Pyrimidines

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. 3435-29-8, name is 4-Amino-6-phenylpyrimidine, the common compound, a new synthetic route is introduced below. Formula: C10H9N3

General procedure: Quinoline-4-carboxylic acid (36.4 mg, 0.226 mmol),3-chloro-5 – (methylthio) benzene amine (50.0 mg, 0.205 mmol) and POCl3 (34.6 mg, 0.226 mmol), pyridine (1 mL) was dissolved in, 80 was stirred for 1 hour dongan. When thin layer chromatography (TLC) check when, a new spot is confirmed, water was added to the reaction mixture, and extracted twice with dichloromethane. And the extracted organic layer was dried using magnesium sulfate, vacuum concentrated and, after the water was removed by filtration of the organic extract over MgSO4 and concentrated by silica gel preparative thin layer chromatography (preparative TLC, ethyl acetate / n- hexane = l / l ) to give to give the title compound (11%) of a white solid.

The synthetic route of 3435-29-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; JUNG, YOUNG SIK; KIM, PIL HO; HAN, SOO BONG; RAGHAVENDRA, ACHARY; KIM, MEE HYEIN; LEE, CHONG KYO; SHIN, JIN SOO; (131 pag.)KR2015/25531; (2015); A;,
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Application of 876343-10-1, 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 876343-10-1, name is 4-Chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Compound 1a-d or 54 (1 mmol) was mixed with the selected amine, 2-25, (3 mmol) and n-butanol (5 ml) and agitated at145 C for 14-24 h. Then the mixture was cooled to 22 C, dilutedwith water (15 ml) and ethyl acetate (40 ml). After phase separation,the water phase was back extracted with more ethyl acetate(2 10 ml). The combined organic phases were washed with brine(10 ml), dried over anhydrous Na2SO4, filtered and concentrated invacuo, before the crude mixture was purified as specified for eachindividual compound

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 876343-10-1, 4-Chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Article; Kaspersen, Svein Jacob; Han, Jin; N°rsett, Kristin G.; Rydsa, Line; Kj°bli, Eli; Bugge, Steffen; Bj°rk°y, Geir; Sundby, Eirik; Hoff, Bard Helge; European Journal of Pharmaceutical Sciences; vol. 59; 1; (2014); p. 69 – 82;,
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Synthetic Route of 5305-59-9, Adding some certain compound to certain chemical reactions, such as: 5305-59-9, name is 6-Chloropyrimidin-4-amine,molecular formula is C4H4ClN3, 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 5305-59-9.

A microwave vial was charged with 4-amino-6-chloropyrimidine (1.0 g, 7.72 mmol), and pyrrolidine (10 mL) was added. The vial was sealed, and heated in the microwave at 180 C for 1 h. After cooling, the reaction was diluted with methanol (30 mL), and silica (15.0 g) was added. All solvents were removed in vacuo, and the remaining silica slurry loaded on a 40.0 g silica column. Elution with a 0% to 10% methanol in dichloromethane gradient yielded 6-(pyrrolidin-1-yl)pyrimidin-4-amine (1.22 g, 96% yield). MS (ESI) calcd for C8H14N4: 164.11

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. 5305-59-9, 6-Chloropyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; CASAUBON, Rebecca, L.; NARAYAN, Radha; OALMANN, Christopher; VU, Chi, B.; WO2013/59587; (2013); A1;,
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Reference of 26452-81-3, 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. 26452-81-3, name is 4-Chloro-6-methoxypyrimidine. A new synthetic method of this compound is introduced below.

A RM of methyl 3-ethoxy-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)thiophene-2-carboxylate (10520 mg, 30 mmol), 4-chloro-6-methoxypyrimidine (4645 mg, 31.5 mmol), dichloro(1 ,1′-bis(diphenylphosphino) ferrocene) palladium (II) dichloromethane adduct) (2449 mg, 3 mmol) and potassium phosphate tribasic monohydrate (20719 mg, 90 mmol) in water (4 mL) and DMF (150 mL) is degassed for 20 min under a nitrogen stream, then stirred at RT for 1 hi 5. The RM is filtered through celite, the filtrate is concentrated under vacuum, the residue is partitioned between water and EtOAc. The organic layer is further washed with brine, dried over MgS04, filtered and concentrated. Purification by FC (heptane/EtOAc, from 1 :0 to 0:1 ) affords the title compound as a yellow solid (7.87 g, 89percent ). LC-MS B: tR = 0.93 min; [M+H]+ = 295.18.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,26452-81-3, its application will become more common.

Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; BOSS, Christoph; CORMINBOEUF, Olivier; FRETZ, Heinz; LYOTHIER, Isabelle; POZZI, Davide; RICHARD-BILDSTEIN, Sylvia; SIENDT, Herve; SIFFERLEN, Thierry; (160 pag.)WO2018/210992; (2018); A1;,
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Reference of 13544-44-0 ,Some common heterocyclic compound, 13544-44-0, molecular formula is C4HCl2IN2, 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.

While being cooled with ice, 3.55 mL of propylamine was added to 83 mL of a tetrahydrofuran solution containing 5.77 g of 2,4-dichloro-5-iodopyrimidine synthesized according to the method described in WO2008/155140A1 and 7.86 mL of N,N-diisopropylethylamine, and the mixture was stirred for 1 hour at room temperature. Then, water and ethyl acetate were added to the reaction mixture. The organic layer was fractionated, and the water layer was extracted using ethyl acetate. The organic layer and the extract were mixed together, washed sequentially with a 1.0 mol/L aqueous hydrochloric acid solution, water, a saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure, thereby obtaining 6.44 g of 2-chloro-5-iodo-N-propylpyrimidin-4-amine in the form of oil. MS m/z(M+H): 298.3

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13544-44-0, its application will become more common.

Reference:
Patent; FUJIFILM Corporation; NAGATO, Yusuke; MIZUMOTO, Shinsuke; MURAKAMI, Tatsuya; TANAKA, Tomoyuki; (25 pag.)US2018/127382; (2018); A1;,
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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;,
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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.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;,
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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;,
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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;,
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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. 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;,
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