Pyrimidines

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;,
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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;,
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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;,
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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;,
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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;,
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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;,
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Application of 161489-05-0, 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 161489-05-0 as follows.

To a microwave vial charged with N-(4-fluoro-5-(l, 2,3,6- tetrahydropyridin-4-yl)-2-((3S,5R)-3,4,5-trimethylpiperazin-1-yl)phenyl)-6-oxo-4- (trifluoromethyl)-l,6-dihydropyridine-3-carboxamide (25.5 mg, 0.050 mmol) and 4- iodo-6-methoxy pyrimidine (13.64 mg, 0.058 mmol) in ethanol (3 ml) at RT, was added N,N-diisopropylethylamine (0.018 ml, 0.100 mmol) . The mixture was heated at 130 C for 3 h. The reaction was worked up and the product was purified by sgc to afford the title compound (19 mg, 58 % yield). 1H NMR (500 MHz, METHANOL- d4) delta = 8.26 – 8.21 (m, 1H), 7.98 – 7.93 (m, 1H), 7.85 – 7.76 (m, 1H), 6.99 – 6.94 (m, 1H), 6.94 – 6.90 (m, 1H), 6.12 (br s, 1H), 6.04 (s, 1H), 4.26 – 4.16 (m, 2H), 4.00 – 3.88 (m, 5H), 3.03 (br d, J=11.0 Hz, 2H), 2.65 – 2.52 (m, 6H), 2.38 (s, 3H), 1.19 – 1.15 (m,6H); LCMS [M+H]+ 616.6

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,161489-05-0, its application will become more common.

Reference:
Patent; ONTARIO INSTITUTE FOR CANCER RESEARCH (OICR); AL-AWAR, Rima; ZEPEDA-VELAZQUEZ, Carlos Armando; PODA, Gennady; ISAAC, Methvin; UEHLING, David; WILSON, Brian; JOSEPH, Babu; LIU, Yong; SUBRAMANIAN, Pandiaraju; MAMAI, Ahmed; PRAKESCH, Michael; STILLE, Julia Kathleen; (1053 pag.)WO2017/147700; (2017); A1;,
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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.109-12-6, name is Pyrimidin-2-amine, molecular formula is C4H5N3, molecular weight is 95.1, as common compound, the synthetic route is as follows.Recommanded Product: 109-12-6

General procedure: To a solution of Cu(OAc)2 (0.025 mmol, 0.0046 g) and potassium tert-butoxide (0.175 g, 2.5 mmol) in anhydrous dioxane (3 mL), the corresponding amine 1 (2.5 mmol) or the triphenylphosphoranylidenaniline 18 (2.5 mmol) and the correspondent alcohol 2 or 4 (3.75 mmol) were added successively under inert argon atmosphere. After 2 or 5 days of reaction at 130 C (see Table 2 and Scheme 2), the resulting mixture was hydrolyzed with a saturated solution of ammonium chloride (10 mL). The mixture was extracted with AcOEt (3¡Á10 mL) and washed with brine (10 mL), after drying with anhydrous MgSO4, was filtered on Celite and the solvents were removed under low pressure(15-18 Torr). The resulting mixture was purified by column chromatography (if needed).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,109-12-6, Pyrimidin-2-amine, and friends who are interested can also refer to it.

Reference:
Article; Martinez-Asencio, Ana; Ramon, Diego J.; Yus, Miguel; Tetrahedron; vol. 67; 17; (2011); p. 3140 – 3149;,
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Electric Literature of 88474-31-1 ,Some common heterocyclic compound, 88474-31-1, molecular formula is C6H8ClN3O, 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-amino-4-methoxy-6-chloro-3-methyl-pyrimidine (2.0grams, 11.5mmol) and N-acetylimidazolidinone (2.0 grams, 11,5mmol) were dissolved in anhydrous DMSO and anhydrous sodium carbonate (3.75 grams, 35.4mmol, 2.0 equivalents) was added. The reaction flask was cooled in ice-salt-acetone mixture and POCl3 was added dropwise in 1 hour keeping temperature below 5C. After the addition the ice bath was removed and the flask was stirred at 58-60C under nitrogen for 2 days. A small sample was taken and analysed by HPLC. There was no starting material and the product was formed. The anhydrous Na2CO3 neutralized the HCl gas in situ as it formed. Workup: The reaction mixture was quenched by slowly pouring in crushed ice. The product precipitated and the product was filtered and dried under vacuum. Without any further purification the product was used in the next step to generate crude moxonidine. Yield: 2.64 grams. Mass spec.: 283 (m+)

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. 88474-31-1, 4-Chloro-6-methoxy-2-methylpyrimidin-5-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Abbott Healthcare Products B.V.; ABBOTT LABORATORIES; ACQUASALIENTE, Maurizio; LAGERWEIJ, Gert; DESHPANDE, Mahendra; SHAH, Rajendra; EP2829540; (2015); A1;,
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Electric Literature of 89487-99-0 , The common heterocyclic compound, 89487-99-0, name is 4-Hydroxy-2-(methylthio)pyrimidine-5-carbonitrile, molecular formula is C6H5N3OS, 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 cooled solution of 4-hydroxy-2-(methylthio)pyrimidine-5-carbonitrile (8) (10.8 g, 65 mmol) in toluene (150 ml), phosphorus oxychloride (23.8 ml, 260 mmol) was slowly added. The reaction mixture was stirred at 110 C for 6 h. After evaporation of the organic solvent, the residue was cooled to room temperature and added a lot of ice water. At this time, a brown solid was formed and collected by filtration. The crude product was dried in a vacuum oven to give 4-chloro-2-(methylthio)pyrimidine -5-carbonitrile 9(6.8 g). This product was taken up for the next step without any purification. Yield: 58%; Purity: 90%; LC-MS m/z: 186.0 [M + H]+.

The synthetic route of 89487-99-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Ling-Ling; Li, Guo-Bo; Yan, Heng-Xiu; Sun, Qi-Zheng; Ma, Shuang; Ji, Pan; Wang, Ze-Rong; Feng, Shan; Zou, Jun; Yang, Sheng-Yong; European Journal of Medicinal Chemistry; vol. 56; (2012); p. 30 – 38;,
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