Day: March 25, 2022

Electric Literature of 259809-79-5, 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. 259809-79-5, name is tert-Butyl 7,8-dihydro-2-(methylsulfonyl)pyrido[4,3-d]pyrimidine-6(5H)-carboxylate, molecular formula is C13H19N3O4S, 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.

[0164] Tert-butyl 2-(methylsulfonyl)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)- carboxylate (1 g, 3.195 mmol) was dissolved in was dissolved in 10 mL of ethanol followed by addition of cyclopropylamine (300mg, 5.263mmol). The mixture was stirred at 80 °C for 12 hours. The solvent was removed by vacuum, and the residue was purified by column chromatography (petroleum ethenEtOAc = 4:1) to give a white solid (460 mg, 50.4percent).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 259809-79-5, tert-Butyl 7,8-dihydro-2-(methylsulfonyl)pyrido[4,3-d]pyrimidine-6(5H)-carboxylate.

Reference:
Patent; ZHANG, Xiaohu; WO2014/113191; (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 37482-64-7, name is 2-Chloro-4-ethoxy-6-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 2-Chloro-4-ethoxy-6-methylpyrimidine

To a round bottom flask containing 600 mg (3.48 mmol) of 2-chloro-4-ethoxy-6-methylpyrimidine, 489 mg (5.22 mmol) of azetidine hydrochloride, 131 mg (0.69 mmol) of CuI, 164 mg (0.69 mmol) of 3,4,7,8-tetramethyl-1,10-phenanthroline and 2.83 g (8.70 mmol) of Cs2CO3 was added 15 mL of dry, degassed DMF. The reaction mixture was stirred at 50 C for 3 h. The cooled reaction mixture was filtered through Celite and the Celite pad was washed with portions of CH2Cl2. The combined organic phase was washed with water and then with brine, dried (MgSO4) and concentrated under diminished pressure. The residue was purified by flash chromatography on a silica gel column (15 * 3 cm). Elution with 19:1 hexane/EtOAc followed by 9:1 hexane/EtOAc afforded 18 as a colorless solid: yield 565 mg (84%); mp 42-43 C; silica gel TLC Rf 0.29 (3:2 hexane/EtOAc); 1H NMR (CDCl3) delta 1.24 (t, 3H, J = 7.2 Hz), 2.16 (s, 3H), 2.20 (quint, 2H, J = 7.6 Hz), 4.01 (t, 4H, J = 7.6 Hz), 4.20 (q, 2H, J = 7.2 Hz) and 5.73 (s, 1H); 13C NMR (CDCl3) delta 14.4, 16.1, 23.9, 49.9, 61.2, 95.0, 163.0, 167.7 and 170.1; mass spectrum (APCI), m/z 194.1289 (M+H)+ (C10H16N3O requires m/z 194.1293).

With the rapid development of chemical substances, we look forward to future research findings about 37482-64-7.

Reference:
Article; Chevalier, Arnaud; Alam, Mohammad Parvez; Khdour, Omar M.; Schmierer, Margaret; Arce, Pablo M.; Cripe, Cameron D.; Hecht, Sidney M.; Bioorganic and Medicinal Chemistry; vol. 24; 21; (2016); p. 5206 – 5220;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 16097-60-2, 2-Amino-4-chloro-6-(trifluoromethyl)pyrimidine, 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-Amino-4-chloro-6-(trifluoromethyl)pyrimidine, blongs to pyrimidines compound. Application In Synthesis of 2-Amino-4-chloro-6-(trifluoromethyl)pyrimidine

A mixture of 0.3 g (1.5 mmol) of 2-amino-4-chloro-6-trifluoromethylpyrimidine, 0.3 g (1.5 mmol) of (1R,2S)-2,6-dimethyl-2,3-dihydro-1H-inden-1-aminium chloride and 0.53 g (3.8 mmol) of potassium carbonate in 3 ml of dimethylformamide is heated at 120 C. for 5 hours. After cooling, the reaction mixture is adsorbed on silica gel and purified by means of column chromatography using ethyl acetate/heptane as eluent. Following concentration by evaporation, 0.24 g of solid N4[(1R,2S)-2,6-dimethyl-2,3-dihydro-1H-inden-1-yl]-6-(trifluoromethyl)pyrimidine-2,4-diamine is obtained (44% yield, 90% purity).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16097-60-2, 2-Amino-4-chloro-6-(trifluoromethyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER CROPSCIENCE AG; US2010/167935; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 34253-03-7, 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. 34253-03-7, name is Methyl pyrimidine-2-carboxylate. A new synthetic method of this compound is introduced below.

[0507] Synthesis of pyrimidin-2-ylmethanol: [0508] To a stirred solution of methyl pyrimidine-2-carboxylate (10.0 g, 72.46 mmol) in EtOH (100 mL) was added NaBH4 (3.85 g, 101.31 mmol) portion wise at 0 C under inert atmosphere. The reaction mixture was warmed to RT and stirred for 2 h. After completion of starting material by TLC, the volatiles were evaporated under reduced pressure. The residue was diluted with saturated K2C03 solution and extracted with EtOAc. The combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to afford pyrimidin-2-ylmethanol (4.5 g, crude) as yellow semi-solid. 1H-NMR (DMSO-d6, 400 MHz): delta 8.76 (d, 2H), 7.42 (t, 1H), 5.29 (br s, 1H), 4.61 (s, 2H); LC-MS: 94.12%; 111 (M++l) (column; Chromolith RP-18, (100×4.6 mm); RT 2.24 min. 5mM NH4OAc: ACN; 0.8 ml/min); TLC: 100% EtOAc (Rf: 0.2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,34253-03-7, its application will become more common.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew, J.; BURSAVICH, Matthew, Gregory; WO2013/142269; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 17180-94-8, 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. 17180-94-8, name is 5-Chloropyrimidine. A new synthetic method of this compound is introduced below.

Example 143 Compound 143: 5-(3,3-dimethyl-but-1-ynyl)-3-{(trans-4-methyl-cyclohexanecarbonyl)-[1-(S)-methyl-3-(pyrimidin-5-yloxy)-propyl]-amino}-thiophene-2-carboxylic acid The 5-(3,3-dimethyl-but-1-ynyl)-3-[(3-hydroxy-1-(S)-methyl-propyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid TFA salt (100 mg, 0.239 mmol) and 5-chloro-pyrimidine (137 mg, 1.194 mmol) were dissolved in DMSO (2 mL). To this solution tBuOK (107 mg, 0.956 mmol) was added in one portion at rt. The reaction was allowed to stir at rt for 1 h and then heated to 60 C. for 1.5 h. Additional tBuOK (50 mg) and 5-chloro-pyrimidine (69 mg) were added and the reaction was run at 60 C. for another 1 h. The reaction was then heated to 100 C. for another 1 h. Additional tBuOK (50 mg) and 5-chloro-pyrimidine (69 mg) were added and the reaction was run at 100 C. overnight. The reaction was cooled to rt and quenched with a 20% (v/v) solution of acetic acid in water. The reaction was diluted with MeOH and 5-(3,3-dimethyl-but-1-ynyl)-3-{(trans-4-methyl-cyclohexanecarbonyl)-[1-(S)-methyl-3-(pyrimidin-5-yloxy)-propyl]-amino}-thiophene-2-carboxylic acid (4 mg, 2.7%) was isolated by reverse phase HPLC as the TFA salt. LC/MS (m/z): 497.88 [M+1]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17180-94-8, its application will become more common.

Reference:
Patent; Gilead Sciences, Inc.; US2011/20278; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 943757-74-2, name is 2-(4-Methylpiperazin-1-yl)pyrimidin-5-amine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 943757-74-2

Preparation Example 4 A mixture of 3-chloro-6-ethyl-5-(3-nitrophenoxy)pyrazine-2-carboxamide (300 mg), 2-(4-methylpiperazin-1-yl)pyrimidine-5-amine (198 mg), and diisopropylethylamine (318 muL) in N-methylpyrrolidone (1.5 mL) was heated at 120 C. for 18 hours. The reaction mixture was cooled, and then diluted with ethyl acetate, and the organic phase was washed with water and saturated brine. After drying over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; chloroform:methanol:28% aqueous anunonia=1:0:0-95:4.5:0.5) to obtain 6-ethyl-3-{[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]amino}-5-(3-nitrophenoxy)pyrazine-2-carboxamide (234 mg) as a yellow solid.

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, 943757-74-2, 2-(4-Methylpiperazin-1-yl)pyrimidin-5-amine.

Reference:
Patent; ASTELLAS PHARMA INC.; Matsuya, Takahiro; Kondoh, Yutaka; Shimada, Itsuro; Kikuchi, Shigetoshi; Iida, Maiko; Onda, Kenichi; Fukudome, Hiroki; Takemoto, Yukihiro; Shindou, Nobuaki; Sakagami, Hideki; Hamaguchi, Hisao; US2014/323463; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 34253-03-7 ,Some common heterocyclic compound, 34253-03-7, molecular formula is C6H6N2O2, 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.

Step B: Preparation of pyrimidin-2-ylmethanol: A cold solution (0 C.) of methylpyrimidine-2-carboxylate (659 mg, 4.77 mmol) in EtOH (25 mL) was prepared, and sodium borohydride (181 mg, 4.77 mmol) was added. The reaction mixture was stirred at room temperature for 2 hours. The reaction was quenched with water (5 mL) and concentrated. The crude product was purified using silica gel chromatography to give the desired product as a white solid (154 mg, 30%). 1H NMR (400 MHz, CDCl3) delta8.76-8.75 (d, J=4.7 Hz, 2H), 7.27-7.25 (t, J=4.7 Hz, 1H), 4.87 (s, 2H), 4.10 (br s, 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. 34253-03-7, Methyl pyrimidine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Array Biopharma, Inc.; US2010/63066; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 14631-08-4 , The common heterocyclic compound, 14631-08-4, name is 2-Chloropyrimidine-4,5-diamine, molecular formula is C4H5ClN4, 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.

DIPEA (0.35 mL, 2.03 mmol) was added to a stirred suspension of 2-chloro-4,5- diaminopyrimidine (100 mg, 0.69 mmol), trans-(2S)-2-(tert-butoxycarbonylamino)-2-(4- methylcyclohexyl)acetic acid (271 mg, 0.99 mmol) and HATU (410 mg, 1.08 mmol) in DCM (5 mL) at 20C. The reaction mixture was stirred at 20C for 18 h, then diluted with DCM (15 mL) and washed with saturated aqueous NaHCO3 solution (10 mL). The organic layer was filtered through a hydrophobic frit, and the solvent was concentrated in vacuo. The resulting dark brown oil was dissolved in EtOH (10 mL), and K2CO3 (398 mg, 2.88 mmol) was added. The suspension was heated at 80C in a sealed vial for 40 h. After cooling, the mixture was diluted with water (10 mL), and the aqueous layer was extracted with DCM (3 x 15 mL). The combined organic extracts were filtered through a hydrophobic frit, and the solvent was concentrated in vacuo. The resultant dark brown oil was separated by flash column chromatography, eluting with EtOAc/heptane (0-50% gradient), to afford the title compound (80 mg, 30%) as a yellow oil that slowly solidified on standing. dH (250 MHz, CDCl3) 11.73 (br s, 1H), 8.90 (s, 1H), 5.87-5.64 (m, 1H), 4.74-4.62 (m, 1H), 1.75-1.68 (m, 4H), 1.41 (s, 9H), 1.28-1.04 (m, 6H), 0.88-0.84 (m, 3H). LCMS (Method 10): [M+H]+ m/z 380 and 382, RT 1.18 minutes.

The synthetic route of 14631-08-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB BIOPHARMA SPRL; BRACE, Gareth Neil; CHAPPELL, Rose Elizabeth; FOULKES, Gregory; FROST, James Richard; HORSLEY, Helen Tracey; JONES, Elizabeth Pearl; LECOMTE, Fabien Claude; REUBERSON, James Thomas; SCHULZE, Monika-Sarah Elisabeth Dorothea; TAYLOR, Richard David; YAU, Wei Tsung; ZHU, Zhaoning; (246 pag.)WO2019/138017; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1111237-76-3 ,Some common heterocyclic compound, 1111237-76-3, molecular formula is C7H5BrClN3, 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 solution of 5-bromo-4-chloro-2-methyl-7H-pyrrolo[2,3-Patent; LES LABORATOIRES SERVIER; VERNALIS (R&D) LIMITED; FIUMANA, Andrea; FOLOPPE, Nicolas; RAY, Stuart; WALMSLEY, David; KOTSCHY, Andras; BURBRIDGE, Michael, Frank; CRUZALEGUI, Francisco, Humberto; (141 pag.)WO2017/55533; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 52854-14-5, 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. 52854-14-5, name is 4-Chloro-6-methoxy-5-nitropyrimidine. A new synthetic method of this compound is introduced below.

General procedure: 4-chloro-6-methoxy-5-nitro-pyrimidine (Preparation R1a; 1.0 eq.), the appropriate phenol (1.2 eq.), and potassium carbonate (1.2 eq.) were dissolved in acetonitrile. It was stirred at 80 C till completion, then water was added to the reaction mixture. MeCN was evaporated. The residue extracted with DCM. The combined organic phase was dried over MgS04 and evaporated under reduced pressure to give R2a-R2ce.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,52854-14-5, 4-Chloro-6-methoxy-5-nitropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; LES LABORATOIRES SERVIER; VERNALIS (R&D) LIMITED; WEBER, Csaba; KOTSCHY, Andras; VASAS, Attila; KISS, Arpad; MOLNAR, Balazs; MACIAS, Alba; FIUMANA, Andrea; DAVIES, Nicholas; MURRAY, James Brooke; SELLIER, Emilie; DEMARLES, Didier; IVANSCHITZ, Lisa; GENESTE, Olivier; (233 pag.)WO2020/8013; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia