Month: March 2022

Reference of 55405-67-9, 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. 55405-67-9, name is 3-Bromopyrazolo[1,5-a]pyrimidine, molecular formula is C6H4BrN3, 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.

General procedure: To a solution of 6-bromopyridine-2-carbonitrile (80 mg, 0.44 mmol) and 4-(morpholin-4-yl)-5-(4,4, 5, 5-tetramethyl- 1, 3,2-d ioxaborolan-2-yl )-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (P2) (241 mg, 0.523 mmol) in1,4-dioxane (2.5 mL) and water (0.5 mL) was addedtetrakis(triphenylphosphine)palladium(0) (51 mg, 44 pmol) and sodium carbonate (140 mg, 1.32 mmol). The reaction mixture was heated at 120 C under microwave irradiation for 15 minutes, then diluted with water (30 mL) and extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution (100 mL), dried over sodium sulfate, filtered, and concentratedin vacuo; purification via preparative thin layer chromatography (Eluent: 1:1 petroleum ether ethyl acetate) afforded the product as a brown oil. Yield: 110 mg, 0.252 mmol, 57%. 1H NMR (400 MHz, CDCl3) 8.52 (s, 1H), 7.84-7.93 (m, 2H), 7.74 (s, 1H), 7.59 (dd, J=7.0, 1.2 Hz, 1H), 5.66 (s, 2H), 3.56-3.65 (m, 6H), 3.34-3.40 (m, 4H), 0.93 (dd, J8.3, 8.0 Hz, 2H), -0.05 (s, 9H).

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 55405-67-9, 3-Bromopyrazolo[1,5-a]pyrimidine.

Reference:
Patent; PFIZER INC.; GALATSIS, Paul; HAYWARD, Matthew Merrill; HENDERSON, Jaclyn; KORMOS, Bethany Lyn; KURUMBAIL, Ravi G; STEPAN, Antonia Friederike; VERHOEST, Patrick Robert; WAGER, Travis T.; ZHANG, Lei; WO2014/1973; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 31737-09-4, 6-Chloro-1-methylpyrimidine-2,4(1H,3H)-dione, 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, Product Details of 31737-09-4, blongs to pyrimidines compound. Product Details of 31737-09-4

To a stirred solution of 6-chloro-1-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione (3 g, 18.68 mmol, 1 equiv.) and tert-butyl piperazine-1-carboxylate (4.2 g, 22.42 mmol, 1.2 equiv.) in EtOH (60 mL) was added NaHCO3(3.1 g, 37.37 mmol, 2 equiv.) at room temperature. The mixture was stirred at 70 degrees Celsius for 5 h. The mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with CH2Cl2/ MeOH (15:1 to 10:1) to afford tert-butyl 4-(3-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4- yl)piperazine-1-carboxylate(5.38 g, 92.78%) as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,31737-09-4, 6-Chloro-1-methylpyrimidine-2,4(1H,3H)-dione, and friends who are interested can also refer to it.

Reference:
Patent; GOLDFINCH BIO, INC.; YU, Maolin; DANIELS, Matthew, H.; HARMANGE, Jean-christophe, P.; TIBBITTS, Thomas, T.; LEDEBOER, Mark, W.; WALSH, Liron; MUNDEL, Peter, H.; MALOJCIC, Goran; (860 pag.)WO2019/55966; (2019); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 67383-32-8, 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. 67383-32-8, name is Ethyl 4-hydroxy-2-methylpyrimidine-5-carboxylate. A new synthetic method of this compound is introduced below.

Step 2A 5-Ethoxycarbonyl-2-methyl-3-(2-oxo-3,3-dimethyl-butyl)pyrimid-4-one To a suspension of 5-ethoxycarbonyl-2-methylpyrimid-4-one (2.7 g, 14.75 mmol.) in DME (20 ml), tetrabutylammonium fluoride (22 ml, 22.0 mmol.) was added. The solution was stirred at room temperature until solids dissolved, then 1-bromopinacolone (2.2 ml, 1.1 eq., 16.22 mmol) was added. The solution was stirred overnight and concentrated to a brown oil. The crude mixture was purified by silica gel column chromatography (hexane/ethyl acetate, 100/0 to 0/100). A less polar O-alkylated by-product was eluted first (1.8 g) and then the desired N-alkylated product (1.1 g); MS (281, M+H)+. NMR (CDCl3, delta): 8.57 (1H, s), 5.06(1H, s), 4.35(2H, q), 2.42 (3H, s), 1.34 (3H, t), 1.30 (9H,s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,67383-32-8, its application will become more common.

Reference:
Patent; Neurocrine Biosciences, Inc.; US6537998; (2003); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 19752-61-5, 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 19752-61-5, name is 5-Bromo-2,4-di-tert-butoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

The starting material 2,4-di-tert.butoxy-5-(3′-furyl)pyrimidine was prepared as follows: A 250 ml flask equipped with condenser, magnetic stirrer and nitrogen inlet was charged with 7.3 g (0.024 mole) of 5-bromo-2,4-di-tert-butoxypyrimidine, 0.75 mmol of tetrakis(triphenylphosphine)palladium (0) and 80 ml of 1,2-dimethoxyethane. After stirring for 10 min 3.0 g (0.027 mole) of 3-furanboronic acid was added, immediately followed by 60 ml of 1M sodium carbonate solution. The reaction mixture was refluxed for 4 hours with vigorous stirring under nitrogen. After cooling to room temperature, the traces of catalyst were filtered off, the organic solvent was evaporated under reduced pressure and the residue diluted with water and extracted with three 50 ml portions of ether. The combined etheral phases were washed with water, saturated sodium chloride solution and dried over magnesium sulphate. The ether was evaporated and the residue was purified by flash chromatography using hexane-ethyl acetate (4:1) as eluent, yielding 4.1 g (59%) of the title compound as an oil. Anal. Found C 66.5, H 7.68, N 9.64, O 17.0. Calc. for C16 H22 N2 O3 (290.4) C 66.2, H 7.64, N 9.65, O 16.5.

According to the analysis of related databases, 19752-61-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Medivir AB; US5440040; (1995); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 695-87-4, 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. 695-87-4, name is 5-Methoxypyrimidin-4(1H)-one, molecular formula is C5H6N2O2, 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.

A suspension of 1.9 g (0.015 mol) of 5-methoxy-3H-pyrimidin-4-one (Example P2) in 4.2 ml (0.046 mol) of phosphorus oxychloride and 5.0 mi (0.031 mol) of N, N-diethylaniline is heated at 115C for 3 hours. The dark, homogeneous mixture obtained is hydrolyse by adding crushed ice, the temperature being kept below 30C. Extraction with diethyl ether, drying of the combined organic ethereal phases over sodium sulfate, and purification on a silica gel column (eluant : ethyl acetate/n-hexane 1/9) yields the desired target compound in a yield of 1.3 g (58 % of theory). Further purification by means of sublimation at 80-85C/15 Torr yields the desired title compound, having a melting point of 63-64C. oh NMR (300 MHz, Ceci3) : 8.635 ppm (s, 1H) ; 8.321 ppm (s, 1H) ; 4.025 ppm (s, 3H).

According to the analysis of related databases, 695-87-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WO2003/87067; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 1192064-63-3, name is 2,5-Dichloro-4-methylpyrimidine, molecular formula is C5H4Cl2N2, 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. Computed Properties of C5H4Cl2N2

N-butyllithium (1.6 M in hexanes, 4.99 mL) is added drop wise to diisopropylamine (1.13 mL) in tetrahydrofuran (20 mL) at -50 to -60 C. under an argon atmosphere. The mixture is stirred for 30 min at this temperature, cooled to -70 C., and 2,5-dichloro-4-methyl-pyrimidine (1.00 g) is added. After 1 h a solution of 4-formyl-piperidine-1-carboxylic acid tert-butyl ester (1.37 g) in tetrahydrofuran (10 mL) is added and the resulting mixture is stirred for another hour. The reaction is quenched with acetic acid solution (1% in ethanol, 10 mL) and the mixture is diluted with ethyl acetate. The organic phase is separated, washed with water and aqueous NaHCO3 solution, dried over MgSO4, and concentrated in vacuo. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 75:25?30:70) to give the title compound. LC (method 7): tR=1.40 min; Mass spectrum (ESI+): m/z=376 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 1192064-63-3.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/322784; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
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. 60186-89-2, name is 4-Bromo-2,6-dimethoxypyrimidine. A new synthetic method of this compound is introduced below., Safety of 4-Bromo-2,6-dimethoxypyrimidine

