Pyrimidines

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. 25193-95-7, name is 5-(Hydroxymethyl)pyrimidine, the common compound, a new synthetic route is introduced below. category: pyrimidines

General procedure: Glovebox Procedure (General Procedure 1): Inside an argonfilled glovebox (O2 levels between 35.0 and 55.0 ppm, H2O levels unknown), to an oven dried 10-mL screw cap vial equipped with a Teflon-coated magnetic stir bar were added Ru-MACHO (1.2 mg, 2.00 mmol), KOH (1.7 mg, 30.0 mmol), and the appropriate phosphinic amide (0.200 mmol) in that order. Subsequently, toluene (0.7 mL) was added via micropipette, with care taken to ensure that solids on the wall were washed to the bottom of the vial. Next, the appropriate alcohol (0.240 mmol) was added either as a solid or via micropipette for liquid substrates. The reaction was sealed tightly with a non-puncturable cap and was further sealed by placing a piece of electrical tape around the cap and top of vial. Schlenk Line Procedure (General Procedure 2): To a flame-dried vial were quickly added Ru-MACHO (1.2 mg, 2.00 mmol) and KOH (1.7 mg, 30.0 mmol) (stored under Ar) (addition time 1 min), and the reaction vial was left open under a steady flow of nitrogen (applied via a needle placed at the top of the vial). Next, the appropriate phosphinic amide (0.200 mmol) was added, followed by the addition of toluene (0.7 mL) from a standard Solvent Purification System (SPS). Lastly, the appropriate alcohol (0.240 mmol) was added either as a solid or via micropipette for liquid substrates. The nitrogen line was removed, and the vial was then quickly and tightly sealed with a non-puncturable cap and further sealed by placing a piece of electrical tape around the cap and top of the vial. After the differing series of operations described above, General Procedures 1 and 2 then followed then same protocol. The reaction vessel was placed in a preheated oil bath at 110e140 C with a stirring rate of 500 rpm. As the reaction was proceeding, the vessel was periodically visually monitored. If large amounts of solid were found to have accumulated on the wall, the vial was briefly removed from the oil bath and shaken to wash the solids back to the bottom of the vial. After 16 h, the vial was removed from the oil bath and allowed to cool to room temperature. Methanol (1 mL) was added to dissolve all solids, and the solvent removed in vacuo. The solid was redissolved in methanol (1 mL), and the solution was filtered through a 40-mm syringe filter. Samples were then purified by reverse-phase HPLC or recrystallized from hot benzene. In the case of HPLC purification, the fractions were combined, frozen in liquid N2, and lyophilized to sublime the solvent.

The synthetic route of 25193-95-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jankins, Tanner C.; Qin, Zi-Yang; Engle, Keary M.; Tetrahedron; vol. 75; 24; (2019); p. 3272 – 3281;,
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Application of 1450-85-7 ,Some common heterocyclic compound, 1450-85-7, molecular formula is C4H4N2S, 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: Potassium tetrachloridopalladate(II) was prepared as described previously [11]. The complexes were prepared by adding 2 equivalents of potassium cyanide in 10 ml water to a solution of K2[PdCl2](0.326 g) in 15 ml of water followed by the addition of 2 equivalents of thioamides in 15 ml methanol after 15 min stirring. On addition of KCN a light yellow turbid solution was obtained, which turned to brown or red clear solution on addition of thiones (Caution: Potassium cyanide is extremely dangerous and must be handled with care). After stirring the solutions to 1 h, their colors changed to yellow or orange red. The solutions were filtrated and were kept at room temperature for three to five days. The solid products obtained were washed with methanol and air dried. The experimental yield of the products was around 60-70%. The elemental analyses and melting points (m.p) of the complexes are given in Table 1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1450-85-7, its application will become more common.

Reference:
Article; Ahmad, Saeed; Nadeem, Shafqat; Anwar, Aneela; Hameed, Abdul; Tirmizi, Syed Ahmed; Zierkiewicz, Wiktor; Abbas, Azhar; Isab, Anvarhusein A.; Alotaibi, Mshari A.; Journal of Molecular Structure; vol. 1141; (2017); p. 204 – 212;,
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Reference of 1032452-86-0, 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.1032452-86-0, name is 3-(2-Chloropyrimidin-4-yl)-1-methyl-1H-indole, molecular formula is C13H10ClN3, molecular weight is 243.69, as common compound, the synthetic route is as follows.

Compound 1-(7-amino-6-methoxy-3,4-dihydroquinolin-1(2H)-yl)prop-2-en-1-one (0.22 g, .95 mmol),3-(2-Chloropyrimidin-4-yl)-1-methyl-1H-indole (0.19 g, 0.79 mmol)And p-chlorobenzoic acid (0.16g, 0.95mmol)In a two-necked flask,The reaction was carried out by adding 1,4-dioxane (6 mL) and heating to 90C.Check the progress of the reaction through the TLC point plate,About 5 hours after the reaction is completed,After processing,To room temperature,Add 25% aqueous ammonia (0.2 mL) and water (0.97 mL) to quench,Desolvent,Purification by column chromatographyThe product was obtained (83 mg, yield 24.0%).

The chemical industry reduces the impact on the environment during synthesis 1032452-86-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Tianjin Binjiang Pharmaceutical Research And Development Co., Ltd.; Tian Hongqi; Huang Gongchao; Cheng Ying; (48 pag.)CN107793413; (2018); A;,
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Synthetic Route of 3764-01-0 ,Some common heterocyclic compound, 3764-01-0, molecular formula is C4HCl3N2, 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.

PREPARATION A-23 4-[2,6-Bis(morpholino)-4-pyrimidinyl]piperazine A solution of 160 g of morpholine in 1000 ml of methylene chloride is treated dropwise with 100 g of 2,4,6-trichloropyrimidine. The reaction is immersed in an ice water bath. After 1 h, 300 ml of pyridine is added. The reaction is stirred for two days and concentrated. The residue is partitioned between methylene chloride and aqueous sodium bicarbonate. The residue is chromatographed on silica gel (10percent ethyl acetate/hexane to 25percent to methylene chloride) to give 2,4-[bis-morpholino]-6-chloropyrimidine.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3764-01-0, its application will become more common.

Reference:
Patent; THE UPJOHN COMPANY; EP263213; (1988); A1;,
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Pyrimidine – Wikipedia

Reference of 591-55-9, 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.591-55-9, name is 5-Aminopyrimidine, molecular formula is C4H5N3, molecular weight is 95.1, as common compound, the synthetic route is as follows.

6-(4-Chloro-phenyl)-5-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid (prepared as described in WO 2012/032018, Example AE) was combined with DMF (30 ml) at RT, to give a colorless solution. Pyrimidin-5 -amine, TBTU and N-Ethyldiisopropylamine were added. The reaction mixture was stirred at RT for 15 h. The reaction mixture was poured into 150 mL ]0 and extracted with EtOAc (2 x 150 mL). The combined organic layers were washed with brine, dried over MgS04 and evaporated. The crude material was purified by flash chromatography (silica gel, 20g, 0% to 50% EtOAc in hexane). LC-MS (ESI) 409.068 (M+H)+.

Statistics shows that 591-55-9 is playing an increasingly important role. we look forward to future research findings about 5-Aminopyrimidine.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC; FORNONI, Alessia; (59 pag.)WO2020/21097; (2020); A1;,
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Pyrimidine – Wikipedia

Related Products of 33034-67-2, 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. 33034-67-2, name is 2-Chloro-4-(trifluoromethyl)pyrimidine. A new synthetic method of this compound is introduced below.

Step 3 : A solution of 2-chloro-4-(trifluoromethyl)pyrimidine (0.297 g, 1.626 mmol) in dioxane (4 ml) was added to 3-Bromo-5-(difluoromethyl)aniline (0.314 g, 1.414 mmol) followed by methanesulfonic acid (0.1 1 ml, 1.694 mmol) and the resulting solution was heated overnight to 100 °C. The reaction was diluted with water and extracted with EtOAc. The organic phase was washed with saturated sodium bicarbonate, water, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel (EtOAc/hexane=2/8) to afford N- [3-bromo-5-(difluoromethyl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine. MS ESI calc’d. for Ci2H7BrF5N3 [M + H]+ 368, 370, found 368, 370. lH NMR (500 MHz, CDCI3) delta 8.65 (d, J= 4.9, IH), 8.09 (s, IH), 7.97 (s, IH), 7.73 (s, IH), 7.27 (s, IH), 7.07 (d, J= 4.9, IH), 6.56 (t, J= 56.2, IH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,33034-67-2, 2-Chloro-4-(trifluoromethyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALTMAN, Michael, D.; CHILDERS, Kaleen Konrad; DI FRANCESCO, Maria Emilia; ELLIS, John Michael; FISCHER, Christian; GRIMM, Jonathan; HAIDLE, Andrew, M.; KATTAR, Solomon, D.; NORTHRUP, Alan, B.; OTTE, Ryan, D.; PETROCCHI, Alessia; SCHELL, Adam, J.; ZHOU, Hua; WO2012/154519; (2012); A1;,
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Related Products of 1088994-22-2 , The common heterocyclic compound, 1088994-22-2, name is 5-Methyl-2-(pyrimidin-2-yl)benzoicacid, molecular formula is C12H10N2O2, 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 15 N-ethyl-N-{2-[4-(5-fluoropyridin-2-yl)-1H-pyrazol-1-yl]ethyl}-5-methyl-2-(pyrimidin-2-yl)benzamide DIPEA (0.28 mL, 1.6 mmol) was added to a solution of the compound (0.15 g, 0.64 mmol) obtained in Reference Example 2 in CHCl3 (3 mL) at room temperature. 5-Methyl-2-(pyrimidin-2-yl)benzoic acid (0.18 g, 0.83 mmol) and propylphosphonic acid anhydride (cyclic trimer) (50% solution in EtOAc (approximately 1.7 mol/L), 1.1 mL, 1.9 mmol) were added to the reaction solution under cooling in ice water. The resultant mixture was stirred at room temperature for 1 hour and further stirred in an oil bath with a temperature of 50 C. for 3 hours. After standing to cool to room temperature, water was added thereto, followed by extraction with CHCl3. The organic layer was washed with brine. Then, the organic layer was dried over Na2SO4, and the desiccant was filtered off. Then, the solvent was distilled off under reduced pressure. The obtained residue was purified by column chromatography (KP-NH 28 g, hexane/EtOAc=70/30?0/100) and further purified by HPLC to obtain the title compound (0.069 g) (colorless amorphous). LCMS retention time 4.37 min. (Condition 1) MS (ESI pos.) m/z: 431 [M+H]+

The synthetic route of 1088994-22-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; Nozawa, Dai; Suzuki, Ryo; Futamura, Aya; Shimono, Rie; Abe, Masahito; Ohta, Hiroshi; Araki, Yuko; US2013/281465; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 1193-24-4, name is 4,6-Dihydroxypyrimidine. A new synthetic method of this compound is introduced below., Safety of 4,6-Dihydroxypyrimidine

General procedure: According to the conventional manufacturing method of the present inventors [16], under the condition containing two equivalents of triethylamine in dichloromethane at 25 , 4,6- dihydroxy-pyrimidine with 2 equivalents of Compound 2 by acylating a new and compounds 4, 6-pyrimidyl di (2-halo-benzoate) (compound 3) is prepared. After evaporation of dichloromethane, the mixture is dissolved in anhydrous THF, to remove the triethylamine hydrochloride by filtration. The concentrated residue was purified by short length silica gel (Davisil, pH = 7) was purified by column chromatography, or the Compound 3 is prepared by purification was recrystallized with 75% EtOAc / n- hexane

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, 1193-24-4, 4,6-Dihydroxypyrimidine.

Reference:
Patent; Duksung Women’s University Academic Cooperation; Lee, Jae In; Song, Yun jU; Choe, Jin Son; (12 pag.)KR2015/106483; (2015); A;,
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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. 10244-24-3, name is 4,4′-(6-Chloropyrimidine-2,4-diyl)dimorpholine, the common compound, a new synthetic route is introduced below. Quality Control of 4,4′-(6-Chloropyrimidine-2,4-diyl)dimorpholine

The 4,4 ‘ – (6-chloro-pyrimidine -2,4-diyl) two morpholine (5.0g, 17 . 6mmol), pinacone esterjoint boric acid (5.8g, 22 . 8mmol) and potassium acetate (2.59g, 26 . 4mmol) into acetonitrile (100 ml) in, under the protection of nitrogen by adding three ring hexyl phosphine (395 mg, 1 . 4mmol) and three (dibenzalacetone) palladium II (645 mg, 0 . 7mmol), the temperature is increased to 84 C reaction 3 hours, to take advantage of heat filtering, the filtrate after turns on lathe does adding toluene (30 ml) and petroleum ether (100 ml), stirring, precipitate, filtered, the filter cake is washed with petroleum ether washing, to obtain the title compound (3.8g, yield 57.4%).

The synthetic route of 10244-24-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong Xuanzhu Oharma Co., Ltd.; Wu, Yongjian; (47 pag.)CN105541792; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 271-70-5, Adding some certain compound to certain chemical reactions, such as: 271-70-5, name is 7H-Pyrrolo[2,3-d]pyrimidine,molecular formula is C6H5N3, 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 271-70-5.

7H-Pyrrolo[2,3-d]pyrimidine (6, 0.450 g, 3.78 mmol), (5-formyl-pyridin-2-yl)-(6-methoxy-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester (71, 1.43 g, 4.16 mmol), potassium hydroxide (0.689 g, 12.3 mmol) and 6.6 mL methanol were combined in a reaction vessel. The reaction mixture was allowed to stir at room temperature for 36 hours, then concentrated under vacuum to provide a thick brown slurry, which was combined with ethyl acetate and aqueous saturated sodium bicarbonate. The organic layer was dried with sodium sulfate, filtered and the filtrate adsorbed onto silica. This was purified by silica gel column chromatography, eluting with a gradient of 1-10% methanol in dichloromethane over 30 minutes. Appropriate fractions were combined and the solvents removed under vacuum to provide the desired compound (72, 380 mg). 1H NMR was consistent with the compound structure.

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. 271-70-5, 7H-Pyrrolo[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ibrahim, Prabha N.; Bremer, Ryan; Zhang, Jiazhong; Nespi, Marika; Cho, Hanna; US2009/286782; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia