4HCl3N2, 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.

Id) 2-Amino-N-methyl-benzamide (1.5g, 10 mmol) and 2,4,5-Trichloro-pyrimidine (1.31 ew) were combined in DMF (30 mL). Potassium carbonate (1.3 eq) was added the mixture heated to 750C for 4.5 h and stirred at room temperature overnight. The mixture was poured into water and the white precipitate that ensued was filtered and dried to give 2- (2,5-dichloro-pyrimidin-4-ylamino)-N-methyl-benzamide (2.7 g, 92%): 1H NMR (400 MHz, DMSOd6) I’ 12.19 (s, IH), 8.86 (s, IH), 8.54 – 8.48 (m, 2H), 7.81 (d, J =7.9 Hz, IH), 7.61 (t, J = 8.7 Hz, I H), 7.23 (t, J = 8.9 Hz, IH), 2.50 (d, J = 1.5 Hz, 3H).

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 5750-76-5, 2,4,5-Trichloropyrimidine.

Reference:
Patent; CEPHALON, INC.; PHARMACOPEIA DRUG DISCOVERY, INC.; WO2008/51547; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 956034-07-4, 2,4-Dichlorofuro[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, 956034-07-4, blongs to pyrimidines compound. Quality Control of 2,4-Dichlorofuro[3,2-d]pyrimidine

[0174] To a reaction flask were added compound 31-c (0.088 mmol), compound 31-b (according to the synthesisprocedure in the patent: WO 2011/079230 A2) (15 mg, 0.080 mmol), PdCl2(dppf) (3 mg, 0.004 mmol), 2 N aqueoussodium carbonate solution (0.12 mL, 0.24 mmol) and 1,4-dioxane (3 mL). Under nitrogen, the mixture was stirredovernight at 80C. After the reaction mixture was concentrated, the residue was diluted with water (15 mL), and theaqueous phase was extracted with dichloromethane (15 mL 3 2). The organic layers were combined and washedsuccessively with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to givecrude product 31-a (35 mg) which was used directly in the next reaction without further purification. LC-MS (ESI): m/z=248.1 [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,956034-07-4, its application will become more common.

Reference:
Patent; Shanghai Yingli Science and Technology Co., Ltd; Shanghai Chemexplorer Co., Ltd.; XU, Zusheng; EP2860181; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1749-68-4, 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.1749-68-4, name is 6-Chloro-2-methylpyrimidin-4-amine, molecular formula is C5H6ClN3, molecular weight is 143.57, as common compound, the synthetic route is as follows.

Example 20 2-({ [5-methyl-2-(2-methylbiphenyl-3-yl)[l,2,4]triazolo[l,5-c]pyrimidin-7- yl] methyl } am ino )ethanol Step 1 : 7-chloro-5-methyl[ 1, 2, 4 Jtriazolof 1, 5-c Jpyrimidin-2-amine To a solution of 6-chloro-2-methylpyrimidin-4-amine (AK Scientific, cat W3822: 585 mg, 4.07 mmol) in 1,4-dioxane (20.4 mL) was added ethoxycarbonyl isothiocyanate (553 mu, 4.89 mmol). The reaction mixture was heated at 50 C for 6 h then cooled to room temperature and concentrated. The residue was dissolved in methanol (15 mL)/ethanol (15 mL) then N,N-diisopropylethylamine (1.42 mL, 8.15 mmol) was added, followed by hydroxylamine hydrochloride (849 mg, 12.2 mmol). The mixture was stirred at 50 C for 3 h then cooled to room temperature and concentrated. The residue was directly used for the next step without further purification. LC-MS calculated for CeHvClNs (M+H)+: m/z = 184.0; found 184.0.

Statistics shows that 1749-68-4 is playing an increasingly important role. we look forward to future research findings about 6-Chloro-2-methylpyrimidin-4-amine.

Reference:
Patent; INCYTE CORPORATION; WU, Liangxing; SHEN, Bo; LI, Jingwei; LI, Zhenwu; LIU, Kai; ZHANG, Fenglei; YAO, Wenqing; (120 pag.)WO2017/70089; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 2380-63-4, 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. 2380-63-4, name is 1H-Pyrazolo[3,4-d]pyrimidin-4-amine. A new synthetic method of this compound is introduced below.

500 mg 1H-pyrazole [3,4-d]pyrimidine-4-amine and 1.25 g of N-iodosuccinimide were dissolved in 5 ml of N,N-dimethylformamide, under argon, the mixture was heated to 80 C for 18 hours, and after cooled to room temperature, it was poured into 20 ml of saturated aqueous solution of sodium thiosulfate and then beated and filtered. The cake was dried to give 1.2 g of brown solid. 1H NMR (300 MHz, DMSO-d6) delta 13.81 (s, 1H), 8.13 (s, 1H), 8.17 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2380-63-4, 1H-Pyrazolo[3,4-d]pyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; Shanghai Institute of Materia Medica, Chinese Academy of Sciences; DUAN, Wenhu; GENG, Meiyu; WANG, Yuming; AI, Jing; FAN, Jun; DAI, Yang; DING, Jian; (133 pag.)EP3486244; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia