Pyrimidines

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. 52602-68-3, name is 6-Chloro-N4-methyl-4,5-pyrimidinediamine. A new synthetic method of this compound is introduced below., Recommanded Product: 6-Chloro-N4-methyl-4,5-pyrimidinediamine

General procedure: A mixture of the 4,5-diamino-6-chloro-N4-methylpyrimidine (6, 1mmol), the appropriate arylaldehyde (1.2mmol), acetic acid (2.3mmol) in methanol (4.3mL) was stirred at room temperature for 16h. The reaction mixture was concentrated to dryness under reduced pressure. The residue was azeotropically distilled with toluene (2¡Á4mL) and used directly in the next step. To the suspension in ethanol (6mL) of the crude imine, a solution of anhydrous FeCl3 (1mmol) in ethanol (3mL) was added. The mixture was stirred at 80C for the time stated below for each product. The solvent was removed and the 8-aryl-6-chloro-9-methyl-9H-purines 26-36 were obtained as pure compounds after silica gel flash chromatography and crystallization.

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, 52602-68-3, 6-Chloro-N4-methyl-4,5-pyrimidinediamine.

Reference:
Article; Lambertucci, Catia; Marucci, Gabriella; Dal Ben, Diego; Buccioni, Michela; Spinaci, Andrea; Kachler, Sonja; Klotz, Karl-Norbert; Volpini, Rosaria; European Journal of Medicinal Chemistry; vol. 151; (2018); p. 199 – 213;,
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Pyrimidine – Wikipedia

Reference of 2565-47-1, 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.2565-47-1, name is 1-Methylpyrimidine-2,4,6(1H,3H,5H)-trione, molecular formula is C5H6N2O3, molecular weight is 142.1127, as common compound, the synthetic route is as follows.

Phosphoryl chloride (55 ml) is carefully added to barbituric acid (10 g, 78.1 mmol) at 0 C. Water (1.7 ml) is then added dropwise such that the temperature does not exceed 5 C. The mixture is boiled under reflux for 5 h and, after it has cooled down, poured onto ice. The product is extracted with ethyl acetate (3¡Á100 ml) and dried (Na2 SO4). The mixture is filtered and the solvent is distilled off in vacuo.

The chemical industry reduces the impact on the environment during synthesis 2565-47-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Aventis Pharma Deutschland GmbH; US2004/242583; (2004); A1;,
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Adding a certain compound to certain chemical reactions, such as: 16019-33-3, 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde, 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-(4,6-Dichloropyrimidin-5-yl)acetaldehyde, blongs to pyrimidines compound. name: 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde

Example 12Preparation of Compound 9Step 1 – Synthesis of compound 12A; 2-Fluoro-4-sulfonylmethyl aniline (0.104 g, 0.55 mmol) was cooled to -15 0C, then was diluted with TFA (0.55 mL, 7.4 mmol) and the resulting solution was allowed to stir for 30 minutes. Sodium triacetoxyborohydride (2.75 mmol) was then added portionwise and the resulting reaction was allowed to stir for an additional 30 minutes. To this reaction mixture was added a solution of compound 3 (0.1 g, 0.523 mmol) in dichloromethane (1.0 mL) and the resulting reaction was allowed to stir for 15 hours. The organic layer was collected and extracted with dichloromethane, and the dichloromethane was then washed with saturated aqueous sodium bicarbonate solution, dried over MgSO4, filtered and concentrated in vacuo. The residue obtained was purified using flash column chromatography on silica gel (30% acetone / hexanes) to provide compound 12 A (0.133 g, 69%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16019-33-3, 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; SCHERING CORPORATION; NEELAMKAVIL, Santhosh, Francis; BOYLE, Craig, D.; CHACKALAMANNIL, Samuel; GREENLEE, William, J.; WO2010/9195; (2010); A1;,
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Pyrimidine – Wikipedia

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. 10320-42-0, name is 2-Chloro-5-nitropyrimidine, molecular formula is C4H2ClN3O2, 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. Formula: C4H2ClN3O2

General procedure: A mixture of compound 8 (10.0 g, 23.4 mmol) and 2-chloro-5-nitropyrimidine (3.90 g, 24.5 mmol) in THF (80 mL) was refluxed overnight. After removal of the solvent, the residue was purified by silica gel column chromatography (hexane/AcOEt = 70:30 to 0:100) to give the title compound (11.0 g, 20.0 mmol, 98percent) as a yellow solid.

With the rapid development of chemical substances, we look forward to future research findings about 10320-42-0.

Reference:
Article; Sato, Kenjiro; Takahagi, Hiroki; Kubo, Osamu; Hidaka, Kousuke; Yoshikawa, Takeshi; Kamaura, Masahiro; Nakakariya, Masanori; Amano, Nobuyuki; Adachi, Ryutaro; Maki, Toshiyuki; Take, Kazumi; Takekawa, Shiro; Kitazaki, Tomoyuki; Maekawa, Tsuyoshi; Bioorganic and Medicinal Chemistry; vol. 23; 15; (2015); p. 4544 – 4560;,
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Adding a certain compound to certain chemical reactions, such as: 10320-42-0, 2-Chloro-5-nitropyrimidine, 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, Application In Synthesis of 2-Chloro-5-nitropyrimidine, blongs to pyrimidines compound. Application In Synthesis of 2-Chloro-5-nitropyrimidine

a dry 50 ml reaction flask was vacuumed three times with nitrogen, then added 2-tert-butylphenol (150 mg, 1.0 mmol, 1.0 equiv) to the reaction flask, and added 3.0 ml of dried THF. Stir to 2-tert-butylphenol to dissolve, then add NaH (28.8 mg, 1.2 mmol, 1.2 equiv, sodium hydride content 60percent suspended in mineral oil) to the reaction flask under ice bath, under ice bath The reaction was carried out for 30 min; then 2-chloro-5-nitropyrimidine (0.1593 g, 1.0 mmol, 1.0 equiv) was added to the reaction flask. The entire mixture was slowly raised to a temperature of 50 ¡ã C for 12 hours. The reaction was monitored by TLC, and the reaction was stopped if it was detected that all of the phenol was completely reacted. The experimental treatment was to drain the solution in the reaction; dissolve the solute in the reaction flask with ethyl acetate, transfer it to a 100 ml round bottom flask, and add 3 ml (200-300 mesh) of silica gel to the round bottom flask. Dry (petroleum ether and ethyl acetate) over silica gel on the column.The intermediate product was white crystals of 2-(2-(tert-butyl)phenoxy)-5-nitropyrimidine (189 mg, 87percent yield).

The synthetic route of 10320-42-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jinan University; Feng Pengju; Chen Tianfeng; Chen Junfeng; Huang Yifeng; (19 pag.)CN108164397; (2018); A;,
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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.5018-38-2, name is 4,6-Dichloro-5-methoxypyrimidine, molecular formula is C5H4Cl2N2O, molecular weight is 179, as common compound, the synthetic route is as follows.Quality Control of 4,6-Dichloro-5-methoxypyrimidine

General procedure: To a solution of amine (320 mg, 0.8 mmol) in N-methyl-2-pyrrolidone (6 mL) was added diisopropylethylamine (270 mg, 2 mmol). The solution was stirred for 5 mm at room temperature at which time 4,6-dichloro-5-methoxypyrimidine (150 mg, 0.8 mmol) was added. The reaction mixture was stirred at 80C overnight then allowed to cool to room temperature. Water was added and the resulting mixture was extracted with methyl tert-butylether (3x). The combinedorganic layers were washed with water, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by HPLC to provide 139mg (0.3 mmol, 37%) of the light yellow oily product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5018-38-2, 4,6-Dichloro-5-methoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BASF SE; BASF SCHWEIZ AG; GRAMMENOS, Wassilios; CRAIG, Ian Robert; BOUDET, Nadege; MUeLLER, Bernd; DIETZ, Jochen; LAUTERWASSER, Erica May Wilson; LOHMANN, Jan Klaas; MONTAG, Jurith; WO2013/135672; (2013); A1;,
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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. 3921-01-5, name is 2,4-Dibromopyrimidine, the common compound, a new synthetic route is introduced below. Safety of 2,4-Dibromopyrimidine

2,4-dibromopyrimidine (438.4mg, 1.84mmol) and potassium carbonate (1.27g, 9.21mmol) in tetrahydrofuran (10mL) were added together and stirred at room temperature for 5min. Morpholine (174.8muL, 2.03mmol) was then added dropwise and the solution continued to stir at room temperature for 5h. The reaction mixture was filtered and the filtrate was collected and then concentrated under reduced pressure. The products were purified by silica column chromatography in hexanes and ethyl acetate to afford 28a and 28b in 19% and 66% yields, respectively. (0070) 4-(4-bromopyrimidin-2-yl)morpholine (28a). (White solid, Yield: 19%). 1H NMR (500MHz, CDCl3) delta ppm 3.74-3.77 (m, 4H) 3.79-3.83 (m, 4H) 6.70 (d, J=4.88Hz, 1H) 8.05 (d, J=4.88Hz, 1H). LCMS found 246.0, [M+H]+. (0071) 4-(2-bromopyrimidin-4-yl)morpholine (28b). (White solid, Yield: 66%) 1H NMR (500MHz, CDCl3) delta ppm 3.66 (br. s., 4H) 3.76-3.83 (m, 4H) 6.43 (d, J=6.35Hz, 1H) 8.02 (d, J=6.35Hz, 1H). LCMS found 246.0, [M+H]+.

The synthetic route of 3921-01-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Woodring, Jennifer L.; Bachovchin, Kelly A.; Brady, Kimberly G.; Gallerstein, Mitchell F.; Erath, Jessey; Tanghe, Scott; Leed, Susan E.; Rodriguez, Ana; Mensa-Wilmot, Kojo; Sciotti, Richard J.; Pollastri, Michael P.; European Journal of Medicinal Chemistry; vol. 141; (2017); p. 446 – 459;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1401162-80-8, Methyl 4-(4-fluorophenyl)pyrimidine-2-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, 1401162-80-8, blongs to pyrimidines compound. Recommanded Product: 1401162-80-8

Example 32B4-(4-fluorophenyl)pyrimidine-2-carbaldehydeDIBAL-H (3.62 mL, 3.62 mmol, 1.0 M in toluene) was slowly added to a suspension of Example 32A (700 mg, 3.01 mmol) in toluene (30 mL) at -75 C. After 2 hours, DIBAL-H (1.507 mL, 1.507 mmol, 1.0 M in toluene) was added to the reaction mixture and warmed slowly to ambient temperature overnight. The reaction was a clear orange-red solution and the methyl ester was consumed, yielding a mixture of aldehyde and alcohol. Additional DIBAL-H (1.507 mL, 1.507 mmol, 1.0 M in toluene) was added at ambient temperature. After 4 hours, the reaction was quenched with 5% acetic acid in water (200 mL), extracted twice with EtOAc (200 mL), washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was chromatographed on a Grace Reveleris 12 g column, eluted with 0-60% EtOAc in dichloromethane (25 mL/min) to provide the title compound (62 mg, 0.307 mmol, 10.17% yield) as an off-white solid. MS (ESI+) m/z 234.8 (M+H-MeOH); 1H NMR (300 MHz, DMSO-d6) delta 10.04 (s, 1H), 9.12 (d, J=5.3, 1H), 8.38 (dd, J=9.0, 5.5, 2H), 8.32 (d, J=5.4, 1H), 7.45 (t, J=8.9, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1401162-80-8, its application will become more common.

Reference:
Patent; ABBOTT LABORATORIES; US2012/245124; (2012); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 73418-88-9, Methyl 5-aminopyrimidine-2-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, Application In Synthesis of Methyl 5-aminopyrimidine-2-carboxylate, blongs to pyrimidines compound. Application In Synthesis of Methyl 5-aminopyrimidine-2-carboxylate

Methyl 5-aminopyrimidine-2-carboxylate (0.065 g, 0.425 mmol) and pyridine (0.172 mL, 2.123 mmol) were dissolved in DCM (2 mL). To this solution was added Intermediate I-141A (0.072 g, 0.212 mmol) as a solution in DCM (1 mL). The reactionmixture was allowed to stir for lh. The reaction mixture was concentrated under reducedpressure. Purified on ISCO using 0-100% EtOAc in hexanes to yield Intermediate 1-141(0.066 g, 0.145 mmol, 68.2 % yield) as a white solid. ?H NMR (400MHz, CDC13) 9.04(s, 2H), 7.87 (d, J=9.7 Hz, 1H), 6.94 (s, 1H), 5.56 (dd, J=6.5, 2.8 Hz, 1H), 5.38-5.17 (m,1H), 4.09 (s, 3H), 1.47 (d, J=6.4 Hz, 6H). LC-MS: method H, RT = 0.93 mm, MS (ESI)m/z: 456.0 (M+H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,73418-88-9, Methyl 5-aminopyrimidine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; BATES, J. Alex; HALPERN, Oz Scott; REZNIK, Samuel Kaye; RICHTER, Jeremy M.; (1137 pag.)WO2018/13774; (2018); A1;,
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Electric Literature of 2435-50-9, 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. 2435-50-9, name is Pyrimidine-4-carbaldehyde. A new synthetic method of this compound is introduced below.

General procedure: A suspension of methyl 2-(2-aminoethyl)-1 ,3-thiazole-4-carboxylate (5) (1.96 g, 10.52 mmol), 1 H- benzimidazole-2-carbaldehyde (2.31 g, 15.79 mmol) and DIPEA (1.83 ml, 10.52 mmol) in MeOH (100 ml) was stirred at room temperature for 12 h. The reaction mixture was cooled to 0C, NaBH4 (0.597 g, 15.79 mmol) was added and the mixture stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo and the residue dissolved in EtOAc (100 ml) and washed with saturated NC03 (2 x 50 ml). The combined aqueous layers were extracted with EtOAc (3 x 50 ml) and the combined organic layers dried (MgS04), filtered and evaporated in vacuo. Purification by flash column chromatography (KP- NH, eluting with a gradient of 0-10% MeOH / DCM) afforded the title compound (1.4 g, 38%, 90% purity) as a tan solid. 1 H-NMR (Methanol-d4, 250 MHz): d[ppm]= 8.27 (s, 1 H), 7.60 – 7.49 (m, 2H), 7.29 – 7.17 (m, 2H), 4.09 (s, 2H), 3.92 (s, 3H), 3.26 (t, J = 6.3 Hz, 2H), 3.10 (t, J = 6.8 Hz, 2H) HPLCMS (Method A): [m/z]: 317 [M+H]+In a similar fashion to general procedure 3, 2-(2-aminoethyl)-N-benzyl-1 ,3-thiazole-4-carboxamide (104) (150 mg, 0.574 mmol), pyrimidine-4-carbaldehyde (61 mg , 0.564 mmol), TEA (0.79 ml, 6 mmol) in MeOH (2 ml) at room temperature for 6 h, followed by addition of NaBH; (32 mg, 0.846 mmol) gave the title compound (150 mg, 75%) as an brown oil after purification by flash column chromatography (eluting with a gradient of 5% MeOH in DCM). 1 H-NMR (CDCb, 400 MHz): d[ppm]= 9.05 (d, J = 1.3 Hz, 1 H), 8.63 (d, J = 5.2 Hz, 1 H), 8.04 (s, 1 H), 7.69 (s, 1 H), 7.39 – 7.27 (m, 6H), 4.66 (d, J = 6.1 Hz, 2H), 3.94 (s, 2H), 3.20 (t, J = 6.3 Hz, 2H), 3.09 (t, J = 6.6 Hz, 2H), HPLCMS (Method L): [m/z]: 354.0 [M+H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2435-50-9, Pyrimidine-4-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; VIFOR (INTERNATIONAL) AG; DUeRRENBERGER, Franz; BUHR, Wilm; BURCKHARDT, Susanna; BURGERT, Michael; KALOGERAKIS, Aris; REIM, Stefan; MANOLOVA, Vania; BOYCE, Susan; YARNOLD, Christopher John; PENA, Paula; SHEPHERD, Jon; LECCI, Cristina; JARJES-PIKE, Richard; SCOTT, John; (416 pag.)WO2017/68089; (2017); A2;,
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