To a solution of 4-bromo-2,6-dimethoxy-pyrimidine (6.80 g, 27.94 mmol) in THF (190 mL) and diethylether (190 mL) n-butyllithium (in hexane/THF, 2.01 g, 30.74 mmol) is added dropwise with stirring at -78 C. After 4 min ethyl trifluoroacetate (4.46 g, 30.74 mmol) in THF (50 mL) is added dropwise at -78 C. The reaction mixture is stirred for 30 min at -78 C and then the reaction is allowed to warm to room temperature slowly and stirred over night at room temperature. To the reaction mixture 1 N HCI solution is added . The resulting mixture is extracted with EA and washed with sat. sodium chloride solution and water. The organic phase is dried over sodium sulfate, filtered and the solvent is evaporated in vacuo. The residue is purified by flash col umn chromatography (silica gel, PE / EA = 8 12) to give the product. MS (ESI+): m/z = 255 [M+H]+ TLC (silica gel, PE/EA 3/1 ): Rf = 0.20

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, 60186-89-2, 4-Bromo-2,6-dimethoxypyrimidine.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; EICKMEIER, Christian; GERLACH, Kai; HEINE, Niklas; WEBER, Alexander; GROSS, Ulrike; WO2014/127816; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 34253-03-7 ,Some common heterocyclic compound, 34253-03-7, molecular formula is C6H6N2O2, 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.

To a solution of methyl pyrimidine-2-carboxylate (25 g, 181 mmol, 1 equiv) in MeOH (500 mL) was added NaBHt (8.2 g, 217 mmol, 1.2 equiv) at 0C. The reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was quenched with H2O (20 mL), concentrated in vacuo and the residue was purified by flash column chromatography (eluted with PE/EtOAc = 1/1) to afford the title compound pyrimidin-2- ylmethanol as a yellow oil (16 g, 80% yield). LC-MS : m/z 111.0 (M+H)+

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. 34253-03-7, Methyl pyrimidine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ANNAPURNA BIO INC.; TANG, Haifeng; BOYCE, Sarah; HANSON, Michael; NIE, Zhe; (213 pag.)WO2019/169193; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 33630-25-0, 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. 33630-25-0, name is 2-Phenylpyrimidin-4-amine. A new synthetic method of this compound is introduced below.

General procedure: A solution of acyl azide 10 (0.640 g, 2.14 mmol) in anhydrous toluene (30 mL) was heated at 100 °C for 45 min. After cooling, the solution was divided equally between three sealed tubes and anilines 13, 14 and 15 (1.42 mmol, 2 equiv) added to the appropriate sealed tube. The tubes were re-capped and heated to 100 °C for a further 2 h. After cooling the toluene was evaporated and the residue purified by flash column chromatography (1:1 hexane/EtOAc to neat EtOAc gradient containing 2.5percent by volume Et3N) to furnish the ureas 17, 18 and 19.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,33630-25-0, 2-Phenylpyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Article; Djung, Jane F.; Mears, Richard. J.; Montalbetti, Christian A.G.N.; Coulter, Thomas S.; Golebiowski, Adam; Carr, Andrew N.; Barker, Oliver; Greis, Kenneth D.; Zhou, Songtao; Dolan, Elizabeth; Davis, Gregory F.; Bioorganic and Medicinal Chemistry; vol. 19; 8; (2011); p. 2742 – 2750;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1250967-81-7, 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.1250967-81-7, name is 2-Chloro-4-isopropoxypyrimidine, molecular formula is C7H9ClN2O, molecular weight is 172.61, as common compound, the synthetic route is as follows.

To a 0C solution of Intermediate 1E (10 mg, 0.026 mmol) and 2-chloro-4- isopropoxy- pyrimidine (7 mg, 0.04 mmol) in DMF (0.3 mL) was added NaH (2 mg of a 60% dispersion in mineral oil, 0.05 mmol). The reaction mixture was stirred at RT for 1 h. LCMS indicated the formation of the two products. Water (0.4 mL) and MeOH (0.4 mL) were added to the reaction mixture, which was stirred for another 1 h at RT, then was concentrated in vacuo. The residue was diluted with H20 (1 mL) and the pH was adjusted with 1N aq. HC1 to ~5, then was extracted with EtOAc (3 x 2 mL). The combined organic extracts were washed with brine (2 mL), dried (MgS04) and concentrated in vacuo. The crude product was purified by preparative LC/MS (Column: XBridge Cl 8, 19 x 200 mm, 5-pm particles; Mobile Phase A: 5:95 MeCN:H20 with 0.1% TFA; Mobile Phase B: 95:5 MeCN:H20 with 0.1% TFA; Gradient: 15-55% B over 27 min, then a 3-min hold at 100% B; Flow: 20 mL/min). Fractions containing the desired product were combined and dried via centrifugal evaporation. The first eluting isomer was further purified by preparative LC/MS (Column: XBridge Shield RP18, 19 x 200 mm, 5-pm particles; Mobile Phase A: 5:95 MeCN:H20 with l0-mM aq. NH4OAc; Mobile Phase B: 95:5 MeCN:H20 with lO-mM aq. NH4OAc; Gradient: 21-46% B over 25 min, then a 2-min hold at 46% B; Flow: 20 mL/min) to give Example 249 (1.8 mg, 15% yield). Its estimated purity by LCMS analysis was 100%. LCMS, [M + H]+ = 483.4. NMR (500 MHz, DMSO-^e) d 8.28 (d, = 5.6 Hz, 1H), 7.84 (s, 1H), 7.51 (s, 1H), 6.53 (d, J= 5.6 Hz, 1H), 6.02 (s, 2H), 5.09 (p, J= 6.2 Hz, 1H), 4.72 (s, 1H), 4.11 (s, 3H), 2.26 (s, 3H), 1.96 – 1.41 (m, 8H), 1.25 (d, J= 6.2 Hz, 6H; the proton a to the carboxylic acid is not observed due to water suppression). hLPAi IC50 = 67 nM. The second eluting isomer was further purified by preparative LC/MS (Column: XBridge C18, 19 x 200 mm, 5-pm particles; Mobile Phase A: 5:95 MeCN:H20 with 10- mM aq. NH4OAc; Mobile Phase B: 95:5 MeCN:H20 with l0-mM aq. NH4OAc; Gradient: 10-50% B over 27 min, then a 5-min hold at 100% B; Flow: 20 mL/min) to give Example 250 (1.1 mg, 9% yield; 100% purity by LC/MS). LCMS [M + H]+ = 483.1. NMR (500 MHz, DMSO-i/e) d 8.28 (d, J= 5.7 Hz, 1H), 7.86 (d, J= 8.5 Hz, 1H), 7.51 (d, j= 8.7 Hz, 1H), 6.50 (d, j= 5.7 Hz, 1H), 6.00 (s, 2H), 5.18 – 5.07 (m, 1H), 4.72 (s, 1H), 4.11 (s, 3H), 2.26 (s, 3H), 1.91 – 1.43 (m, 8H), 1.18 (d, j= 6.2 Hz, 6H; the proton a to the carboxylic acid is not observed due to water-suppression). hLPAi IC50 = 41 nM.

Statistics shows that 1250967-81-7 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-4-isopropoxypyrimidine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SHI, Yan; WANG, Ying; CHENG, Peter Tai Wah; SHI, Jun; TAO, Shiwei; CORTE, James R.; FANG, Tianan; LI, Jun; KENNEDY, Lawrence J.; KALTENBACH, III, Robert F.; JUSUF, Sutjano; (316 pag.)WO2019/126093; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia