Tag: M.W:100-200

5750-76-5, 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. 5750-76-5, name is 2,4,5-Trichloropyrimidine, molecular formula is C4HCl3N2, 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.

2-iodoaniline (17.5 g, 79.9 mmol) and dimethyl phosphine oxide (6.9 g, 88.5 mmol) were added,Palladium acetate (0.3 g, 1.3 mmol), Xantphos (0.77 g, 1.3 mmol),N,N-diisopropylethylamine (22.7 g, 175.8 mmol), DMF (50 mL),Magnetic stirring. Under nitrogen protection, heat to 100C for 6 hours,The 2-iodoaniline consumption was monitored by thin layer chromatography. Cool to room temperature2,4,5-trichloropyrimidine (17.5 g, 95.9 mmol) was added and the reaction was heated to 75C for 6 hours.The reaction was complete by thin layer chromatography. Cool to room temperature, add water 300mL,Adjust pH to 5 with 5% hydrochloric acid and extract with ethyl acetate (100 mL x 3).Wash with sodium bicarbonate solution (100 mL), wash with saturated sodium chloride solution (100 mL ¡Á 2),Dry over anhydrous sodium sulfate. It is filtered with suction and concentrated to give a crude brown solid.Recrystallization with ethyl acetate/petroleum ether (volume ratio 1:2) gave an almost white solid 17g.Yield 67.3%.

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. 5750-76-5, 2,4,5-Trichloropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Changzhou Engineering Polytechnic College; Zhou Haiping; Qiu Yuejin; Bao Xiaobo; Liu Qiaoyun; Ni Yinggang; (7 pag.)CN107522742; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

3934-20-1, A common compound: 3934-20-1, name is 2,4-Dichloropyrimidine,molecular formula is C4H2Cl2N2, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

To a stirred solution of 2,4-dichloropyrimidine (3.00 g, 20.1 mmol) in toluene (25 mL) was added 4-fluorophenylboronic acid (2.82 g, 20.1 mmol), potassium carbonate (8.32 g, 60.3 mmol), tetrakis(triphenylphosphine)palladium(0) (0.630 g, 0.545 mmol) and 1 : 1 (v/v) ethanol/water (36 mL). The mixture was heated at 55 C for 12 hours and then concentrated. The residue was diluted with water and extracted with ethyl acetate. The combined extracts were washed with brine, dried (Na2S04) and concentrated. The crude material was purified by flash chromatography over silica using a hexane/ethyl acetate eluant to afford 2-chloro-4-(4-fluorophenyl)pyrimidine as a yellow solid (2.50 g, 61%). To a stirred solution of this compound (1.27 g, 6.09 mmol) in N,N-dimethylformamide (8 mL) was added ethyl piperidine-4-carboxylate (0.959 g, 6.10 mmol) and cesium carbonate (2.10 g, 6.44 mmol). The mixture was heated at 100 C for 12 hours and then concentrated. The residue was diluted with water and extracted with ethyl acetate. The combined extracts were washed with brine, dried (Na2S04) and concentrated. The crude material was purified by flash chromatography over silica using a hexane/ethyl acetate eluant to afford ethyl l-(4′-fluoro-[l, -biphenyl]-3-yl)piperidine-4-carboxylate as a yellow oil (1.60 g, 80%>). To a stirred solution of this intermediate (1.60 g, 4.80 mmol) in 1 : 1 (v/v) methanol/water (20 mL) was added solid sodium hydroxide (0.968 g, 24.2 mmol). After 2 hours, the reaction was concentrated. The residue was dissolved in water, made acidic (pH ~6) with the addition of IN hydrochloric acid and extracted with ethyl acetate. The combined organic layers were washed with brine, dried (Na2S04) and concentrated to afford l-(4′-fluoro-[l, -biphenyl]-3-yl)piperidine-4-carboxylic acid as a white solid (1.40 g, 97%). Using General Procedure D and Intermediate 5, this carboxylic acid was subjected to amide coupling to generate the title compound as a white solid (0.118 g, 27%). FontWeight=”Bold” FontSize=”10″ Eta NuMuKappa (500 MHz, CDC13) delta 8.37 (d, J= 5.0 Hz, 1H), 8.07-8.04 (m, 2H), 7.15 (t, J= 9.0 Hz, 2H), 6.89 (d, J= 10.0 Hz, 1H), 5.38 (s, 1H), 4.97-4.95 (m, 2H), 3.02-2.83 (m, 8H), 2.39-2.37 (m, 2H), 1.96-1.51 (m, 13H) ppm. 13C NMR (100 MHz, CDCI3) delta 174.1, 165.3, 163.3, 163.2, 161.7, 158.4, 133.8, 129.0, 128.9, 115.7, 115.5, 105.2, 59.4, 53.1, 47.6, 46.1, 44.6, 43.5, 39.3, 36.1, 28.9, 28.7, 25.1, 24.3, 24.2 ppm. Purity: >96% (214 & 254 nm) LCMS; retention time: 1.44 min; (M+H+) 438.3.

With the rapid development of chemical substances, we look forward to future research findings about 3934-20-1.

Reference:
Patent; GENZYME CORPORATION; BOURQUE, Elyse; CABRERA-SALAZAR, Mario, A.; CELATKA, Cassandra; CHENG, Seng, H.; HIRTH, Bradford; GOOD, Andrew; JANCSICS, Katherine; MARSHALL, John; METZ, Markus; SCHEULE, Ronald, K.; SKERLJ, Renato; XIANG, Yibin; ZHAO, Zhong; LEONARD, John; NATOLI, Thomas; MAKINO, Elina; HUSSON, Herve; BESKROVNAYA, Oxana; WO2014/43068; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 3934-20-1, name is 2,4-Dichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. 3934-20-1

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). Evaporation of solvent gave a yellow residue which was purified by Prep. HPLC to afford a yellowish oil as 2-chloro-4-phenyl-pyrimidine.

Statistics shows that 3934-20-1 is playing an increasingly important role. we look forward to future research findings about 2,4-Dichloropyrimidine.

Reference:
Patent; Bristol-Myers Squibb Company; US2008/107623; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

7752-82-1 ,Some common heterocyclic compound, 7752-82-1, molecular formula is C4H4BrN3, 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.

c) 6-Bromo-imidazof1w2-alPyrimidine; 50 mmol of 5-bromo-pyrimidin-2-ylamine are dissolved in 200 mi of saturated aqueous sodium hydrogencarbonate solution. 55 mmol of chloroacetaldehyde are added to the reaction mixture and the mixture is stirred for 24 hours at 25C. The mixture is extracted with ethyl acetate (3×300 ml) and the combined extracts are dried over sodium sulphate and evaporated under reduced pressure. Flash chromatography (SiO2 60F) of the residue provides the title compound which is identified on the basis of its Rf-value

According to the analysis of related databases, 7752-82-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SPEEDEL EXPERIMENTA AG; WO2005/90304; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

32779-36-5, Adding a certain compound to certain chemical reactions, such as: 32779-36-5, 5-Bromo-2-chloropyrimidine, 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, 32779-36-5, blongs to pyrimidines compound.

Intermediate 191 ,1 -dimethylethyl 4-(5-brom -2-pyrimidinyl)-1 -piperazinecarboxylateIn a microwave vial were mixed: 1 ,1 -dimethylethyl 1 -piperazinecarboxylate (1 10 mg, 0.589 mmol, available from Fluka), 5-bromo-2-chloropyrimidine (95 mg, 0.491 mmol, available from Lancaster) and DIPEA (0.1 12 mL, 0.638 mmol) in tert-butanol (2 mL). The reaction was stirred and heated in an Emrys Optimizer microwave at 150C for 0.5 hr. The reaction mixture was partitioned between EtOAc (20mL) and water (20mL) and the organic layer washed with brine (20mL) before being dried through an hydrophobic frit and concentrated to yield the desired product (162.3 mg)LCMS (Method C): Rt = 1.26, MH+ = 343

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,32779-36-5, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE LLC; DEMONT, Emmanuel, Hubert; GARTON, Neil, Stuart; GOSMINI, Romain, Luc, Marie; HAYHOW, Thomas, George, Christopher; SEAL, Jonathan; WILSON, David, Matthew; WOODROW, Michael, David; WO2011/54841; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

1004-38-2, 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. 1004-38-2, name is 2,4,6-Triaminopyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of 2,4,6-triaminopyrimidine 1 (1.0 mmol), 3-(2-cyanoacetyl)indole 2 (1.0 mmol), appropriate aromatic aldehyde (1.0 mmol) and indium chloride (0.05 mmol) in ethanol (5.0 mL) were subjected to microwave irradiation for 10 min at 120 C. After completion of the reaction (monitored by TLC using a dichloromethane-ethanol (9:1) mixture as the mobile phase), the reaction mixture was cooled and filtered. The solid product obtained was initially washed with ethanol, and finally recrystallized from ethanol.

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, 1004-38-2, 2,4,6-Triaminopyrimidine.

Reference:
Article; Enriz, Ricardo D.; Tosso, Rodrigo D.; Andujar, Sebastian A.; Cabedo, Nuria; Cortes, Diego; Nogueras, Manuel; Cobo, Justo; Vargas, Didier F.; Trilleras, Jorge; Tetrahedron; vol. 74; 49; (2018); p. 7047 – 7057;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 32779-36-5, 5-Bromo-2-chloropyrimidine, 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, 32779-36-5, blongs to pyrimidines compound. 32779-36-5

In a pressure tube with one end sealed, add 193 mg 5-bromo-2-chloropyrimidine (1.0 mmol) and 285 mg cyclopropylamine (5.0 mmol) in 3.0 mL ethanol, and the mixture is heated to 80 ¡ãCand stirred for 3 h. The reaction mixture was cooled to room temperature, and 203 mg solid product was collected by filitration for direct useyield: 95percent).MS (ESI), m/z: 215 (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,32779-36-5, its application will become more common.

Reference:
Patent; Guangzhou Institute Of Biomedicine And Health, Chinese Academy Of Sciences; DING, Ke; WANG, Deping; PEI, Duanqing; ZHANG, Zhang; SHEN, Mengjie; LUO, Kun; FENG, Yubing; EP2594567; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

96702-03-3 ,Some common heterocyclic compound, 96702-03-3, molecular formula is C6H10N2O2, 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 8 6-Carboxy-2-methyl-1,4,5,6-tetrahydropyrimidinium palmitate 20 g of ectoin are dissolved in 25 ml of water in a 250 ml plastic beaker with magnetic stirrer, and 36.894 g of palmitic acid are subsequently added at room temperature with stirring. This reaction mixture is stirred at room temperature for a further half an hour and subsequently evaporated to dryness in a rotary evaporator with a water bath at about 90 C., leaving a white solid. Melting point 61 C.

According to the analysis of related databases, 96702-03-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK PATENT GESELLSCHAFT; US2011/152292; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

271-80-7, 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. 271-80-7, name is 1H-Pyrazolo[3,4-d]pyrimidine, molecular formula is C5H4N4, 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.

520 mg (4.331 mmol) of 1H-pyrazolo[3,4-d]pyrimidine and 1.461 g (6.496 mmol) of N-iodosuccinimide were dissolved in 10 ml of DMF and the mixture was heated at 80 C. for 3 h. After cooling, the mixture was concentrated on a rotary evaporator and the residue was stirred with dichloromethane, filtered off with suction and dried under high vacuum. 569 mg (53% of theory) of the target compound were obtained. LC-MS (Method 3): Rt=1.23 min; MS (ESIpos): m/z=247 (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. 271-80-7, 1H-Pyrazolo[3,4-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; FOLLMANN, Markus; STASCH, Johannes-Peter; REDLICH, Gorden; GRIEBENOW, Nils; LANG, Dieter; WUNDER, Frank; PAULSEN, Holger; Huebsch, Walter; US2013/210824; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

A common compound: 7752-82-1, name is 5-Bromopyrimidin-2-amine,molecular formula is C4H4BrN3, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below., 7752-82-1

Conditions B (procedure using an in situ prepared boronic or boronate partner, see example 9) The halogenated substrate (1 eq), bis(pinacolato)diboron (1-2 eq), a suitable base (usually potassium acetate (1-6 eq), a suitable palladium catalyst with its ligands (usually Pd(dppf)Cl2.DCM 1-30 mol%) are stirred in a degassed solvent (usually dimethylformamide) at 60-120C for 1-16h under argon. After cooling down to room temperature, the halogenated tricyclic template (3-(7-bromo-imidazo[1,2-a]quinoxalin-4-ylamino)-propan-1-ol or 3-(7-iodo-imidazo[1,2-a]quinoxalin-4-ylamino)-propan-1-ol) (0.5 eq) is added with base (usually an aqueous solution of sodium or potassium carbonate, 1-6 eq) and a suitable palladium catalyst (usually Pd(PPh3)4 1-30 mol%). The resulting mixture is stirred under argon at 60-120C for 2 to 48h. Concentration, partition (water / ethyl acetate), extraction of the aqueous phase (ethyl acetate), reunion of the organic phases, drying over sodium or magnesium sulfate and purification by flash chromatography or prep TLC over silicagel using a suitable eluent (usually a mixture dichloromethane / methanol or cyclohexane / ethyl acetate or dichloromethane / ethyl acetate or dichloromethane / methanol / ammonia) affords the desired compound. The following examples were prepared according to these procedures. The following table provides a summary of the operating conditions. Example 20: 3-{[1-(2-aminopyrimidin-5-yl)-7-(trifluoromethyl)imidazo[1,2-a]quinoxalin-4-yl]amino}propan-1-ol [Show Image] Prepared as mentioned beforehand 1H NMR (DMSO-d6), delta (ppm): 8.45 (s, 2H), 8.05 (t, J = 5.7 Hz, 1 H), 7.82 (s, 1 H), 7.66 (d, J = 8.6 Hz, 1 H), 7.58 (s, 1 H), 7.45 (d, J = 8.6 Hz, 1H), 7.15 (s, 2H), 4.62 (t, J = 5.1 Hz, 1 H), 3.65 (q, J = 6.3 Hz, 2H), 3.54 (q, J = 6.0 Hz, 2H), 1.84 (qt, J = 6.6 Hz, 2H) ESI-MS m/z 404 (M+H)+

With the rapid development of chemical substances, we look forward to future research findings about 7752-82-1.

Reference:
Patent; Mutabilis SA; EP1972629; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia