Tag: M.W:100-200

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

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

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

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;,
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

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

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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

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 52854-14-5, name is 4-Chloro-6-methoxy-5-nitropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 4-Chloro-6-methoxy-5-nitropyrimidine

b) 4-Methoxypyrimidin-5-amine10% Palladium on carbon (1 .10 g) was added to a solution of 4-chloro-6-methoxy-5- nitropyrimidine (Preparation 76a, 1 .97 g, 10.4 mmol) in ethanol (80 mL) and the reaction mixture was stirred at ambient temperature overnight under a hydrogen atmosphere at a pressure of 2 bars. The mixture was then filtered through Celite and the filter cake was washed with ethanol. The combined filtrate and washings were concentrated to give the title compound (1 .30 g, 100%) as a solid.LRMS (m/z): 126 (M+1 )+.1H NMR delta (300 MHz, DMSO-d6): 4.1 1 (s, 3H), 7.91 (s, 1 H), 8.59 (s, 1 H).

With the rapid development of chemical substances, we look forward to future research findings about 52854-14-5.

Reference:
Patent; ALMIRALL, S.A.; EASTWOOD, Paul Robert; GONZALEZ RODRIGUEZ, Jacob; GOMEZ CASTILLO, Elena; BACH TANA, Jordi; WO2012/160030; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 675-11-6, 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. 675-11-6, name is 4,6-Difluoropyrimidin-2-amine. A new synthetic method of this compound is introduced below.

EXAMPLE 9 Preparation of 2-amino-6-(4-chlorophenoxy)-4-fluoropyrimidine (Variant A) STR17 2.52 g (0.038 mol) of 85% sodium hydroxide were dissolved in 50 ml of methanol, 4.9 g (0.0382 mol) of 4-chlorophenol were added, and the mixture was evaporated to dryness. The residue of salt obtained in this way was taken up in 50 ml of N-methyl-2-pyrrolidone and, at 25 C., 5.0 g (0.0382 mol) of 2-amino-4,6-difluoropyrimidine were added, and the mixture was stirred at 140 C. for 4 hours. After the reaction mixture had been cooled to 25 C. it was stirred into 500 ml of water, and the resulting precipitate was isolated. 7.4 g (81% of theory) of the title compound of melting point 223-226 C. were obtained in this way.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,675-11-6, 4,6-Difluoropyrimidin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; BASF Aktiengesellschaft; US5011927; (1991); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia