Month: March 2022

Application of 3438-55-9, 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. 3438-55-9, name is 5-Bromo-4-chloro-6-methylpyrimidine. A new synthetic method of this compound is introduced below.

PREPARATIVE EXAMPLE 6 dl-5-bromo-6-methyl-4-(alpha-methylbenzylamino)pyrimidine (compound number 314) 2.0 g (0.02 mol) of triethylamine and 2.4 g (0.02 mol) of dl-alpha-methylbenzylamine were added to a solution of 4.15 g (0.02 mol) of 5-bromo-4-chloro-6-methyl-pyrimidine in 50 ml of benzene, and the mixture was refluxed with stirring for 5 hours. Upon completion of the reaction, the reaction product was washed with water, dried over anhydrous sodium sulphate and the benzene was distilled off to leave an oil. This oil was then caused to crystallize using column chromatography (Wakogel C-200, eluted with a 1:1 mixture of benzene and ethyl acetate). Crystals were obtained and recrystallized from n-hexane to give 2.6 g of the desired product in the form of pale yellow prisms melting at 85-87 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3438-55-9, its application will become more common.

Reference:
Patent; Sankyo Company, Limited; Ube Industries, Limited; US4435402; (1984); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1159818-57-1, 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 1159818-57-1, name is 4-Amino-6-bromopyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 6-bromopyrimidin-4-amine (1.01 g, 5.80 mmol) and ammonia solution (25 mL) was stirred in a sealed tube at 125 C overnight, then cooled down to rt and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (v/v) = 1/15) to give the title compound as a yellow solid (0.46 g, yield 72%).MS (ESI, pos. ion) m/z: 111.2 [M+H]+; (ppm): 7.82 (s, 1H), 6.10 (s, 4H), 5.39 (s, 1H).

According to the analysis of related databases, 1159818-57-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; XI, Ning; LI, Minxiong; PENG, Ju; LI, Xiaobo; ZHANG, Tao; HU, Haiyang; CHEN, Wuhong; BAI, Changlin; KE, Donghua; CHEN, Peng; (281 pag.)WO2019/99311; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1801-06-5 ,Some common heterocyclic compound, 1801-06-5, molecular formula is C5H4ClFN2O, 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.

EXAMPLE AA1 : 5-(r(2S.5f?)-4-ethyl-2.5-dimethylpiperazin-1-vncarbonyl)-lambda/-(5-fluoro-2- methoxypyrimidin-4-yl)-6,6-dimethyl-1 ,4,5.6-tetrahvdropyrrolof3.4-clpyrazol-3-amine; A solution of 5-{[(2S,5f?)-4-ethyl-2,5-dimethylpiperazin-1-yl]carbonyl}-6,6-dimethyl- 1 ,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-3-amine (289 mg, 0.9 mmol) and 4-chloro-5- fluoro-2-methoxypyrimidine (257 mg, 2 eq) in 5 ml_ of 50percent acetic acid in water was heated in a microwave for 30 min at 8O0C. Purification as described in Example AJ. afforded the title compound AA1 as a white powder (13.1 mg, 3percent). See Table 1 below for NMR data.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1801-06-5, its application will become more common.

Reference:
Patent; PFIZER INC.; WO2008/96260; (2008); 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. 57401-76-0, name is Ethyl 2-aminopyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 57401-76-0

To a solution of ethyl 2-aminopyrimidine-5-carboxylate (0.200 g, 1.196 mmol) in DME (6 ml), a suspension of sodium 2-methylbutan-2-olate (0.527 g, 4.79 mmol) in DME (6 ml) was added drop wise stirring at room temperature under nitrogen. The resulting yellow suspension was stirred at the same temperature for 30 minutes and then cooled to -10C. Methanesulfonyl chloride (0.278 ml, 3.59 mmol) was added drop wise maintaining the temperature below – 5C. After 1.5 hours water (30 ml) was added and the mixture was extracted with ethyl acetate (20 ml x 3). The combined organic layers were dried over sodium sulfate and evaporated. The residue was triturated with MeOH and the mother liquors were evaporated and triturated with EtOH. The two portions collected by filtration were mixed affording 0.152 g of a mixture of ethyl 2-(methylsulfonamido)pyrimidine-5-carboxylate and methyl 2-(methylsulfonamido)pyrimidine-5-carboxylate (about 1 : 1 ratio). This mixture was suspended in THF (6.380 ml) and 3N NaOH (0.425 ml, 1.276 mmol) was added. The resulting solution was heated to 50C for 2.5 hours. THF was evaporated and the aqueous solution was diluted with water (2 ml) and acidified with 6N HC1 (pH = 2) stirring at room temperature. The obtained precipitate was collected by filtration affording 2-(methylsulfonamido)pyrimidine-5-carboxylic acid as a white solid (0.133 g, 0.612 mmol, 51.1% yield, MS/ESI+ 218.0 [MH] +).

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, 57401-76-0, Ethyl 2-aminopyrimidine-5-carboxylate.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; ARMANI, Elisabetta; AMARI, Gabriele; CAPALDI, Carmelida; ESPOSITO, Oriana; PERETTO, Ilaria; WO2013/45280; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 5267-07-2, 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 5267-07-2, name is 5-Pyrimidineacetic acid. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 4-bromobenzene-l ,2-diamine (10) (0.281g, 1.5mmol) , 2-(pyrimidin-5-yl)acetic acid (11) (0.207g, 1.5mmol), and HATU (0.741g, 1.95mmol) in DCM (50ml) was added triethylamine (0.63ml, 4.5mmol). The reaction mixture was stirred at room temperature overnight. The solution was washed with saturated sodium bicarbonate (50ml) and brine (50ml). The DCM solution was dried over sodium sulfate and concentrated. The residue was purified by automated column chromatography columned using DCM and methanol as eluents. Yield 0.4g, 87%. MS: m/z 306.9 (M+H+).

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 5267-07-2, 5-Pyrimidineacetic acid.

Reference:
Patent; ZALICUS PHARMACEUTICALS LTD.; PAJOUHESH, Hassan; HOLLAND, Richard; ZHANG, Lingyun; PAJOUHESH, Hossein; LAMONTAGNE, Jason; WHELAN, Brendan; WO2012/116440; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 213745-17-6, 4-Chloro-7-cyclopentyl-5-iodo-7H-pyrrolo[2,3-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, SDS of cas: 213745-17-6, blongs to pyrimidines compound. SDS of cas: 213745-17-6

To a pressure tube with dioxane (5 mL) was added 4-Chloro-7-cyclopentyl-5-iodo-7H- pyrrolo [2, 3-D] PYRIMIDINE, then ammonia hydroxide (5 mL). The pressure tube was sealed and heated at 120C overnight. All solvents were removed via reduced pressure, and the residue were purified through flash COLUMN (METHYLENE CHLORIDE/METHANOL : 97/3). The product was obtained as a white solid (300 mg, 92%). MS: 329.1 (MH+); HPLC Rf: 5.018 min.; HPLC purity: 99%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,213745-17-6, 4-Chloro-7-cyclopentyl-5-iodo-7H-pyrrolo[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2004/56830; (2004); A1;,
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. 34415-10-6, name is 2-Methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid, the common compound, a new synthetic route is introduced below. Recommanded Product: 2-Methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid

A mixture of 6-hydroxy-2-methylpyrimidine-4-carboxylic acid (500 mg) and phosphorus oxychloride (5 mL) was heated under reflux under a nitrogen atmosphere for 2 hr. The solvent was evaporated under reduced pressure. To the residue was added THF (3 mL). The reaction mixture was added dropwise to a mixture of 1-(3-fluoro-5-(1-methyl-1H-pyrazol-4-yl)phenyl)methanamine (732 mg), TEA (646 mg) and dichloromethane (8 mL) at 0C over 10 min, and the reaction mixture was stirred at the same temperature for 2 hr. The reaction mixture was diluted with water, and the aqueous layer was extracted with dichloromethane. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (198 mg) . MS: [M+H]+ 360.1.

The synthetic route of 34415-10-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; HIRAYAMA, Takaharu; HIRATA, Yasuhiro; TOMINARI, Yusuke; IWAMURA, Naoki; SASAKI, Yusuke; ASANO, Moriteru; TAKAGI, Terufumi; OKANIWA,Masanori; YOSHIDA, Masato; ICHIKAWA, Takashi; IMAMURA, Shinichi; (113 pag.)EP3514149; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 216309-28-3 , The common heterocyclic compound, 216309-28-3, name is 5-((Trimethylsilyl)ethynyl)pyrimidine, molecular formula is C9H12N2Si, 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.

(8S,9S)-9-epi-Azido-9-dehydroxy quinine (1.045 g, 3.0 mmol)was dissolved in a mixture of tert-butanol and water (12 mL, 1:1,v/v), and 2-(TMS-ethynyl)-pyrimidine (631 mg, 3.58 mmol,1.2 equiv) was added. Then pyridine (0.25 mL, 3.1 mmol,1.0 equiv), CuSO4.5H2O (290 mg, 1.25 mmol 0.4 equiv), sodiumascorbate (494 mg, 2.49 mmol, 0.8 equiv) and K2CO3 (806 mg,5.83 mmol, 1.9 equiv) were added. The suspension was stirred atroom temperature for 3 days. Then saturated aqueous Na2S solutionwas added and the mixture stirred for an additional 0.5 h,while dark brown precipitate formed. The mixture was filteredthrough Celite and washed with CH2Cl2. The filtrate was washedwith water, dried over Na2SO4 and evaporated. Chromatographyon silica gel (CHCl3/MeOH, 10:1 v/v.) gave white crystalline solid(1.233 g, 91%). M.p.: 248.53-250.7 C, [a]D21 = -182 (c 0.91, CH2Cl2).1H NMR (600 MHz, CDCl3) delta 8.81 (d, J = 4.4 Hz, 1H), 8.69 (d,J = 4.7 Hz, 2H), 8.15 (s, 1H), 7.99 (d, J = 9.1 Hz, 1H), 7.603-7.57(m, 1H), 7.50 (d, J = 4.7 Hz, 1H), 7.34 (dd, J = 9.1, 2.2 Hz, 1H), 7.11(t, J = 4.9 Hz, 1H), 6.51 (d, J = 11.3 Hz, 1H), 5.91 (ddd, J = 17.5,10.7, 6.9 Hz, 1H), 5.08 (d, J = 9.4 Hz, 1H), 5.06 (d, J = 18.2 Hz, 1H),3.94 (s, 3H), 3.933-3.88 (m, 1H), 3.493-3.42 (m, 1H), 3.14 (dd,J = 14.0, 10.1 Hz, 1H), 2.74 (dd, J = 14.3, 4.1 Hz, 1H), 2.713-2.65(m, 1H), 2.343-2.27 (m, 1H), 1.96 (t, J = 11.9 Hz, 1H), 1.793-1.76(m, 1H), 1.653-1.54 (m, 2H), 0.94 (dd, J = 14.1, 7.1 Hz, 1H)(Fig. S8a, SI).13C NMR (151 MHz, CDCl3) delta 159.1, 158.8, 157.4, 147.3, 147.2,145.1, 141.4, 138.8, 132.0, 128.2, 123.4, 122.6, 119.5, 119.2,114.8, 100.8, 61.0, 58.0, 56.1, 55.9, 41.1, 39.1, 27.74, 27.72, 27.70(Fig. S8a, SI).HRMS (ESI) Calc. for [C26H27N7O+H]+: 454.2350, found:454.2353 (Fig. S5, SI).

The synthetic route of 216309-28-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ga??zowska; Boraty?ski; Kowalczyk; Lipke; Czapor-Irzabek; Polyhedron; vol. 121; (2017); p. 1 – 8;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 186519-92-6, Adding some certain compound to certain chemical reactions, such as: 186519-92-6, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid,molecular formula is C7H4ClN3O2, 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 186519-92-6.

To a stirred suspension of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid (G-l) (3.11 g,15.7 mmol, 1.0 eq) and a catalytic amount of DMF in a mixture of DCM (40 mL) and THF (40 mL) at RT, oxalyl dichloride (2.0 mL, 23.5 mmol, 1.5 eq) is added dropwise. The resulting mixture is stirred for 2 h and then concentrated in vacuo. The residue (G2) is dissolved in DCM (50 mL) and the resulting solution is added dropwise to saturated aqueous ammonium hydroxide (200 mL) at RT. The resulting mixture is stirred for 30 min and then filtered. The filter cake is then rinsed with H20 (30 mL X 2). The filtrate is acidified with con. HC1 to adjust the pH to 4-5. The solid is collected by filtration, rinsed with water and dried in vacuo to afford the product, 4-chloro-7H-pyrrolo[2,3-d]pyrimidine- 5-carboxamide (G-3).

According to the analysis of related databases, 186519-92-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INTELLIKINE, INC.; INFINITY PHARMACEUTICALS, INC.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; CASTRO, Alfredo, C.; EVANS, Catherine, A.; WO2011/146882; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 4319-87-3, 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.4319-87-3, name is 5-Bromo-4-methoxy-6-methylpyrimidine, molecular formula is C6H7BrN2O, molecular weight is 203.04, as common compound, the synthetic route is as follows.

A mixture of 4-[3-methyl-4-(4,4,5,5-tetram ethyl-i ,3,2-d ioxaborolan-2-yl)phenoxy]furo[3,2- c]pyridine (C2) (4.0 g, ii mmol), 5-bromo-4-methoxy-6-methylpyrimidine (Z. Wang et al., Synthesis2Oll, 1529-1531)(2.Og, 10 mmol), [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (1.1 g, 1.4 mmol) and potassium carbonate (4.0 g, 29 mmol) in 1 ,4-dioxane (30 mL) containing 5 drops of water was heated at 120 00 for 2 hours. After filtration and concentration of the filtrate under reduced pressure, the residue was purified by silica gel chromatography (Eluent: 33% ethyl acetate in petroleum ether) to give the product as a yellow solid. Yield: 1.8 g, 5.2 mmol, 52%. 1H NMR (400 MHz, ODd3) oe8.72 (s, 1H), 8.07 (d, J=6.0 Hz, 1H), 7.66 (d, J=2.3 Hz, 1H), 7.25 (dd, J=5.9, 0.9 Hz, 1H), 7.19-7.21 (m, 1H), 7.09-7.16 (m, 2H), 6.88 (dd, J=2.3, 0.8 Hz, 1H), 3.95 (s, 3H), 2.29 (s, 3H), 2.07 (s,3H).

Statistics shows that 4319-87-3 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-4-methoxy-6-methylpyrimidine.

Reference:
Patent; PFIZER INC.; COE, Jotham, Wadsworth; ALLEN, John, Arthur; DAVOREN, Jennifer, Elizabeth; DOUNAY, Amy, Beth; EFREMOV, Ivan, Viktorovich; GRAY, David, Lawrence, Firman; GUILMETTE, Edward, Raymond; HARRIS, Anthony, Richard; HELAL, Christopher, John; HENDERSON, Jaclyn, Louise; MENTE, Scot, Richard; NASON, Deane, Milford, II; O’NEIL, Steven, Victor; SUBRAMANYAM, Chakrapani; XU, Wenjian; WO2014/72881; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia