Day: May 13, 2021

Related Products of 65996-50-1 ,Some common heterocyclic compound, 65996-50-1, molecular formula is C6H5N3O2, 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.

5.1.1.2 2,4-Dichloropyrrolo[3,2-d]pyrimidine (1) To pyrrolo[3,2-d]pyrimidin-2,4-dione 5 (2.00 g, 13.2 mmol), 1 N NaOH (15 mL), and 0.60 g NaOH in 15 mL H2O was added and the mixture stirred at 40 C until a clear solution was obtained. The solution was cooled to room temperature (21-25 C) and then placed in an ice bath to obtain thick slurry. The slurry was then filtered to obtain a pale yellow solid. The solid was dissolved in 1 N NaOH (15 mL), and heated to 40 C to obtain a clear solution that upon cooling provided white crystals. The crystals were washed with MeOH (20 mL) and acetone (20 mL), and then dried under vacuum. The dry solids were taken in phenylphosphonic dichloride (10 mL) and heated to 170-175 C for 5 h during which the reaction mixture became a brown-black solution. After 5 h the hot reaction mixture was poured onto ice, extracted with EtOAc (200 mL) and the organic layer washed with satd NaHCO3 solution (3* 100 mL) till all effervescence subsided. The organic layer was then washed with brine and dried over MgSO4. The organic layer was concentrated in vacuo and loaded onto silica. The product was purified using column chromatography eluting with 9:1 then 3:1 hexanes/EtOAc to obtain 1 as an off-white solid (1.50 g, 7.9 mmol, 60%). Rf 0.5 in 3:1 hexanes/EtOAc. Mp 228.3-232.0 C. 1H NMR (400 MHz, DMSO-d6): delta 6.71 (d, 1H, J = 3.2 Hz), 8.09 (d, 1H, J = 2.8 Hz), 12.75 (s, 1H, NH). 13C NMR (100 MHz, DMSO-d6): delta 103.2, 124.3, 138.0, 143.5, 149.6, 153.9. ESI-MS m/z for C6H3Cl2N3 calculated [M+H]+ 187.9776, found 187.9777.

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. 65996-50-1, 1H-Pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Temburnikar, Kartik W.; Ross, Christina R.; Wilson, Gerald M.; Balzarini, Jan; Cawrse, Brian M.; Seley-Radtke, Katherine L.; Bioorganic and Medicinal Chemistry; vol. 23; 15; (2015); p. 4354 – 4363;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.1514-96-1, name is 4-Chloro-2-(trifluoromethyl)pyrimidine, molecular formula is C5H2ClF3N2, molecular weight is 182.53, as common compound, the synthetic route is as follows.Quality Control of 4-Chloro-2-(trifluoromethyl)pyrimidine

(1) Phosphorus oxychloride (15 mL) was added to 2-trifluoromethyl-4-hydroxypyrimidine (2.50 g) and the mixture was stirred at 60C for 1 hr. The mixture was concentrated under reduced pressure, and a saturated aqueous sodium hydrogen carbonate solution was added to the residue. The mixture was extracted with ethyl acetate. The extract solution was washed with saturated brine, dried and concentrated under reduced pressure to give 2-trifluoromethyl-4-hydroxypyrimidine (0.600 g) as a brown oil.(2) Piperazine (845 mg) was dissolved in DMF (6 mL) with heating and a DMF solution (1 mL) of the above-mentioned compound (597 mg) were added at 40C. The mixture was stirred at room temperature for 2 hr. The reaction solution was concentrated under reduced pressure, and water was added to the residue. The mixture was extracted with chloroform. The extract solution was washed with saturated brine, dried and concentrated under reduced pressure to give 1-(2-trifluoromethyl-4-pyrimidinyl)piperazine (680 mg) as a brown solid.(3) In the same manner as in Example 29(1) and using the title compound (0.832 g) of Reference Example 3 and the above-mentioned compound (0.676 g), 3-{(2S,4S)-1-tert-butoxycarbonyl-4-[4-(2-trifluoromethyl-4-pyrimidinyl)-1-piperazinyl]-2-pyrrolizinylcarbonyl}-1,3-thiazolidine (1.28 g) was obtained as a pale-brown solid.(4) The above-mentioned compound (1.27 g) was dissolved in ethanol (3 mL) and a 4.1 mol/L hydrochloric acid-ethanol solution (3 mL) was added. The mixture was stirred at room temperature for 13 hr. The reaction solution was concentrated under reduced pressure, and ethyl acetate was added to the residue. The precipitate was collected by filtration to give the title compound (1.02 g) as a white solid.1H-NMR(DMSO-d6) delta 2.15-2.33(1H,m), 2.90-4.05(16H,m), 4.45-4.78(3H,m), 7.24(1H,d,J=6.3Hz), 8.45(1H,d,J=6.3Hz), 9.12(1H,brs), 10.83(1H,brs), 12.7(1H,brs).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1514-96-1, 4-Chloro-2-(trifluoromethyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Mitsubishi Pharma Corporation; EP1426366; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 767-15-7 ,Some common heterocyclic compound, 767-15-7, 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 stirred solution of 2-fluoro-5-nitrotoluene (2 g, 12.903 mmol) in DMF (15 ml) was added 2- amino-3,5-dimethylpyrimidine (1.58 g, 12.90 mmol) and Cs2CO3 (6.2 g, 25.806 mmol) in a flask at room temperature and stirred for 16 h at 80 ¡ãC. Reaction mixture was monitored by TLC (50percent Ethyl acetate/Pet ether). After completion of the reaction, the reaction was allowed to room temperature and poured into ice water mixture and extracted with AcOEt (2 X 100 ml). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to give crude 4-methyl-N-(2-methyl-4-nitrophenyl) pyrimidin-2-amine (2.2 g). The crude product was used for next step without purification. Mass: (ES+) C13H14N4O2 required 258.1; found 259.1 [M+H], HPLC/MS method 2.

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. 767-15-7, 2-Amino-4,6-dimethylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GENOSCIENCE PHARMA; BRUN, Sonia; BERET, Antoine; BASSISSI, Firas; HALFON, Philippe; COURCAMBECK, Jerome; (275 pag.)WO2017/191599; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 22536-65-8, 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.22536-65-8, name is 2-Chloro-5-methoxypyrimidine, molecular formula is C5H5ClN2O, molecular weight is 144.56, as common compound, the synthetic route is as follows.

To a suspensiOn of 6-(3-fluoro-4-(piperidin-4-yl)phenyl)-2H-benzo[d][l,3]oxathiole 3,3- dioxide (290 mg, 0.7 mmol) and 2-chloro-5-methoxypyrimidine (115 mg, 0.85 mmol) in acetonitrile (20 mL) was added triethylamine (63 mg, 0.6 mmol) and the reaction mixture was heated to reflux for 6 hours. Upon completion, the reaction mixture was cooled to ambient temperature. A white precipitate was formed which was filtered which was filtered off, washed with cold water and hexanes and then the crude product was purified by column chromatography on silica gel, eluting with dichloromethane to give the title compound (76 mg, 22 percent) as a white powder.

The chemical industry reduces the impact on the environment during synthesis 22536-65-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Peu Lama Na Perm Syutikeolseu In Keu .; Man Su-reu-ta-rek-su-ha-il; Cha Pi-beu-mi-ka-il; Yu Din-mi-ka-il; Ge Jen-cheu-be-i-yu-ri; Ni Ki-tin-al-rek-san-deu-reu; (190 pag.)KR2019/15535; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 61727-34-2, 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 61727-34-2, name is Ethyl 2-(4-chloro-2-(methylthio)pyrimidin-5-yl)acetate. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 121 (2.6 g, 10 mrnoi) in EtOH (20 mL) is added zinc powder (2.6 g, 40 mrnol) and HOAc (2 mL). After stirring at room temperature overnight, the mixture is filtered and concentrated. The residue is dissolved in EA (30 mL), washed with brine, diied over anhydrous sodium sulfate, filtered, and concentrated to give 122 as a yellow oil (1,2 g, 56% yield). (MS: [M+H] 213.1)

According to the analysis of related databases, 61727-34-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IMMUNE SENSOR, LLC; THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; ZHONG, Boyu; SUN, Lijun; SHI, Heping; LI, Jing; CHEN, Chuo; CHEN, Zhijian; (270 pag.)WO2017/176812; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 90349-23-8, 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.90349-23-8, name is 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid, molecular formula is C9H9N3O2, molecular weight is 191.19, as common compound, the synthetic route is as follows.

A mixture of 5,7-dimethylpyrazolo[l,5-a]pyrimidine-3-carboxylic acid 2 (50 mg, 0.26 mmol), 4-methyl-3-(l,3-oxazol-2-yl)aniline (55 mg, 0.314 mmol) and HATU (57 mg, 0.39 mmol) in DMF/NMM (1 mL/0.1 mL) was stirred at room temperature for 12 hours. The reaction mixture was added with water (2 mL), stirred at room temperature for 0.5 hour and then filtered. The resulting solid was washed with water (1 mL), DCM (2 mL), Et20 (2 mL) and dried in vacuo to give the title compound (62 mg, 68.0%) as a white solid.XH NMR (400 MHz, DMSO) delta 10.22 (s, 1H), 8.64 (s, 1H), 8.45 (s, 1H), 8.27(s, 1H), 7.66 (s, 1H), 7.45 (m, 1H), 7.36-7.39 (m, 1H), 7.21 (s, 1H), 2.77 (s, 3H), 2.72 (s, 3H), 2.61 (s, 3H). ES-MS m/z: 348.1 [M+H]+. LC-MS Purity (254 nm): > 99%; tR= 1.91 min.

Statistics shows that 90349-23-8 is playing an increasingly important role. we look forward to future research findings about 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid.

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: 56844-40-7, 6-Bromothieno[2,3-d]pyrimidin-4(3H)-one, 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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

1 L cc. sulfuric acid was cooled with ice-water bath and 72.0 g potassium iodide (0.434mol) was added in portions during 15 minutes and then 32.4 g sodium periodate (0.151mol) during a 10 minutes period. The resulting mixture was stirred at room temperature for30 minutes then 80.0 g 6-bromo-3H-thieno[2,3-djpyrimidin-4-one (0.346 mol) was addedto the mixture in portions in 30 minutes while the internal temperature was kept between -21 C and -19 C. The reaction mixture was stirred at -20 C for 1,5 hours. lee (3 kg) was added to the suspension then the precipitate was filtered off, washed with water (3×500 mL), finally with diethyl ether (3×200 mL) and air dried to give the product as a tan crystalline solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,56844-40-7, 6-Bromothieno[2,3-d]pyrimidin-4(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; LES LABORATOIRES SERVIER; VERNALIS (R&D) LIMITED; KOTSCHY, Andras; SZLAVIK, Zoltan; CSEKEI, Marton; PACZAL, Attila; SZABO, Zoltan; SIPOS, Szabolcs; RADICS, Gabor; PROSZENYAK, Agnes; BALINT, Balazs; BRUNO, Alain; GENESTE, Olivier; DAVIDSON, James Edward Paul; MURRAY, James Brooke; CHEN, I-Jen; PERRON-SIERRA, Francoise; WO2015/97123; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 34289-60-6 , The common heterocyclic compound, 34289-60-6, name is 4,6-Dimethylpyrimidin-2-ol hydrochloride, molecular formula is C6H9ClN2O, 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: An equimolar mixture (0.0125 mol) of 2-hydroxypyrimidines 1-2 and a corresponding arylcarboxaldehyde in 80 ml of ethanol was stirred for about 15min and then treated with 2.5 mL of HCl (cc). The obtained reaction mixture was heated under reflux for 6 h togive the corresponding hydrochlorides as red solids, which were then neutralized by 10% aqueous-alcoholic solution of carbonate of potassium. The resulting products (yellow solids) were filtered off, washed by hotethanol and dried in the air.

The synthetic route of 34289-60-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Komissarova, Ekaterina A.; Sosnin, Evgenii; Shklyaeva, Elena V.; Osorgin, Irina V.; Abashev, Georgii G.; Arkivoc; vol. 2017; 3; (2017); p. 105 – 120;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1005-37-4, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 1005-37-4 as follows.

-Chloro-N4-methyl-pyrimidine-2,4-diamine (50 mg; 0,3 mmol) was dissolved in 1-Butanol extra pure NF (4 ml) and N-Ethyldiisopropylamine for synthesis (0,13 ml) was added followed by 2-[(2-methoxyphenyl)methyl]pyrrolidine (66 mg; 0,33 mmol). The reaction was stirred at 160C over night during which the color changed into a yellow solution. (0644) The mixture was evaporated under vacuum. The residue was extracted with ethyl acetate/water. The organic layer was dried over sodium sulphate, filtered and evaporated under vacuum. The residue was suspended in diethylether and filtered by suction giving 55 mg of the product as brown solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1005-37-4, its application will become more common.

Reference:
Patent; MERCK PATENT GMBH; HEINRICH, Timo; PEHL, Ulrich; (206 pag.)WO2016/128140; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 24391-41-1 ,Some common heterocyclic compound, 24391-41-1, molecular formula is C7H3ClN4, 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.

A mixture of 2c (0.59 mmol), 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (105 mg, 0.59 mmol) and TEA (0.41 mL, 2.95 mmol) in n-BuOH (9 mL) was heated at 130 C for 2 hours. After concentration, the residue was washed with water and dried, then purified by preparative TLC and Compound 59 as a pale yellow solid was obtained (160mg, yield: 63%). MS (m/z): 431.1 (M+H)+. 1H NMR (400 MHz, DMSO-d6) delta: 12.94 (s, 1H), 8.32 (m, 2H), 7.67 (s, 1H), 6.67 (s, 1H), 6.45 (t, J = 55.2 Hz, 1H), 5.87 (m, 1H), 4.67 (m, 2H), 4.52 – 4.26 (m, 2H), 3.01 (m, 1H), 2.72 (m, 1H).

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. 24391-41-1, 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-Guo; DAI, Guangxiu; XIAO, Kun; JIA, Hong; VENABLE, Jennifer Diane; BEMBENEK, Scott Damian; WO2014/15523; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia