Month: September 2021

Reference of 46155-89-9, 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 46155-89-9, name is 1,3-Dimethyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 111 5-[4-(4-Chlorobenzoyl)benzyl]-1,3-dimethylpyrrolo [3,2-d]pyrimidine-2,4-dione To a solution of 1,3-dimethylpyrrolo[3,2-d]-pyrimidine-2,4-dione (0.402 g, 2.24 mmol) and 4-(4-chlorobenzoyl) benzyl bromide (1.20 g, 3.88 mmol) in DMF (5 ml) was added potassium carbonate (0.73 g, 5.28 mmol) and the mixture was stirred at 60 C. for 2 hours. The solvent was then distilled off under reduced pressure and the residue was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaCl solution, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developer: isopropyl ether: ethyl acetate: methylene chloride=2:1:1) and recrystallized from ethyl acetate to provide colorless needles. 0.360 g (39%) 1 H-NMR (CDCl3) delta: 3.40(3H,s), 3.49(3H,s), 5.66(2H,s), 6.00(1H,d,J=3.0 Hz), 7.01(1H,d,J=3.0 Hz), 7.29(2H,d,J=8.6 Hz), 7.45(2H,d,J=8.6 Hz), 7.72(2H,d,J=8.6 Hz),,7.73(2H,d,J=8.6 Hz). IR (KBr): 1693, 1653, 1549, 1466, 1434, 1406, 1267, 1065, 1016, 962, 922, 856, 744, 669, 503 cm-1.

According to the analysis of related databases, 46155-89-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US5753664; (1998); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 89793-12-4, 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. 89793-12-4, name is Ethyl 2-chloropyrimidine-5-carboxylate. A new synthetic method of this compound is introduced below.

Step 1: A mixture of ethyl 2-chloropyrimidine-5-carboxylate (1.86 g, 10 mmol), compound 1 (4-amino-l-Boc-piperidine, 3.00 g, 15 mmol), and NEt3 (3.0 g, 30 mmol) in 1,4-dioxane (20 mL) was stirred at 95°C overnight. The mixture was concentrated, and EA (60mL) and aqueous citric acid (60 mL) were added to the mixture followed by stirring the mixture for 30 min. The organic layer was collected, dried and concentrated to get compound 2 (3.4 g, yield: 97percent) as a light yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89793-12-4, Ethyl 2-chloropyrimidine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ACETYLON PHARMACEUTICALS, INC.; SHEARSTONE, Jeffrey, R.; JARPE, Matthew, B.; (152 pag.)WO2016/57779; (2016); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 22536-63-6, 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. 22536-63-6, name is 2-Chloro-4-methoxypyrimidine, molecular formula is C5H5ClN2O, 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.

To a solution of cis-1-(3-methoxyphenyl)-4-piperazin-1-ylcyclohexanecarbonitrile dihydrochloride (50 mg, 0.134 mmol), triethylamine (0.0654 ml, 0.469 mmol) and potassium carbonate (92.6 mg, 0.670 mmol) in N,N-dimethylformamide (DMF, 1.5 mL), 2-chloro-4-methoxypyrimidine (29.1 mg, 0.201 mmol) was added at room temperature, and then the mixture was heated to 70C and stirred for 5 hours. Water was added thereto to quench the reaction, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water twice, dried over anhydrous magnesium sulfate, filtrated, and the solvent was removed from the filtrate in vacuo. The residue was purified by silica gel chromatography to give 39.3 mg of the title compound as a white crystal. High-performance liquid chromatography/mass spectrometry m/z 408.4 (M+H) Retention time: 2.36 min.

According to the analysis of related databases, 22536-63-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; EP1679069; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 16097-63-5, 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 16097-63-5, name is 4-Chloro-2-(methylsulfanyl)-6-(trifluoromethyl)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

A 250-mL round bottom flask was charged with 4-chloro-2-(methylthio)-6- (trifluoromethyl)pyrimidine (2.50 g, 10.9 mmol) in dichloromethane (20 mL). To this solution at 0 C was added a solution of m-CPBA in dichloromethane (40 mL) over 7 minutes. After stirring for 7 h, the reaction mixture diluted with dichloromethane and washed with saturated sodium thiosulfate (25 mL), saturated sodium carbonate (2 x 10 mL), and saturated sodium chloride (2 x 10 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford the title compound (2.89 g, 100%) as a white solid. MW = 260.62. ]H NMR (CDC13, 300 MHz) delta 7.90 (s, 1H), 3.44 (s, 3H).

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 16097-63-5, 4-Chloro-2-(methylsulfanyl)-6-(trifluoromethyl)pyrimidine.

Reference:
Patent; TETRA DISCOVERY PARTNERS, LLC.; GURNEY, Mark, E.; HAGEN, Timothy, J.; MO, Xuesheng; VELLEKOOP, A.; ROMERO, Donna, L.; CAMPBELL, Robert, F.; WALKER, Joel, R.; ZHU, Lei; WO2014/66659; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 428854-24-4, 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. 428854-24-4, name is 2-(1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidine-4,5,6-triamine, molecular formula is C17H15FN8, 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.

Example 17A 2-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-N-5-(2,2,2-trifluoroethyl)pyrimidine-4,5,6-triamine 500 mg (1.427 mmol) of the compound from example 1A were admixed with 3.5 ml of dimethylformamide and 1205 mg (4.281 mmol) of 2,2,2-trifluoroethyl trichloromethanesulfonate, and the mixture was heated at 150 C. in a microwave for 1 h. The reaction mixture was concentrated under reduced pressure, and the residue was purified by means of preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 50:50?70:30). 236 mg of the title compound were obtained (29% of theory). LC-MS (method 2): Rt=0.87 min; MS (EIpos): m/z=433 (M+H)+. 1H NMR (400 MHz, DMSO-d6): delta [ppm]=3.43-3.53 (m, 2H), 4.05 (t, 1H), 5.78 (s, 2H), 6.13 (s br, 4H) 7.10-7.15 (m, 2H), 7.20-7.25 (m, 1H), 7.32-7.38 (m, 2H), 8.60 (dd, 1H), 9.04 (dd, 1H).

According to the analysis of related databases, 428854-24-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Follmann, Markus; Stasch, Johannes-Peter; Redlich, Gorden; Ackerstaff, Jens; Griebenow, Nils; Knorr, Andreas; Wunder, Frank; Li, Volkhart Min-Jian; Baerfacker, Lars; Weigand, Stefan; US2014/148433; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 149849-92-3, 2-Chloropyrimidine-4-carboxylic acid, 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, Quality Control of 2-Chloropyrimidine-4-carboxylic acid, blongs to pyrimidines compound. Quality Control of 2-Chloropyrimidine-4-carboxylic acid

In a 100 mL flask was 2-chloropyrimidine-4-carboxylic acid (216 mg, 1.362 mmol) and 6-fluoro-4-(2-vinylmorpholino)pyridin-3-amine (304 mg, 1.362 mmol) in Ethyl acetate (3 mL) to give a tan solution. Hunig’s base (0.713 mL, 4.09 mmol) and 1- propanephosphonic acid cyclic anhydride (2.432 mL, 4.09 mmol) were added. The mixture was stirred at rt over the weekend for 66 h. LCMS showed conversion to the desired product. The mixture was basified with IN NaOH and diluted with EtOAc and water. The layers were separated. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with water, brine, dried and concentrated to afford the desired product (459 mg, 93%) as a tan oil/solid: 1H NMR (400 MHz, Chloroform-d) delta 10.51 (s, 1H), 9.24 (d, J = 0.7 Hz, 1H), 8.93 (d, J = 4.9 Hz, 1H), 8.13 (d, J = 4.9 Hz, 1H), 6.64 (d, J = 1.9 Hz, 1H), 5.51 (ddd, J = 17.8, 10.3, 7.7 Hz, 1H), 5.19 – 5.09 (m, 2H), 4.09 – 3.96 (m, 3H), 3.75 (td, J = 7.8, 2.9 Hz, 1H), 3.67 (dd, J = 11.2, 8.0 Hz, 1H), 3.11 (dt, J = 12.1, 3.1 Hz, 1H), 2.82 (ddd, J = 12.2, 9.1, 3.1 Hz, 1H); 19F NMR (376 MHz, Chloroform-d) delta -69.23; MS (ESI) (m/z): 364.2 (M+H)+.

The synthetic route of 149849-92-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LUO, Guanglin; SIVAPRAKASAM, Prasanna; DUBOWCHIK, Gene M.; MACOR, John E.; (45 pag.)WO2018/98413; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 45695-56-5, 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. 45695-56-5, name is Pyrimidine-2-carboximidamide. A new synthetic method of this compound is introduced below.

Compound 159 Enantiomers of racemic mixture 159: 159a and 159b A mixture of compound 129 (4 g crude), 2-pyrimidinecarboximidamide (2.35 g, 19.2 mmol) and 1 , 4-dioxane (25 mL) was stirred at 40C for 72 hours and allowed to reach room temperature. The reaction mixture was evaporated to dryness to afford a brown residue. This residue and phosphorus oxychloride (20.9 mL, 225 mmol) were stirred at 120C for 45 minutes in a round bottomed flask. The reaction mixture was concentrated in vacuo at 50C and co evaporated with toluene (2 x 100 mL). The residue was dissolved in dichloromethane (250 mL) and washed with saturated aqueous sodium bicarbonate (100 mL), dried (Na2S04) and evaporated to afford a dark brown residue. This residue was purified using silica gel column chromatography (dichloromethane in heptane from 50 to 100%) to methyl 6-chloro-4-(3,4- difluorophenyl)-4-methyl-2-(pyrimidin-2-yl)- 1 ,4-dihy dropyrimidine-5 -carboxylate (1800 mg) as light yellow solid. A solution of methyl 6-chloro-4-(3,4-difluorophenyl)- 4-methyl-2-(pyrimidin-2-yl)-l,4-dihy dropyrimidine-5 -carboxylate (900 mg) in 1 , 4- dioxane (10 mL) in a microwave-vial was stirred and purged with nitrogen for 10 minutes. Then tetramethyltin (494 mu, 3.56 mmol) was added followed by bis (tri-t- butylphosphine) palladium (0) (243 mg, 0.475 mmol) and the vial was flushed with nitrogen and capped. The reaction mixture was heated under microwave irradiation at 140C for 30 minutes and allowed to reach room temperature. The reaction mixture was stirred and purged with nitrogen for 10 minutes, bis(tri-t-butylphosphine) palladium (0) (121 mg, 0.238 mmol) was added and the vial was flushed with nitrogen and capped. The reaction mixture was heated by microwave irradiation at 145C for 30 minutes and allowed to reach room temperature. The reaction mixture was concentrated in vacuo. The obtained residue was mixed with dichloromethane (100 mL) and the orange precipitate was filtered off. The filtrate was washed with water (2 x 20 mL), dried (Na2S04) and concentrated in vacuo. The obtained residue was purified using silica gel column chromatography (ethyl acetate in heptane from 20 to 100%) to afford compound 159 as yellow sticky oil. Method A; Rt: 0.86 m/z; 359.2 (M+H)+ Exact mass: 358.1.Racemix mixture 159 was purified by Prep SFC (Stationary phase: Chiralpak Diacel AD 30 x 250 mm), Mobile phase: C02, Ethanol), yielding compound 159a and 159b as yellow powders. Columns: AD-H 250 mm x 4.6 mm; Flow: 3 ml/min; Mobile phase: 10 % EtOH (containing 0.2% iPrNH2) hold 15.00 min; Temperature: 30C; compound 159a: Rt (3.2 min), compound 159b Rt (4.5 min). 1H NMR (360 MHz, CHLOROFORM- , tautomeric mixture (-9/1), main isomer desribed) delta ppm 1.96 (s, 3 H), 2.34 (s, 3 H), 3.49 (s, 3 H), 7.04 (dt, J=10.0, 8.0 Hz, 1 H), 7.19 – 7.24 (m, 1 H), 7.30 (ddd, J=12.0, 8.0, 3.0 Hz, 1 H), 7.40 (t, J=5.0 Hz, 1 H), 8.41 (br. s., 1 H), 8.86 (d, J=5.0 Hz, 2 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,45695-56-5, its application will become more common.

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin Yvonne Paul; ROMBOUTS, Geert; VERSCHUEREN, Wim Gaston; RABOISSON, Pierre Jean-Marie Bernard; WO2013/102655; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1260088-72-9, 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.1260088-72-9, name is 2,4-Dichloro-7,7-dimethyl-5,7-dihydrofuro[3,4-d]pyrimidine, molecular formula is C8H8Cl2N2O, molecular weight is 219.0679, as common compound, the synthetic route is as follows.

General procedure: A mixture of 2,4-dichloro-7,7-dimethyl-5,7-dihydrofuro[3,4-d]pyrimidine7 (257mg, 1.173 mmol), 1H-pyrazolo[4,3-c]pyridin-3-amine (291 mg, 1.735 mmol), N,N-diisopropylethylamine (0.40 mL, 2.3 mmol) and N,N-dimethylformamide (4.0 mL) was heated at 70 C for 2 hours. The reaction mixture was diluted with ethyl acetate, washed with water (2x) and brine, dried over magnesium sulfate, filtered, and evaporated in vacuo. The crude product was purified via flash chromatography on silica gel (24 silica, solvent gradient: 0-100% ethyl acetate in dichloromethane followed by 10% methanol indichloromethane) to yield 176.7 mg of the title compound.

Statistics shows that 1260088-72-9 is playing an increasingly important role. we look forward to future research findings about 2,4-Dichloro-7,7-dimethyl-5,7-dihydrofuro[3,4-d]pyrimidine.

Reference:
Article; Hanan, Emily J.; Baumgardner, Matt; Bryan, Marian C.; Chen, Yuan; Eigenbrot, Charles; Fan, Peter; Gu, Xiao-Hui; La, Hank; Malek, Shiva; Purkey, Hans E.; Schaefer, Gabriele; Schmidt, Stephen; Sideris, Steve; Yen, Ivana; Yu, Christine; Heffron, Timothy P.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 2; (2016); p. 534 – 539;,
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. 149849-94-5, name is Methyl 2-chloropyrimidine-4-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of Methyl 2-chloropyrimidine-4-carboxylate

A solution of 5-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-4-(trifluoromethyl)-2-[[2-(trimethylsilyl)ethoxy]methyl]-2,3-dihydropyridazin-3-one (500 mg, 1.27 mmol, 1.00 equiv), (Pd(allyl)C)2 (47 mg, 0.10 equiv), Rockphos (60 mg, 0.10 equiv), Cs2CO3 (829 mg, 2.54 mmol, 2.00 equiv), methyl 2-chloropyrimidine-4-carboxylate (547 mg, 3.17 mmol, 2.50 equiv) in toluene (10 mL) under nitrogen atmosphere was stirred overnight at 85 C. The solvent was concentrated under vacuum and the residue was applied onto a silica gel column eluting with EtOAc/petroleum ether (3/7) to afford 425 mg (63%) of the title compound as a yellow solid. LCMS (ESI, m/z): 530.20 [M+H]+.

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, 149849-94-5, Methyl 2-chloropyrimidine-4-carboxylate.

Reference:
Patent; Ribon Therapeutics Inc.; Vasbinder, Melissa Marie; Schenkel, Laurie B.; Swinger, Kerren Kalai; Kuntz, Kevin Wayne; (410 pag.)US2019/330194; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 13418-77-4, 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.13418-77-4, name is 2-Amino-5-methoxypyrimidine, molecular formula is C5H7N3O, molecular weight is 125.13, as common compound, the synthetic route is as follows.

General procedure: A 0.5 – 2.0 mL microwave vessel was charged with carboxylic acid VII (251 mg, 0.534 mmol) and this was dissolved in NMP (2 mL). HATU (223 mg, 0.587 mmol) andDIPEA (0.102 mL, 0.587 mmol) were then added and the resultant mixture was stirred at room temperature for 30 min. 2-amino-5-trifluoromethylpyridine (130 mg, 0.801 mmol) was then added and the vessel was tightly sealed with a crimp top. The resultant mixture was heated thermally in a heating block to 110 C for 16 h. The mixture was then diluted with EtOAc and washed with successively with sat. NH4Cl (aq) (1X), sat. NaHCO3 (aq) (1X), H2O (1X) and brine (1X). The organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was then purified by FCC (12 g SiO2, gradient elution with 0-5% MeOH/DCM). The semi-pure material obtained was then further purified by FCC (12 g SiO2, gradient elution with 0-100% EtOAc/hexanes) and then purified further by FCC (12 g SiO2, gradient elution with 0-5% MeOH/EtOAc) to provide 170 mg (52%) of 11d.

Statistics shows that 13418-77-4 is playing an increasingly important role. we look forward to future research findings about 2-Amino-5-methoxypyrimidine.

Reference:
Article; Letourneau, Jeffrey J.; Stroke, Ilana L.; Hilbert, David W.; Cole, Andrew G.; Sturzenbecker, Laurie J.; Marinelli, Brett A.; Quintero, Jorge G.; Sabalski, Joan; Li, Yanfang; Ma, Linh; Pechik, Igor; Stein, Philip D.; Webb, Maria L.; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3601 – 3605;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia