Tag: M.W:200-300

Reference of 7627-39-6, 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. 7627-39-6, name is 2,4-Dichloro-5-(ethoxymethyl)pyrimidine. A new synthetic method of this compound is introduced below.

[0133] To a stirred solution of 3-hydroxy-10-(methyl-d3)-9,10,11,12-tetrahydro-8H- [1,4]diazepino[5′,6′:4,5]thieno[3,2-f]quinolin-8-one-10,11,11-d3 (INT-1) (200.0 mg, 0.6 mmol) in DMSO (4 mL) was added K2CO3 (180.8 mg, 1.3 mmol) and stirred at room temperature for 40 mins followed by addition of 2,4-dichloro-5-(ethoxymethyl)pyrimidine (203.4 mg, 1.0 mmol). This reaction mixture was stirred at room temperature overnight. LCMS showed the reaction was complete. The reaction mixture was passed though silica gel and purified by reverse phase prep-HPLC to afford 3-((2-chloro-5-(ethoxymethyl)pyrimidin-4-yl)oxy)-10-(methyl-d3)- 9,10,11,12-tetrahydro-8H-[1,4]diazepino[5′,6′:4,5]thieno[3,2-f]quinolin-8-one-10,11,11-d3 (I-2) (111.1 mg, 39.0%) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) delta 9.36 (d, J = 9.0 Hz, 1H), 8.71 (s, 1H), 8.19 (s, J = 9.0 Hz, 1H), 8.12 (s, 1H), 7.86 (d, J = 9.0 Hz, 1H), 7.63 (d, J = 9.0 Hz, 1H), 4.66 (s, 1H), 3.62 (dd, J = 4.0 Hz, 2H), 1.20 (t, J = 4.0 Hz, 3H). MS m/z (M+H): 476.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7627-39-6, its application will become more common.

Reference:
Patent; CELGENE CAR LLC; MALONA, John; SURAPANENI, Sekhar S.; (116 pag.)WO2018/170201; (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. 113583-35-0, name is 2-Methanesulfonyl-4,6-dimethoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

Reference Example 7 A solution of 2,2-dimethyl-5-hydroxy-4-oxo-benzo-1,3-dioxin (8.0 g) in tetrahydrofuran was added dropwise during 0.25 hour to a stirred suspension of sodium hydride (1.75 g of 60%) under nitrogen. After 0.25 hour 4,6-dimethoxy-2-methylsulphonylpyrimidine (9.68 g) was added during 5 minutes and the mixture heated at reflux overnight. The cooled mixture was diluted with water, extracted (ether), dried (magnesium sulphate), evaporated and purified by chromatography on silica gel eluding with isohexane/ethyl acetate to give 5-(4,6-dimethoxypyrimidin-2-yl)oxy-2,2-dimethyl-4-oxo-benzo-1,3-dioxin (2.64 g).

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, 113583-35-0, 2-Methanesulfonyl-4,6-dimethoxypyrimidine.

Reference:
Patent; Cramp, Michael Colin; Mack, Stephen Robert; Gingell, Michael; US2001/29239; (2001); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 39876-88-5, Adding some certain compound to certain chemical reactions, such as: 39876-88-5, name is 4-Chlorobenzofuro[3,2-d]pyrimidine,molecular formula is C10H5ClN2O, 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 39876-88-5.

4-Chlorobenzofuro[3,2-djpyrimidine (500 mg, 2.44 mmol), 6-methyl-2-vinyl-1,3 ,6,2-dioxazaborocane-4,8-dione (492 mg, 2.69 mmol), chloro(2-dicyclohexylphosphino-2?,6?-dimethoxy- 1,1 ?-biphenyl) [2-(2?-amino- 1,1?-biphenyl)jpalladium(II) (176 mg, 0.244 mmol), potassium phosphate tribasic (3.89 g, 18.3 mmol) were combined under N2 (g). 1,4-Dioxane (20 ml) and water (4.0 ml) was added under N2 (g). The reaction was stirred at 80 C for 1 hr. The reaction was concentrated, adsorbed onto celite and was purified on silica gel (Biotage,EtOAc/hexanes gradient, 0-100% over 10 CVs) to give the expected product 4- vinylbenzofuro[3,2-djpyrimidine (254 mg, 1.30 mmol, 53.0 % yield) LCMS (M+H) =196.80.

According to the analysis of related databases, 39876-88-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BELEMA, Makonen; BOWSHER, Michael S.; DESKUS, Jeffrey A; EASTMAN, Kyle J.; GILLIS, Eric P; FRENNESSON, David B; IWUAGWU, Christiana; KADOW, John F.; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PEESE, Kevin M; SAULNIER, Mark G; SIVAPRAKASAM, Prasanna; (463 pag.)WO2018/127800; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 90914-41-3, 3-Bromo-4-chloro-1H-pyrazolo[3,4-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, Quality Control of 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine, blongs to pyrimidines compound. Quality Control of 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine

a) 3-bromo-4-chloro-1-(phenylsulfon -1 H-pyrazolo[3,4-c ]pyrimidineTo a dry 500 mL flask was added 3-bromo-4-chloro-1 H-pyrazolo[3,4-d]pyrimidine (4 g, 17.13 mmol) in THF (160 mL). DMF (10 mL) was added and the stirred contents were cooled to 0 C. NaH (60% dispersion in oil, 0.82 g, 20 mmol) was added portionwise and the mixture was stirred for 15 min. Benzene sulfonyl chloride (2.4 mL, 18.8 mmol) was added dropwise via syringe. After stirring for 15 min, the reaction vessel was removed from an ice bath. After 2 h, the contents were poured onto ice-water (50 mL), and stirred for 30 min. The white precipitate was filtered and washed with water to afford 4.38 g of a white solid. The mother liquor was concentrated down, extracted thrice with EtOAc and evaporated to dryness. The residue was triturated with EtOAc to afford an additional 1.3 g of the title compound. A total weight of 5.68 g of title compound was obtained (89%). LCMS(ES) m/e 373, 375 (M, M+2); 1H NMR (400 MHz, DMSO-d6) delta ppm 9.1 1 (s, 1 H), 8.1 1 (dd, J = 1.14, 8.46 Hz, 2H), 7.84 (s, 1 H), 7.71 (d, J = 8.34 Hz, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,90914-41-3, 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE LLC; HAMMOND, Marlys; KALLANDER, Lara, S.; LAWHORN, Brian, Griffin; PHILP, Joanne; SARPONG, Martha, A.; SEEFELD, Mark, Andrew; WO2011/149827; (2011); 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. 16097-63-5, name is 4-Chloro-2-(methylsulfanyl)-6-(trifluoromethyl)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C6H4ClF3N2S

Step 3: 274-02 (38 mg, 0.16 mmol) , 49-01 (30 mg, 0.13 mmol) and K2CO3 (28 mg, 0.2 mmol) was mixed together in dry DMF (2 mL) in a microwave tube, the reaction was microwaved at 90 for 2 hrs. cooled to r. t. water was added, and the organic layer was extracted with ethyl acetate for three times, the organic layer was combined, dried and further purified by flash column chromatography (EA/PE 1/8) to give 54 mg of 274-03 as a colorless oil, yield: 96. Mass (m/z) : 430.15, [M+H] +.

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, 16097-63-5, 4-Chloro-2-(methylsulfanyl)-6-(trifluoromethyl)pyrimidine.

Reference:
Patent; NATIONAL INSTITUTE OF BIOLOGICAL SCIENCES, BEIJING; ZHANG, Zhiyuan; WANG, Xiaodong; HUANG, Shaoqiang; JIANG, Xian; LI, Li; ZHANG, Zhaolan; HAN, Jianguang; (189 pag.)WO2018/14802; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 137281-39-1, 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 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.

4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic acid (64.6 g 0.19 mol)Add 1L four-necked bottle, add 650ml DMF and stir to dissolve.The temperature was raised to 50 C, 0.38 mol of N, carbonyl diimidazole was added, and the reaction was kept at 60 C for 2 hours, and L-glutamic acid diethyl ester (0.38 mol) was added thereto, and the mixture was heated to 80 C for 3 hours, and evaporated to dryness under reduced pressure.After adding 800 ml of dichloromethane to dissolve, pour into a mixed solution of 1600 ml of pure water and 160 ml of triethylamine, and stir to separate the liquid.The organic phase was separated, washed twice with pure water 1600 ml×2, dried and evaporated to dryness, and stirred and dissolved by adding 500 ml of absolute ethanol.72 g of p-toluenesulfonic acid monohydrate and 200 ml of absolute ethanol solution were added dropwise under reflux, and the reaction was refluxed for 1 hour.The crystal was cooled, filtered, and dried to obtain 87.2 g of a crude product (molar yield 70.1%, purity 92.3%, impurity VI content 6.52%). 87.2 g of the above crude product was added to a three-neck reaction flask, and 350 ml of N,N-dimethylformamide was added.Heat to 40-45 C to stir and dissolve. After total dissolution, add 700 ml of absolute ethanol.The solid was gradually precipitated, and the temperature was lowered to room temperature, and the mixture was stirred and crystallized for 1-2 h, and filtered to give a solid, 69.8 g, yield: 80.0%.The above purification operation was repeated once to obtain 55.4 g of a solid (purity: 98.2%, impurity VI content: 0.07%).

According to the analysis of related databases, 137281-39-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Lunan Pharmaceutical Group Co., Ltd.; Xia Mingjun; Zang Chao; (11 pag.)CN110305137; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 1044767-99-8, 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. 1044767-99-8, name is 5-Bromo-4-chloropyrimidin-2-amine. A new synthetic method of this compound is introduced below.

To a mixture of 5-bromo-4-chloropyrimidin-2-amine (1.0 g, 4.80 mmol) and trans-4- aminocyclohexanol (608 mg, 5.28 mmol) in DMA (20 mL) was added ZV-ethyl-ZV- isopropylpropan -2-amine (744 mg, 5.76 mmol) and K2CO3 (1.33 g, 9.60 mmol). The reaction mixture was stirred at 160 C for 4 h and then concentrated under reduced pressure. The residue was purified by column chromatography with pre-packed silica gel disposable column to provide the desired product /ra//.s-4-((2-amino-5-bromopyrimidin-4- yl)amino)cyclohexanol (1.0 g, 73%) as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1044767-99-8, 5-Bromo-4-chloropyrimidin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; WANG, Xiaodong; ZHAO, Jichen; FRYE, Stephen; (146 pag.)WO2019/222538; (2019); 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

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

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