Day: August 5, 2021

Adding a certain compound to certain chemical reactions, such as: 6299-85-0, Methyl 2,6-dichloropyrimidine-4-carboxylate, 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, COA of Formula: C6H4Cl2N2O2, blongs to pyrimidines compound. COA of Formula: C6H4Cl2N2O2

(1) To a solution of methyl 2,4-dichloropyrimidine-6-carboxylate (1.00 g, 4.83 mmol) and triethylamine (0.940 mL, 6.76 mmol) in N,N-dimethylformamide (6.0 mL) was added 4-aminotetrahydro-2H-pyran (537 mg, 5.31 mmol) at 0 C. After being stirred for 3.5 hour at 0 C., the reaction mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1 to 1:2) to give methyl 2-chloro-6-(tetrahydro-2H-pyran-4-ylamino)pyrimidin-4-carboxylate as a colorless solid (1.12 g, 85%). mp 190-192 C. MS (APCI): m/z 272/274 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6299-85-0, Methyl 2,6-dichloropyrimidine-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Kawanishi, Eiji; Matsumura, Takehiko; US2011/160206; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 50270-27-4 ,Some common heterocyclic compound, 50270-27-4, molecular formula is C5HCl3N2O, 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.

Method H: compound 10 (211 mg, 1.0 mmol) was dissolved in ethanol (5 mL) and stirred at -78 C., to which was slowly added hydrazine hydrate (53 muL, 1.1 mmol), monitored by TLC until complete reaction, to which was added ethyl acetate (50 mL). The system washed with water once, and the organic phase was dried with anhydrous sodium sulfate, filtered, concentrated and separated by silica gel column chromatography to obtain compound 11a (127 mg, 67% yield). MS (ESI) m/z: 190 [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. 50270-27-4, 2,4,6-Trichloropyrimidine-5-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Xiamen University; Deng, Xianming; Huang, Wei; Sun, Xihuan; Zhang, Ting; He, Zhixiang; Liu, Yan; Wu, Xinrui; Zhang, Baoding; Li, Xiaoyang; Zhang, Jingfang; Chen, Yun; Li, Li; Xu, Qingyan; Hu, Zhiyu; (206 pag.)US2020/165246; (2020); 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. 10457-14-4, name is 2,4-Bis((trimethylsilyl)oxy)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

To a solution of 2,4-bis(trimethylsilyloxy)pyrimidine (4.58 g, 17.84 mmol) in anhydrous methylene chloride (30 mL) was added a solution of [[2-(4-bromobenzyloxy)ethoxy]methoxy]methyl chloride (18) (5.0 g, 17.88 mmol) in methylene chloride (20 mL) and stirred for 16 h at room temperature. Ethanol (95%, 10 mL) was added and the resulting mixture was stirred for 30 min, filtered, evaporated to dryness under reduced pressure and purified by short-column flash chromatography using a mixture of CHCl3/EtOH (10:1). Analytical sample was recrystallized from ethyl acetate to give compound 19 as white crystals (4.25 g, 67%), mp 103.5-104.5 C, Rf 0.39 (ethyl acetate); 1H NMR (400 MHz, DMSO-d6): delta 3.54 (2H, dd, J = 5.9 and 3.2 Hz, CH2), 3.66 (2H, dd, J = 5.5 and 3.5 Hz, CH2), 4.44 (2H, s, NCH2), 5.10 (2H, s, OCH2), 5.60 (1H, d, J = 7.8 Hz, Ura-H-5), 7.26 (2H, d, J = 8.3 Hz, H-2′, H-6′), 7.52 (2H, d, J = 8.3 Hz, H-3′, H-5′), 7.70 (1H, d, J = 8.1 Hz, Ura-H-6), 11.33 (1H, s, NH); 13C NMR (100 MHz, DMSO-d6): delta 68.4, 69.2, 71.5, 76.9, 101.9, 120.7, 129.8, 131.5, 138.2, 145.3, 151.4, 163.9.

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, 10457-14-4, 2,4-Bis((trimethylsilyl)oxy)pyrimidine.

Reference:
Article; Babkov, Denis A.; Khandazhinskaya, Anastasia L.; Chizhov, Alexander O.; Andrei, Graciela; Snoeck, Robert; Seley-Radtke, Katherine L.; Novikov, Mikhail S.; Bioorganic and Medicinal Chemistry; vol. 23; 21; (2015); p. 7035 – 7044;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 148550-51-0, 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. 148550-51-0, name is Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate, molecular formula is C8H10N2O4S, 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.

Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate (2.15 g, 9.34 mmol) was dissolved in acetonitrile (11.7 ml), and, with stirring at room temperature, aqueous 32percent ammonium hydroxide (11.36 ml, 93 mmol) was added drop wise. A white suspension was obtained after few seconds. Acetonitrile was evaporated and the aqueous suspension was filtered on a buckner funnel. The obtained solid was washed with water (20 ml) and dried affording ethyl 2-aminopyrimidine-5-carboxylate as a white solid (1.192 g, 7.13 mmol, 76percent yield, MS/ESI+ 168.1 [MH]+).

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 148550-51-0, Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate.

Reference:
Patent; Chiesi Farmaceutici S.p.A.; ARMANI, Elisabetta; Amari, Gabriele; Capaldi, Carmelida; Esposito, Oriana; Peretto, Ilaria; US2013/79313; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 16075-42-6, 2-Amino-4-(trifluoromethyl)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, name: 2-Amino-4-(trifluoromethyl)pyrimidine, blongs to pyrimidines compound. name: 2-Amino-4-(trifluoromethyl)pyrimidine

General procedure: Two mmol 5b1-5b20 was added to a dichloromethane solution containing 0.3 mL triethylamine at 0 C. Then 1.2 equiv. 3-chloropropionyl chloride was dissolved in dry dichloromethane, and the obtained mixture was slowly added to the aniline solution at 0 C. The reaction mixture was allowed to slowly warm up to room temperature, extracted with dichloromethane and finally washed with 2 M HCl. The organic phase was combined and dried with anhydrous MgSO4. Filtration and removal of the solvent under reduced pressure gave the crude product. The desired product was further purified by flash column chromatography with petroleum ether-EtOAc (20:1 to 10:1) to produce 6b1-6b20.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16075-42-6, 2-Amino-4-(trifluoromethyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Zhu, Kongkai; Song, Jia-Li; Tao, Hong-Rui; Cheng, Zhi-Qiang; Jiang, Cheng-Shi; Zhang, Hua; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3693 – 3699;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 90349-23-8, 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid, 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, 90349-23-8, blongs to pyrimidines compound. SDS of cas: 90349-23-8

To a stirred solution of 5,7-dimethylpyrazolo[l,5-a]pyrimidine-3-carboxylic acid 2 (50 mg, 0.262 mmol), 2-methyl-lH-l,3-benzodiazol-6-amine (57 mg, 0.314 mmol) and HATU (149 mg, 0.393 mmol) in DMF (1 mL) was added DIPEA (0.14 mL, 0.786 mmol), and the reaction mixture was stirred at room temperature for 16 hours until the reaction was complete. The suspension was diluted with H20 (3 mL), and the precipitated solid was collected by filtration, washed with minimum DCM and Et20, and purified by prep-HPLC (MeCN/10 mM NH4HCO3) to give the title compound (28 mg, 33%) as a white solid.XH NMR (400 MHz, DMSO-i/6) 5 12.16 (s, 1H), 10.18 (d, J= 31.2 Hz, 1H), 8.63 (s, 1H), 8.09 (d, J= 53.2 Hz, 1H), 7.49-7.16 (m, 3H), 2.78 (s, 3H), 2.72 (s, 3H), 2.49 (s, 3H). ES-MS m/z: 321.1 [M+H]+. LC-MS Purity (254 nm): 99%; tR= 1.46 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,90349-23-8, its application will become more common.

Reference:
Patent; LYSOSOMAL THERAPEUTICS INC.; SKERLJ, Renato, T.; LANSBURY, Peter, T.; GOOD, Andrew, C.; BOURQUE, Elyse, Marie Josee; (139 pag.)WO2016/73895; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 22536-61-4, 2-Chloro-5-methylpyrimidine, 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, 22536-61-4, blongs to pyrimidines compound. HPLC of Formula: C5H5ClN2

A solution of 2-chloro-5-methylpyrimidine (500 g, 3889 mmol, 1.0 equiv) in DMF (5000 mL) was degassed with N2 for 20 mm and then dppf (108 g, 194 mmol, 0.05 equiv) and Pd2(dba)3 (178 g, 194 mmol, 0.05 equiv) were added to the reaction mixture. Zn(CN)2 (685 g, 5834 mmol, 1.5 equiv) was added, and the reaction mixture was heated at 100 C for 16 h. The reaction was quenched with water (5 L) and stirred for 10 mm. The reaction mixture was filtered through Celite brand filter aid pad. The filtrate was diluted with water (4 L) and extracted with EtOAc (2 x 4 L). The combined organic layers were washed with brine (4 L), dried over Na2SO4, filtered, and concentrated in vacuo to give the initial productwhich was further purified by column chromatography using silica gel (60-120 mesh) and0-10 % EtOAc in hexane to obtain Example 374.01 (330 g, 71 %) as an off white solid.1H NMR (400 MHz, DMSO-d6) oe 8.89 (s, 2H), 2.39 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22536-61-4, its application will become more common.

Reference:
Patent; AMGEN INC.; BROWN, Matthew; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HOUZE, Jonathan; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YEH, Wen-Chen; (815 pag.)WO2018/97944; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 3934-20-1, 2,4-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, Formula: C4H2Cl2N2, blongs to pyrimidines compound. Formula: C4H2Cl2N2

Example 90 Preparation of Intermediate 90 To a solution of 2,4-dichloropyrimidine (149 mg, 1 mmol) in THF (5 mL), tetrakis(triphenylphosphine)palladium (23 mg, 2 mol %) and 0.5M solution of phenylzinc bromide (2.1 mL, 1.05 mmol) in THF were added. The reaction mixture was stirred at 50 C. for overnight. Then it was added saturated ammonium chloride solution and extracted with EtOAc twice. The organic layers were combined, washed with water and dried (MgSO4). Filtration and concentration of solvent gave a yellow residue which was purified by Prep. HPLC to afford a yellowish oil as 2-chloro-4-phenyl-pyrimidine.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3934-20-1, 2,4-Dichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Sin, Ny; Good, Andrew Charles; Venables, Brian Lee; Scola, Paul Michael; Meanwell, Nicholas A.; US2006/183694; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 23945-44-0, 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.23945-44-0, name is 2,4-Dihydroxypyrimidine-5-carboxylic acid, molecular formula is C5H4N2O4, molecular weight is 156.0963, as common compound, the synthetic route is as follows.

Example 9; 7-Amino-8-ethyl-5-oxo-2-[4-(3-pyridin-3-ylmethylureido)phenyl]-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic Acid Methylamide (No. 53)9.1: 2,4-Dihydroxypyrimidine-5-carbonyl Chloride In a 250 ml round-bottomed flask, under a nitrogen atmosphere, 10.0 g (64.0 mmol) of 2,4-dihydroxypyrimidine-5-carboxylic acid are dissolved in 46 ml (500.0 mmol) of POCl3. The temperature of the mixture is reduced to 0 C. by means of an ice bath, and then 47.7 g (230 mmol) of PCl5 are added in small portions. The solution is stirred for 16 h at reflux and the solvents are then evaporated off under reduced pressure. The residue is taken up and triturated in 100 ml of toluene and then filtered. This operation is repeated three times and then the filtrate is evaporated under reduced pressure, so as to give 13.5 g (64.0 mmol) of compound in the form of a yellow oil which is used directly for the next stage. Yield=100%.

Statistics shows that 23945-44-0 is playing an increasingly important role. we look forward to future research findings about 2,4-Dihydroxypyrimidine-5-carboxylic acid.

Reference:
Patent; SANOFI-AVENTIS; US2011/251194; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 287714-35-6, Methyl 2-chloropyrimidine-5-carboxylate, 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, 287714-35-6, blongs to pyrimidines compound. Safety of Methyl 2-chloropyrimidine-5-carboxylate

A solution of methyl 2-chloropyrimidine-5-carboxylate (900 mg, 5.22 mmol) in dichloromethane (7.50 ml) was added to a stirred suspension of 2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine, HCl (1106 mg, 6.26 mmol) and N-ethyl-N-propan-2-ylpropan-2-amine (3.19 mL, 18.25 mmol) in dichloromethane (13.00 mL) at room temperature under nitrogen. The resulting solution was stirred at ambient temperature for 18 h. The reaction mixture was poured onto ice (50 mL), extracted with DCM (3×50 mL), the organic layer was dried over MgSO4, filtered and evaporated to afford yellow solid. The crude product was purified by crystallisation from IPA to afford the title compound (591 mg, 41%) as a white solid. The filtrate still contained some product and was purified by silica column chromatography, eluting with a gradient of 0 to 10% 7M NH3/MeOH in dichloromethane. Pure fractions were evaporated to dryness to afford a further sample of the title compound (402 mg, 28%) as a white solid. 1H NMR (399.9 MHz, DMSO-d6) delta 1.14-1.30 (2H, m), 1.46-1.55 (1H, m), 1.61 (2H, d), 1.72 (1H, d), 1.81 (1H, t), 1.95 (1H, m), 2.06 (1H, m), 2.67-2.70 (1H, m), 2.80 (2H, d), 3.05-3.12 (1H, m), 3.81 (3H, s), 4.59 (1H, m), 4.68 (1H, d), 8.79 (2H, s). MS: m/z 277 (MH+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,287714-35-6, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; US2008/153812; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia