Day: April 27, 2021

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.23906-13-0, name is 2-Hydrazinyl-4,6-dimethylpyrimidine, molecular formula is C6H10N4, molecular weight is 138.17, as common compound, the synthetic route is as follows.COA of Formula: C6H10N4

General procedure: To a solution of 0.2 g (3.6 mmol) of potassium hydroxide in 20 mL of ethanol was added successively 0.5 g (3.6 mmol) of hydrazine 5 and 3.6 mmol of an appropriate 3-aryl-1-phenyl-2-propen-1-one 4a-4d. The mixture was boiled for 2 h and cooled to room temperature. The separated precipitate was filtered off, washed with a minimal quantity of ethanol cooled to 5C, recrystallized from an appropriate solvent or mixture of solvents, and dried to a constant weight. Further physicochemical and spectral characteristics are listed for the products purified by crystallization.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,23906-13-0, 2-Hydrazinyl-4,6-dimethylpyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Erkin; Yuzikhin; Krutikov; Russian Journal of Organic Chemistry; vol. 52; 8; (2016); p. 1173 – 1178; Zh. Org. Khim.; vol. 52; 8; (2016); p. 1181 – 1185;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 51940-64-8, 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 51940-64-8, name is Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate. This compound has unique chemical properties. The synthetic route is as follows.

In a 20 mL vial, (R)-3-amino-10-methyl-9,10,11,12-tetrahydro-8H-[1,4]diazepino[5?,6?:4,5]thieno[3,2-f]quinolin-8-one (INT-3) (0.095 g, 0.318 mmol), ethyl 2,4-dichloropyrimidine-5-carboxylate (0.084 g, 0.382 mmol), and Huenig’s Base (0.111 ml, 0.637 mmol) were added to 5 mL of i-PrOH. The vial was sealed and the suspension warmed to 95 C. for 24 hours. Once determined to be complete, the reaction was cooled and a precipitate formed. 5 mL of ethyl ether was added, the vial was sonicated briefly, and the product was isolated by filtration to afford compound I-18 (0.112 g, 0.232 mmol, 72.8% yield). 1H NMR (400 MHz, DMSO-d6): delta 1.18 (d, J=6.7 Hz, 3H), 1.35 (t, J=7 Hz, 3H), 3.42-3.46 (m, 2H), 3.60 (m, 1H), 4.39 (q, J=7 Hz, 2H), 7.08 (br s, 1H), 7.81 (d, J=9.0 Hz, 1H), 8.06 (d, J=4 Hz, 1H), 8.10 (d, J=9.0 Hz, 1H), 8.54 (d, J=9.2 Hz, 1H), 8.93 (s, 1H), 9.27 (d, J=9.3 Hz, 1H), 10.99 (s, 1H). MS m/z (M+H): 483.29.

According to the analysis of related databases, 51940-64-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Celgene Avilomics Research, Inc.; Alexander, Matthew David; Chuaqui, Claudio; Malona, John; McDonald, Joseph John; Ni, Yike; Niu, Deqiang; Petter, Russell C.; Singh, Juswinder; (164 pag.)US2016/75720; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1445-39-2, Adding some certain compound to certain chemical reactions, such as: 1445-39-2, name is 2-Amino-5-iodopyrimidine,molecular formula is C4H4IN3, 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 1445-39-2.

5-[(3-aminophenyl)ethynyl]pyrimidin-2-amine 2-Amino-5-iodopyrimidine (2.21 g), bis(triphenylphosphine)palladium dichloride (350 mg) and copper(I) iodide (40 mg) were stirred in DMF (100 mL)-triethylamine (20 mL) and degassed with nitrogen for 10 min. 3-Ethynyl aniline (1.29 g) was added and the mixture heated to 95 C. for 2 hours. The solvent was evaporated and the residue was purified by trituration with DCM (20 mL) to give the title compound as a brown solid (1.25 g, 60%); 1H NMR (DMSO-d6) 5.21 (bs, 2H), 6.58-6.70 (m, 3H), 7.03-7.07 (m, 3H), 8.40 (s, 2H); MS m/e MH+211.

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. 1445-39-2, 2-Amino-5-iodopyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; US2008/194552; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 461-98-3 ,Some common heterocyclic compound, 461-98-3, molecular formula is C6H9N3, 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 microwave tube was added 4-bromo-2-(2,6-dichlorophenyl)thiazolo[5,4-c]pyridine (60 mg, 0.17 mmol), 2,6-dimethylpyrimidin-4-amine (0.027 g, 0.22 mmol), Pd2(dba)3 (0.013 g, 0.017 mmol), XantPhos ((0.017 g, 0.034 mmol) and Cs2C03 (0.111 g, 0.34 mmol) in dioxane (3.0 mL). The mixture was degassed with N2 for 10 minutes and then irradiated in a microwave reactor at 160 C for 2 hours. After cooling to room temperature the solid was removed via filtration. The filtrate was concentrated under reduced pressure and the residue was purified with reverse phase column chromatography eluting with a 0-60% gradient of CH3CN in 0.5% NH4HC03 to give the desired product as a white solid (14 mg, 21% yield). ? NMR (500 MHz, CH3OH-??: delta 8.44 (d, J = 5.5 Hz, 1H), 7.71 (d, J = 5.5 Hz, 1H), 7.56-7.51 (m, 4H), 7.31 (s, 1H), 2.44 (s, 3H), 2.35 (s, 3H). LCMS (Method A): RT = 5.75 min, m/z: 402.0 [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,461-98-3, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLENCH, Toby; ELLWOOD, Charles; GOODACRE, Simon; LAI, Yingjie; LIANG, Jun; MACLEOD, Calum; MAGNUSON, Steven; TSUI, Vickie; WILLIAMS, Karen; ZHANG, Birong; WO2012/35039; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1780-26-3, 2-Methyl-4,6-dichloropyrimidine, 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 2-Methyl-4,6-dichloropyrimidine, blongs to pyrimidines compound. Quality Control of 2-Methyl-4,6-dichloropyrimidine

The crude 2-methyl-4,6-dichloropyrimidine (41.8 g.; 256 mmol) was dissolved in dichloromethane (200 mL) and chilled to -78C in an inert atmosphere. Morpholine (48 g.; 550 mol) dissolved in dichloromethane (100 mL) was added slowly. The reaction was allowed to warm to room temperature while stirring overnight. The organic layer was washed with saturated ammonium chloride (2×100 mL), dried with sodium sulfate, and evaporated to give 2-methyl-4-chloro-6-morpholino-pyrimidine (48.5 g.; 227 mmol).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1780-26-3, 2-Methyl-4,6-dichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; SYNTA PHARMACEUTICALS CORP.; WO2006/124662; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 262353-34-4 , The common heterocyclic compound, 262353-34-4, name is 2,4-Diiodopyrimidine, molecular formula is C4H2I2N2, 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.

General procedure: Compound 4 (1equiv per iodine atom), NEt3 (0.5mL), CuI (6mol%), and Pd(PPh3)2Cl2 (6mol%) were added to iododiazine (1mmol) in THF (5mL). The suspension was stirred at room temperature overnight under nitrogen atmosphere. The suspension was then diluted with a mixture of water and dichloromethane (1:1, 20mL) and the organic layer separated. The aqueous layer was extracted with dichloromethane (2¡Á20mL). The combined organic extracts were dried over MgSO4, filtered, and evaporated.

The synthetic route of 262353-34-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gauthier, Sebastien; Vologdin, Nikolay; Achelle, Sylvain; Barsella, Alberto; Caro, Bertrand; Robin-Le Guen, Francoise; Tetrahedron; vol. 69; 39; (2013); p. 8392 – 8399;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 720-01-4, 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. 720-01-4, name is Ethyl 4-chloro-2-trifluoromethylpyrimidine-5-carboxylate, molecular formula is C8H6ClF3N2O2, 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 solution of P(t-Bu)3 (0.32 g, 1.57 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (0.72 g, 0.78 mmol), in 10 ml of THF, stirred at room temperature for 30 min, the dark red heterogeneous solution Pd(P(t-Bu)3)2 formed. Then KF (2.74 g, 47.24 mmol), and 3,4-dimethoxyphenylboronicacid (2.15 g, 11.80 mmol) in dry THF (50ml) was added. Finally ethyl-4-chloro-2-(trifluoromethyl)pyrimidine-5-carboxylate (2g, 7.87 mmol), was added under N2 atmosphere. The reaction mixture was heated to 65C for 14 h. TLC showed the completion of the reaction. Then the mixture was cooled and concentrated under vacuo to get crude residue, which was purified by column chromatography over silica gel (Ethylacetate/ Hexane, 1:3) to afford title product as an off-white solid in 74% yield. ESI-MS: 357 (M+1).

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 720-01-4, Ethyl 4-chloro-2-trifluoromethylpyrimidine-5-carboxylate.

Reference:
Article; Purushothaman, Baskaran; Arumugam, Parthasarathy; Kulsi, Goutam; Song, Joon Myong; European Journal of Medicinal Chemistry; vol. 145; (2018); p. 673 – 690;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 582313-57-3, name is 4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine, the common compound, a new synthetic route is introduced below. Recommanded Product: 582313-57-3

Into a 100-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 4-chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine (700 mg, 4.08 mmol, 1.00 equiv) in tetrahydrofuran (40 mL), then compound 24a (1.528 g, 4.08 mmol, 1.00 equiv, J. Org. Chem. 2009, 74, 6819-6824) and triphenylphosphine (3.208 g, 12.24 mmol, 3.00 equiv) was added sequentially. This was followed by the addition of a solution of DEAD (2.131 g, 12.25 mmol, 3.00 equiv) in tetrahydrofuran (20 mL) dropwise with stirring at room temperature. The resulting solution was allowed to stir for 3 hours at room temperature,and then it was concentrated in vacuo. The resulting residue was purified using flash column chromatography on silica gel, eluting with ethyl acetate/petroleum ether (1:8) to provide 300 mg (14percent) of compound 24b as a white solid.

The synthetic route of 582313-57-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; VERMA, Vishal; ARASAPPAN, Ashok; NJOROGE, F. George; GIRIJAVALLABHAN, Vinay; BOGEN, Stephane, L.; DANG, Qun; OLSEN, David, B.; WO2013/9735; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 17321-93-6 ,Some common heterocyclic compound, 17321-93-6, molecular formula is C5H6BrN3, 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.

General procedure: The halo aryl (1.0 equiv) was dissolved in a mixture of water:dioxane (1:1). The boronic acid or ester(1.5 equiv) and potassium phosphate (5.0 equiv) were added. The solution was degassed byvacuum/argon cycles (10 times) before addition of PdCl2(PPh3)2 (10 molpercent) and further degassed (5times). The resulting mixture was stirred at 95 ¡ãC under argon atmosphere for 16-20 hours. Thereaction mixture was filtered through Celite and diluted with water (approx. 30 mL) before washingwith chloroform (3 x 30 mL). If not stated otherwise, the aqueous phase was concentrated underreduced pressure and applied to a C18 precolumn before purification on a 10g or 60 g C18 column witha gradient of acetonitrile in water (10-100percent) to yield the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17321-93-6, its application will become more common.

Reference:
Article; Akhter, Sundus; Lund, Bjarte Aarmo; Ismael, Aya; Langer, Manuel; Isaksson, Johan; Christopeit, Tony; Leiros, Hanna-Kirsti S.; Bayer, Annette; European Journal of Medicinal Chemistry; vol. 145; (2018); p. 634 – 648;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 374930-88-8 , The common heterocyclic compound, 374930-88-8, name is tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate, molecular formula is C13H19BrN4O2, 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.

Tri-isopropyl borate (1.18 g, 6.25 mmol) was added, dropwise to a magnetically stirred solution of 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate (1.72 g, 5.00 mmol) in THF (15 mL). The mixture was cooled to -70 oC and butyl lithium (3.91 mL, 6.25 mmol) was added, dropwise maintaining the temperature at -60 oC over 15 minutes. The mixture was then warmed to -20 oC over 20 minutes followed by the addition of acetic acid (0.501 mL, 8.75 mmol). The reaction mixture was then evaporated and the resultant residue suspended in methanol (2 mL) and water (15 mL) to which hydrogen peroxide (0.870 mL of a 35% w/v solution in water, 49.4 mmol) was introduced, dropwise with vigorous stirring. The reaction was stirred for 18 hours and the resultant precipitate was filtered and washed with water. The solid was partitioned between dichloromethane and water and the separated organic phase was dried (MgSO4), filtered and concentrated to yield tert-butyl 4-(5-hydroxypyrimidin-2-yl)piperazine-1-carboxylate (1.32 g, 92%) as a white solid, NMR Spectrum: (DMSOd6) 1.46 (s, 9H), 3.43 (m, 4H), 3.61 (m, 4H), 8.09 (S, 2H), 9.30 (s, 1H); Mass Spectrum: M+H+ 281.

The synthetic route of 374930-88-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; De Savi, Chris; Waterson, David; Pape, Andrew; Lamont, Scott; Hadley, Elma; Mills, Mark; Page, Ken M.; Bowyer, Jonathan; Maciewicz, Rose A.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 16; (2013); p. 4705 – 4712;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia