Category: pyrimidines

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.55405-67-9, name is 3-Bromopyrazolo[1,5-a]pyrimidine, molecular formula is C6H4BrN3, molecular weight is 198.0201, as common compound, the synthetic route is as follows.COA of Formula: C6H4BrN3

To a stirred solution of compound 13f (27.8 mmol) in 1,4-dioxane (120 mL) was added B2Pm2 (126 mmol) and KOAc (101 mmol) at rt. The resulting mixture was purged with Ar for 45min, PdCl2(PPli3)2 (1.5 mmol) was added and the mixture again purged with Ar for 30min. The resulting mixture was heated to 1000C for 15h. The reaction mixture was concentrated to obtain a viscous mass, which was charged over afluorosil plug, washed with pentane, followed by 60% EtOAc/Pet ether. The relevant fractions were concentrated to obtain a crude compound 13g as a pale yellow solid. The crude compound 13g was stirred with pentane (25mL) at -400C for 30min, filtered, washed with cold pentane (5mL) and dried under vacuum to obtain sufficiently pure compound (3.5g, 51.4%). TLC system: Ethyl acetate: Petroleum ether (2:3) Rf value: 0.4. (M + H): 246.3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,55405-67-9, 3-Bromopyrazolo[1,5-a]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2009/85913; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
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.60703-46-0, name is 2,4,6-Trichloro-5-methoxypyrimidine, molecular formula is C5H3Cl3N2O, molecular weight is 213.4491, as common compound, the synthetic route is as follows.Computed Properties of C5H3Cl3N2O

Step 3: Under an atmosphere of nitrogen a solution of 2,4,6-trichloro-5-methoxy- pyrimidine (4.0 g, 18.7 mmol) in DCM (200 mL) was cooled to 0C and treated with boron tribromide (neat, 6.6 mL, 65 mmol) dropwise. After stirring for 18 hours at room temperature LCMS analysis indicated complete reaction. The reaction mixture was cooled and carefully diluted with methanol (25 mL) and the reaction mixture diluted with water (200 mL). The aqueous layer was washed with DCM and the combined organic extracts dried (Na2S04) filtered and concentrated in vacuo to give 2,4,6-trichloro-5-hydroxy-pyrimidine as a pale tan solid (2.55 g, 71%). 13C NMR (DMSO-de): 149.23 (C), 145.25 (C), 145.08 (C). LCMS: RT= 2.65/2.77 [M- H]-= 197/199.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,60703-46-0, 2,4,6-Trichloro-5-methoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA-ROCHE AG; DOTSON, Jennafer; HEALD, Robert Andrew; HEFFRON, Timothy; JONES, Graham Elgin; KRINTEL, Sussie Lerche; MCLEAN, Neville James; NDUBAKU, Chudi; OLIVERO, Alan G.; SALPHATI, Laurent; WANG, Lan; WEI, BinQing; WO2012/82997; (2012); A1;,
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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 101257-82-3, name is 4-Amino-5-chloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 4-Amino-5-chloropyrimidine

AA. [4-(2-Chloro-ethoxy)-3-methyl-pyridin-2-ylmethyl]-(5-chloro-pyrimidin-4-yl)-amine The compound is obtained analogously to Example K starting with ethylenglycol and 4-chloro-2,3-dimethyl-pyridine-N-oxide and reaction of 4-amino-5-chloro-pyrimidine with 4-(2-chloro-ethoxy)-2-chloromethyl-3-methyl-pyridine in the last step.

With the rapid development of chemical substances, we look forward to future research findings about 101257-82-3.

Reference:
Patent; BYK Gulden Lomberg Chemische Fabrik GmbH; US6395732; (2002); B1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 163263-91-0, 2,4-Dichloro-6-(4-methoxyphenyl)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, HPLC of Formula: C11H8Cl2N2O, blongs to pyrimidines compound. HPLC of Formula: C11H8Cl2N2O

1H-NMR (300 MHz, CDCl3): delta (ppm) 8.91 (d, J= 3.0 Hz, 1H), 8.76 (m, 4H), 8.39 (d, J = 9.0 Hz, 2H), 7.92 (m, 2H), 7.58-7.38 (t, J = 8.0 Hz, 2H), and 7.06(d, J = 9.0 Hz, 2H), 3.91 (s, 3H); 13C-NMR (75 MHz, DMSO-d6): delta (ppm) 165.2, 163.9, 163.6, 162.1, 155.6,154.4, 150.1, 149.4, 137.1, 136.8, 129.5, 129.2, 125.6, 124.6, 124.1, 122.4, 114.2, 111.1, and 55.4; and LRMS(ESI-MS) m/z = 341.13 [M + H]+In a dry round-bottomed flask, 2,4-dichloro-6-(4-methoxyphenyl)pyrimidine (677 mg, 2.65mmol, 1.0 eq) and Pd(Ph3)4 (460 mg, 0,39 mmol, 0.15 eq) are introduced under argon atmosphere. Dry toluene (20 mL) is added, and a cooling system is installed. The mixture is degassed for 10 min before the addition of 2-(tributylstannyl)pyridine (2.1 mL, 6.63 mmol, 2.5 eq) and heated at reflux (110 C)for 15 h. Then, 30 mL of water is added. The crude mixture is filtrated on a pad of celite and washed with ethyl acetate, followed by extraction. The combined organic phase is dried over MgSO4, filtered and concentrated to dryness. The product is purified by column chromatography (Al2O3-cyclohexane/AcOEt 50/50) to afford the expected product (749 mg, 83%).

The synthetic route of 163263-91-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Morel, Elodie; Beauvineau, Claire; Naud-Martin, Delphine; Landras-Guetta, Corinne; Verga, Daniela; Ghosh, Deepanjan; Achelle, Sylvain; Mahuteau-Betzer, Florence; Bombard, Sophie; Teulade-Fichou, Marie-Paule; Molecules; vol. 24; 3; (2019);,
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Pyrimidine – Wikipedia

Synthetic Route of 14631-08-4, 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 14631-08-4, name is 2-Chloropyrimidine-4,5-diamine. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 1; { 5 – [4-(2-Bromo-5 -fluorophenoxy)piperidin- 1 -yl] -3H- [ 1 ,2,3 ] triazolo [4,5 -d] pyrimidin-3 -yl } acetic acid; Step 1 : 2-[4-(2-Bromo-5-fluorophenoxy)piperidin-l-yllpyrimidine-4,5-diamine; A mixture of 2-chloropyrimidine-4,5-diamine (3 g, 20.75 mmol), 4-(2- bromophenoxy)piperidine (6.83 g, 24.90 mmol) and etaunig’s base (7.25 ml, 41.5 mmol) in 2- methoxyethanol (33.2 mL) and water (8.30 mL) was heated at 130 0C for 6 d. The solvent was evaporated, the residue diluted with water (25 mL) and extracted three times with EtOAc (25 mL). The combined organic fractions were dried over Na2SO4 and the solvent evaporated. Purification by Combiflash (SiO2-120 g, gradient elution of 5% MeOeta/EtOAc over 25 min) afforded the title product as a solid. leta NMR (500 MHz, acetone-d6): delta 7.57 (dd, 1 H), 7.53 (s, 1 H), 7.04 (dd, 1 H), 6.70 (td, 1 H),5.55 (s, 2 H), 4.78-4.73 (m, 1 H), 4.05-3.97 (m, 2 H), 3.58-3.51 (m, 2 H), 3.42 (s, 2 H), 2.00- 1.92 (m, 2 H), 1.74-1.66 (m, 2 H). MS (+ESI) m/z 382, 384 (MH+).

According to the analysis of related databases, 14631-08-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK FROSST CANADA LTD.; WO2009/12573; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 57401-76-0, 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. 57401-76-0, name is Ethyl 2-aminopyrimidine-5-carboxylate. A new synthetic method of this compound is introduced below.

To a solution of ethyl 2-aminopyrimidine-5-carboxylate (0.200 g, 1.196 mmol) in DME (6 ml), a suspension of sodium 2-methylbutan-2-olate (0.527 g, 4.79 mmol) in DME (6 ml) was added drop wise stirring at room temperature under nitrogen. The resulting yellow suspension was stirred at the same temperature for 30 minutes and then cooled to -10 C. Methanesulfonyl chloride (0.278 ml, 3.59 mmol) was added drop wise maintaining the temperature below -5 C. After 1.5 hours, water (30 ml) was added, and the mixture was extracted with ethyl acetate (20 ml×3). The combined organic layers were dried over sodium sulfate and evaporated. The residue was triturated with MeOH and the mother liquors were evaporated and triturated with EtOH. The two portions collected by filtration were mixed affording 0.152 g of a mixture of ethyl 2-(methylsulfonamido)pyrimidine-5-carboxylate and methyl 2-(methylsulfonamido)-pyrimidine-5-carboxylate (about 1:1 ratio). This mixture was suspended in THF (6.380 ml) and 3N NaOH (0.425 ml, 1.276 mmol) was added. The resulting solution was heated to 50 C. for 2.5 hours. THF was evaporated and the aqueous solution was diluted with water (2 ml) and acidified with 6N HCl (pH=2) stirring at room temperature. The obtained precipitate was collected by filtration affording 2-(methylsulfonamido)-pyrimidine-5-carboxylic acid as a white solid (0.133 g, 0.612 mmol, 51.1% yield, MS/ESI+ 218.0 [MH]+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,57401-76-0, Ethyl 2-aminopyrimidine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Chiesi Farmaceutici S.p.A.; ARMANI, Elisabetta; Amari, Gabriele; Capaldi, Carmelida; Esposito, Oriana; Peretto, Ilaria; US2013/79313; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
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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. 34415-10-6, name is 2-Methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid. A new synthetic method of this compound is introduced below., SDS of cas: 34415-10-6

6-Hydroxy-2-methylpyrimidine-4-carboxylic acid (5 g, 32.4 mmol) was added to phosphoryl trichloride (30 mL) at RT and the mixture was stirred at 105 C for 2 h. After cooling to RT, the solution wasconcentrated under reduced pressure. MeOH (30 mL) was added to the mixture dropwise at 0 C andthe solution was stirred for 16 h at RT. The solution was concentrated under reduced pressure. The resulting mixture was quenched by the addition of saturated aqueous sodium bicarbonate (50 mL) and the product was extracted with ethyl acetate (2 x 100 mL). The combined organic extracts were dried with anhydrous sodium sulfate and filtered. The title compound was obtained as a solid andwas used in the next step directly without further purification. MS = 183.1 (+ESI).

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, 34415-10-6, 2-Methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid.

Reference:
Patent; MERCK SHARP & DOHME CORP.; SHEN, Dong-Ming; WILSON, Jonathan, E.; MCCRACKEN, Troy; (95 pag.)WO2016/179059; (2016); A1;,
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Electric Literature of 313339-35-4, 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.313339-35-4, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid, molecular formula is C6H4Cl2N2O2S, molecular weight is 239.08, as common compound, the synthetic route is as follows.

A 50-mL 3 -necked round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, was charged with a solution of 4,6-dichloro-2-(methylthio)pyrimidine-5-carboxylic acid (700 mg, 2.93 mmol, 1.50 equiv) and N,N-dimethylformamide (1 drop) in dichloromethane (10 mL). The solution was treated with oxalyl chloride (750 mg, 5.91 mmol, 3.00 equiv) dropwise with stirring, stirred for 2 h at room temperature and then treated with a solution of Intermediate 2 (800 mg, 1.97 mmol, 1.00 equiv) in dichloromethane (10 mL) and DIE A (2 mL) dropwise with stirring at 0 C. The resulting solution was stirred for an additional 1 h at room temperature, concentrated under vacuum and the residue was purified by chromatography on silica gel (1 : 10 ethyl acetate/petroleum ether) to afford the title compound as a colorless oil. HPLC/MS: 626 (M+H+); Rt 4.78 min (LC4).

The chemical industry reduces the impact on the environment during synthesis 313339-35-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; INTERVET INTERNATIONAL B.V.; GRAHAM, Thomas; SHEN, Dong-Ming; LIU, Wensheng; WU, Zhicai; NARGUND, Ravi, P.; DE VITA, Robert, J.; BALKOVEC, James, M.; YU, Yang; WO2013/68439; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1618-36-6, 4-Chloro-5-methyl-7H-pyrrolo[2,3-d]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, Formula: C7H6ClN3, blongs to pyrimidines compound. Formula: C7H6ClN3

A. Preparation of 4,5-dichloro-7H-pyrrolo[2,3-d]pyrimidine; Following the procedure in Pdulo, J. S.; Saxena, N. K.; Nassiri, M. R.; Turk, S. R.; Drach, J. C.; Townsend, L. B. J. Med. Chem. 31:2086 (1988), 4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (Example 1A, 20. g, 0.13 mol) was suspended in anhydrous dichloromethane (500 mL), followed by addition of N-chlorosuccinimide (20.8 g, 0.160 mol). The reaction mixture was refluxed at 43 C. for 8 hours. The reaction was cooled down, and the white solid was filtered, washed with dichloromethane (300 mL), and dried to give 4,5-dichloro-7H-pyrrolo[2,3-d]pyrimidine (20 g, 83%)

The synthetic route of 1618-36-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rawlins, David Brent; Voronkov, Michael Victor; Zhang, Yulian; US2006/189638; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 259809-79-5, 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.259809-79-5, name is tert-Butyl 7,8-dihydro-2-(methylsulfonyl)pyrido[4,3-d]pyrimidine-6(5H)-carboxylate, molecular formula is C13H19N3O4S, molecular weight is 313.3727, as common compound, the synthetic route is as follows.

Stage 4: tert-Butyl 2-(dimethylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylateA mixture of tert-butyl 2-(methylsulfonyl)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (2.8 g, 8.95 mmol, 1.0 eq.), dimethylamine HCl (1.09 g, 13.42 mmol, 1.5 eq.) and DIPEA (4.37 ml, 25.56 mmol, 4.0 eq.) in NMP (6.5 ml) was stirred for 1 hour at 130° C. in a microwave.The reaction mixture was diluted with water (100 ml) and extracted with ethyl acetate (2*150 ml).The combined org.phases were washed with sat. NaCl solution (200 ml), dried over sodium sulfate, concentrated under reduced pressure and purified by column chromatography (silica gel, 18percent ethyl acetate in hexane). Yield: 78percent (1.95 g, 7.01 mmol)

The chemical industry reduces the impact on the environment during synthesis 259809-79-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GRUENENTHAL GmbH; US2012/71461; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia