Month: March 2022

Application of 42839-08-7, Adding some certain compound to certain chemical reactions, such as: 42839-08-7, name is Ethyl pyrimidine-2-carboxylate,molecular formula is C7H8N2O2, 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 42839-08-7.

General procedure: To the solution of ester (10 mmol) in THF (20 mL) and ethyl acetate (70 mmol), LiHMDS (30 mmol) was added very quickly at -40 C, and stirred at this temperature for 20 min. After completion of the reaction, reaction mixture was quenched with acetic acid (50 mmol) and then basified using 10% NaHCO3 solution, extracted with ethyl acetate (2×100 mL), the combined organic layer was washed with water and brine solution and dried over Na2SO4. The specific purification procedure for each compound has been included along with their characterization data.

According to the analysis of related databases, 42839-08-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Venkat Ragavan; Vijayakumar; Rajesh; Palakshi Reddy; Karthikeyan; Suchetha Kumari; Bioorganic and Medicinal Chemistry Letters; vol. 22; 12; (2012); p. 4193 – 4197;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 313339-35-4, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid, the common compound, a new synthetic route is introduced below. Recommanded Product: 313339-35-4

To a mixture of 4,6-dichloro-2-(methylsulfanyl)pyrimidine-5-carboxylic acid (1.50 g) and dichloromethane (15 mL), oxalyl chloride (1.20 mL) and DMF (0.015 mL) were added under ice cooling and stirred 30 minutes under ice cooling and 2 hours at room temperature. The solvent was distilled off under reduced pressure, followed by an azeotropic process with toluene. The resulting residue was dissolved in THF, followed by dropwise addition of 40% aqueous methylamine at -10 C. After the dropwise addition was completed, the reaction liquid was concentrated, and water was added. The resulting solid was collected by filtration and washed with water to give a white solid. The solid was dissolved in ethyl acetate, washed with saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. The solvent was distilled off. To a mixture of the resulting residue and dioxane (20 mL), 3-(methylsulfonyl)aniline hydrochloride (432 mg) and N,N-diisopropylethylamine (0.73 mL) were added and stirred at 100 C. for 4 hours. After cooling, the reaction liquid was diluted with ethyl acetate and washed with saturated aqueous sodium chloride. After drying over anhydrous magnesium sulfate, the solvent was distilled off, and the residue was purified by silica gel column chromatography (eluent; chloroform_methanol=100:0 to 30:1) to give 4-chloro-N-methyl-2-(methylsulfanyl)-6-{[3-(methylsulfonyl)phenyl]amino}pyrimidine-5-carboxamide (445 mg) as a white solid

The synthetic route of 313339-35-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Waters Technologies Corporation; US2012/40968; (2012); 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.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

Reference of 1801-06-5 ,Some common heterocyclic compound, 1801-06-5, molecular formula is C5H4ClFN2O, 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 100 ml dichloroethane and 25 ml acetonitrile as a solvent. Using dichloroethane as a solvent, the first 100 ml dichloroethane and 25 ml acetonitrile is poured into the 250 ml flask is, by adding 14.4g (0.1mol) of 2-methoxy-5-fluoro-4-hydroxy-pyrimidine. After dropwise 32.2g (0.3mol) of phosphorus oxychloride, within half an hour after the dropping, the stirring 10 minutes later, start dropwise triethylamine 21.2g (0.21mol), heating to 60 °C, stirring 2 hours later, cooling. In the reaction solution is poured into the crushed ice, to be layered. Applying the organic phase is 2-methoxy-4-chloro-5-fluoro pyrimidine dichloroethane solution.Then, 15 g of hydrazine hydrate were added dropwise thereto, and the mixture was heated to 70 ° C and reacted 2h, and the reaction was monitored by HPLC. The product was obtained as white needle crystals. 2-Methoxy-4-hydrazino-5-fluoro pyrimidine 11.98g (0.075 mol), m.p. 187 ° -188 ° C, product content 98.5percent, yield 77percent.

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. 1801-06-5, 4-Chloro-5-fluoro-2-methoxypyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shenyang Sinochem Pesticide Chemical R & D Co., Ltd; Cao, Wei; Sun, Ke; Guan, Yunfei; Pei, Heying; Li, Yanjuan; (6 pag.)CN105801492; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 69696-37-3 , The common heterocyclic compound, 69696-37-3, name is 5-Bromo-2,4-dimethylpyrimidine, molecular formula is C6H7BrN2, 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 tetrahydropyran-4- amine (1.35 g, 13.4 mmol) in toluene (5 ml) was added 5-bromo-2,4- dimethyl-pyrimidine (500 mg, 2.67 mmol), BINAP (333 mg, 0.53 mmol), Cs2C03 (1.74 g, 5.35 mmol) and Pd(OAc)2 (60 mg, 0.27 mmol) at rt under N2. The mixture was heated at 120 C for 3 h under a N2 atmosphere. H20 (10 ml) was added and the mixture was extracted with EtOAc (3 x 10 ml). The combined organic layers were washed with brine (5 ml), dried over Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was purified by FCC (0 – 50 % MeOH in EtOAc) to give the title compound as a brown solid (Y = (1619) 90 %). H NMR (400 MHz, methanol-^) d ppm 7.98 (s, 1H), 4.02 – 3.99 (m, 2H), 3.62 – 3.54 (m, 3H), 2.51 (s, 3H), 2.39 (s, 3H), 2.05 – 1.92 (m, 2H), 1.66 – 1.56 (m, 2H).

The synthetic route of 69696-37-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NODTHERA LIMITED; HARRISON, David; WATT, Alan Paul; BOCK, Mark G.; (334 pag.)WO2019/121691; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 69205-79-4, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 69205-79-4 as follows.

Anew synthesis of 7-formyl-preQ0 (systematic name, 2-amino-5-formylpyrrolo[2,3-d]pyrimidin-4-one) that, contrary to literature-known procedures (21-23), does not require protecting group chemistry was developed. PreQ0 (808 mg, 4.61 mmol)and sodium hypophosphite dihydrate (1.44 g, 13.6 mmol) were dissolved in the solvent mixture (15 ml of pyridine/acetic acid/deionized water in a ratio of 2:1:1) and stirred under inert atmosphere.Raney nickel catalyst (slurry in water, 500 mg) wasadded to the stirred reaction mixture. Safety precaution: dryRaney nickel is pyrophoric and should always be handled underinert atmosphere. The resulting reaction mixture was heated to50 C for 5 h. Subsequently, the reaction mixture was cooled to room temperature and filtered over a pad of celite. The filtrate was reduced in vacuo. The remaining brown residue was dissolvedin 6 M aqueous potassium hydroxide solution. The remaining solids were filtered off. The filtrate was cooled to 0 Cand neutralized by addition of concentrated aqueous HCl. Theproduct precipitated from the solution and was isolated by filtrationand washed with copious amounts of ice water and acetone(brown solid, 770 mg, 94%). 1H NMR (DMSO-d6) 6.35(bs, 2H, NH2), 7.49 (s, 1H, H-8), 10.04 (s, 1H, CHO), 10.72 (bs,1H, H-9), 11.96 (bs, 1H, H-1); 13C NMR (DMSO-d6) 98.36(C-7), 120.34 (C-8), 124.50 (C-5), 153.40 (C-2), 153.83 (C-4),159.02 (C-6), 185.47 (CHO). NMR data were recorded on aBruker AVANCE III with autosampler (1H NMR 300.36 MHz,13C NMR 75.53 MHz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,69205-79-4, its application will become more common.

Reference:
Article; Jung, Jihye; Czabany, Tibor; Wilding, Birgit; Klempier, Norbert; Nidetzky, Bernd; Journal of Biological Chemistry; vol. 291; 49; (2016); p. 25411 – 25426;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 38275-43-3, 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. 38275-43-3, name is 2-(Methylthio)pyrimidine-5-carbonitrile, molecular formula is C6H5N3S, 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 mixture of 2-(methylsulfanyl)pyrimidine-5-carbonitrile (25.00 g, 165.35 mmol, 1.00 eq) and hydroxylamine hydrochloride (22.98 g, 330.70 mmol, 2.00 eq) in ethanol (250.00 ml) and water (250.00 ml) was added sodium hydrogen carbonate (27.78 g, 330.70 mmol, 2.00 eq). The reaction was stirred at 70 C for 16 h. This mixture was filtered and washed with water (50 ml*4). The residue was collected and evaporated. This residue N’-hydroxy-2-(methylsulfanyl)pyrimidine-5- carboximidamide (29.00 g, crude) was used for next step without further purification

According to the analysis of related databases, 38275-43-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; BRUNET, Stephane; GOeRTZ, Andreas; GOURGUES, Mathieu; HILT, Emmanuelle; JAKOBI, Harald; NAUD, Sebastien; REBSTOCK, Anne-Sophie; DUCERF, Sophie; (78 pag.)WO2019/122323; (2019); 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,
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

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);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia