Category: pyrimidines

Reference of 163263-91-0 , The common heterocyclic compound, 163263-91-0, name is 2,4-Dichloro-6-(4-methoxyphenyl)pyrimidine, molecular formula is C11H8Cl2N2O, 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 2,4-dichloro-6-(4-methoxyphenyl)pyrimidine (1.01 g, 3.92 mmol) and (+/-)-trans-methyl 3-aminobicyclo[2.2.2]octane-2-carboxylate (1.02 g, 5.88 mmol) in DMF (20 mL) was added potassium carbonate (0.81 g, 5.88 mmol), and the mixture was stirred at 50 C overnight. To the reaction mixture was added water (70 mL), and the resulting mixture was extracted with ethyl acetate (100 mL x 3). The combined organic layers were washed with saturated brine (150 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dry and the residue was purified by silica gel column chromatography (n-hexane/EtOAc (v/v) = 20/1-5/1) to give the title compound as a white solid (1.01 g, 64%).MS (ESI, pos. ion) m/z: 402.2 [M+H]?H NIVIR (400 MHz, CDC13) (ppm): 7.98 (d, J= 8.7 Hz, 2H), 6.98 (d, J= 8.9 Hz, 2H), 6.72 (s, 1H), 5.46 (d, J= 6.3 Hz, 1H), 4.32 (s, 1H), 3.88 (s, 4H), 3.74 (s, 3H), 2.39 (d, J= 5.1 Hz, 1H),2.08 (s, 1H), 1.90 – 1.84 (m, 1H), 1.78 – 1.71 (m, 2H), 1.70 – 1.63 (m, 4H), 1.58 (d, J= 10.2 Hz, 2H).

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

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; REN, Qingyun; TANG, Changhua; YIN, Junjun; YI, Kai; LEI, Yibo; WANG, Yejun; ZHANG, Yingjun; (215 pag.)WO2018/127096; (2018); 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.65754-04-3, name is 6-Oxo-1,6-dihydropyrimidine-5-carboxylic acid, molecular formula is C5H4N2O3, molecular weight is 140.1, as common compound, the synthetic route is as follows.name: 6-Oxo-1,6-dihydropyrimidine-5-carboxylic acid

A mixture of 4-hydroxy-5-pyrimidinecarboxylic acid (0.88 g, 6.3 mmol) in 5 drops of DMF and 6 mL of thionyl chloride was heated at reflux for 3 hours. The mixture was concentrated and the residue was dissolved in methylene chloride. A mixture of the residue, dimethylamine hydrochloride (0.62 g, 7.6 mmol) and triethylamine (4.5 mL, 31.5 mmol) in 50 mL of methylene chloride was stirred at 0 C. for 0.5 hours. The mixture was poured into water and aqueous sodium bicarbonate. The mixture was extracted with methylene chloride (2*30 mL) and the extract was washed with brine, dried (Na2 SO4) and concentrated by rotary evaporation to give 4-chloro-N,N-dimethyl-5-pyrimidinecarboxamide (0.66 g, 3.6 mmol) as an oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,65754-04-3, 6-Oxo-1,6-dihydropyrimidine-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Syntex (U.S.A.) Inc.; US5688795; (1997); A;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 54368-61-5, Ethyl 2,6-dichloro-5-nitropyrimidine-4-carboxylate, 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, 54368-61-5, blongs to pyrimidines compound. Recommanded Product: Ethyl 2,6-dichloro-5-nitropyrimidine-4-carboxylate

The product from step 2 (2.64 g) was HYDROGENATED at room temperature at a pressure of 3.75 bar hydrogen gas for 5 hours, in dioxane (180 ml) and in the presence of magnesium oxide (1.96 g) and 5% palladium on carbon (2.44 g). The reaction mixture was filtered through celite, washed with dioxane, ethyl acetate, and methanol. The solvents were combined and evaporated and the reaction mixture was purified by column chromatography on silica gel (40-60) eluting with ethyl acetate to give 5-amino-2-chloro-pyrimidine-4- carboxylic acid ethyl ester as a yellow solid (1. 38 g). IH NMR (CDCL3) 8 ppm : 1.45 (t, 3H), 4.5 (q, 2H), 5.75 (bs, 2H), 8.3 (s, LH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,54368-61-5, its application will become more common.

Reference:
Patent; SYNGENTA LIMITED; SYNGENTA PARTICIPATIONS AG; WO2004/56826; (2004); A1;,
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Pyrimidine – Wikipedia

Synthetic Route of 4214-85-1, 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 4214-85-1 as follows.

In a 100 mL two-neck round-bottom flask under N2 atmosphereand molecular sieve 3 A was added 2 (2.0 g, 11.7 mmol) in dry DMF (25 mL) and DMF dimethyl acetal (7.5 mL, 70.0 mmol). The mixturewas stirred at 100 C for 24 h and then cooled. The mixturewas dried under vacuum. Acetone (15 mL) was added and theformed precipitate was filtered and washed with acetone (10 mL)furnishing 3 in 96% yield (3.16 g)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4214-85-1, its application will become more common.

Reference:
Article; Rodrigues, Marili V.N.; Barbosa, Alexandre F.; Da Silva, Julia F.; Dos Santos, Deborah A.; Vanzolini, Kenia L.; De Moraes, Marcela C.; Correa, Arlene G.; Cass, Quezia B.; Bioorganic and Medicinal Chemistry; vol. 24; 2; (2016); p. 226 – 231;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 274-71-5, Pyrazolo[2,3-a]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, SDS of cas: 274-71-5, blongs to pyrimidines compound. SDS of cas: 274-71-5

Preparation of compound 23b: 3-(6-Chloro-pyrazin-2-yl)-pyrazolo[1,5- ajpyrimidineTo a stirred solution of 23a (30 g, 0.252 mol), 2-bromo-6-chloro-pyrazine (58.5 g, 0.302 mol) and PPh3 (6.6 g, 0.0252 mol) in dioxane (300 ml_) was added Cs2CO3 (82.1 g, 0.252 mol) and Pd(OAc)2 (11.3 g, 0.0504 mol). The mixture was purged with N2 x3 and stirred at reflux for 3 days. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated, and the resulting residue was purified via preparative HPLC which gave the title compound 23b as a yellow solid (3.01 g, 5%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,274-71-5, Pyrazolo[2,3-a]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; NINKOVIC, Sacha; BRAGANZA, John Frederick; COLLINS, Michael Raymond; KATH, John Charles; LI, Hui; RICHTER, Daniel Tyler; WO2010/16005; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 13877-55-9, Adding some certain compound to certain chemical reactions, such as: 13877-55-9, name is 7-Hydroxypyrazolo[4,3-d]pyrimidine,molecular formula is C5H4N4O, 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 13877-55-9.

Compound 28: DMF (1.05 mL) was added to a solution containing 27 (1.0 g, 7.3 mmol) in thionyl chloride (21 mL). Heated the stirring solution to 90 C. for 1 hour. Cooled the homogeneous reaction mixture to room temperature. Concentrated to remove volatiles and diluted the reaction mixture with EtOAc followed by ice. Extracted the aqueous layer with EtOAc. Combined the organics, washed with saturated NaHCO3, dried with MgSO4, filtered and concentrated to afford 28 (0.73 g, 64%), ES (+) MS m/e=155.

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. 13877-55-9, 7-Hydroxypyrazolo[4,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sunesis Pharmaceuticals, Inc.; US2007/27166; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 63155-11-3, Ethyl 2-(pyrimidin-2-yl)acetate, 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, name: Ethyl 2-(pyrimidin-2-yl)acetate, blongs to pyrimidines compound. name: Ethyl 2-(pyrimidin-2-yl)acetate

To a solution of ethyl 2-(pyrimidin-2-yl)acetate (Example 31b, 410 mg, 2.47 mmol)in ethanol (5 mL) was added 2N NaOH (2 mL) at room temperature under nitrogen. Thereaction mixture was stirred at room temperature under nitrogen for 72 hours, then5 concentrated under reduced pressure. The residue was triturated with ethanol andconcentrated under reduced pressure to give the title compound, which was carried onto thenext step without further purification. MS 139 (MH+).

The synthetic route of 63155-11-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SENOMYX, INC.; TACHDJIAN, Catherine; KARANEWSKY, Donald; WERNER, Sara; DARMOHUSODO, Vincent; YAMAMOTO, Jeff; WO2014/25706; (2014); A1;,
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Pyrimidine – Wikipedia

Application of 1126-44-9, 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. 1126-44-9, name is 2-Methylsulfanylpyrimidine-4-carboxylic acid, molecular formula is C6H6N2O2S, 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.

(c). 2-Methylsulfanyl-pyrimidin-4-yl)-methanol; At O0C oxalyl chloride (295 mul) was added to a solution of DMF (91.2 mul) in dichloromethane (2 ml). After stirring at O0C for 1 h, the reaction mixture was concentrated in vacuo. The residue was dissolved in acetonitrile (2 ml) and THF (3 ml), followed by portion wise addition of the product of example 21b (200 mg) at O0C in a nitrogen atmosphere. After stirring at O0C for 15 min, the reaction mixture was cooled (-780C) and 2M NaBH4 in DMF (590 mul) was added. After stirring at -2O0C for 3 h, the reaction mixture was quenched with 2N HCl and concentrated in vacuo. The residue was dissolved in water and the remaining solution was adjusted to pH 11 with 2N NaOH, followed by extraction with dichloromethane. The organic layer was separated, dried (MgSO4), filtered and concentrated in vacuo. Yield: 180 mg. MS-ESI: [M+H]+ = 156

According to the analysis of related databases, 1126-44-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; N.V. ORGANON; WO2006/117368; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 19858-50-5, (2-(Methylthio)pyrimidin-5-yl)methanol, 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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

To a solution of the above compound (0.19 g, 1.2 mmol) in 8.5 mL CH2CI2 was added thionyl bromide (0.1 1 mL, 1.5 mmol). The reaction was stirred at room temperature for 2.5 h and quenched with saturated aqueous ammonium chloride. The layers were separated, and the organic portion was washed with water and brine, dried over sodium sulfate, filtered, and concentrated to afford 5-(bromomethyl)-2-(methylsulfanyl)pyrimidine that gave a mass ion (ES+) of 221.1 (83/4Br) for M+H\

The synthetic route of 19858-50-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; SCHLEGEL, Kelly-Ann; YANG, Zhi-Qiang; WO2011/84368; (2011); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 959236-97-6, 4-Bromo-2-(methylthio)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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

A suspension of 4-bromo-2-(methylthio)pyrimidine (9 A, 1.18g, 7.35 mmol) , potassium carbonate (37ml, 0.4 M in water), o-tolylboronic acid (1 g, 7.35 mmol) andtetrakis(triphenylphosphine)palladium(0) (425 mg, 0.37 mmol) in DME (40 ml) was degassed for 20 minutes. It was then heated at reflux for 2 hours. The reaction mixture was cooled and filtered through celite. The filtrate was extracted with EtOAc (2 x 30 ml). The organic layer was dried with Na2S04, filtered and concentrated. The crude product was purified by flash column (Rf: 0.3 10%EtOAc/Hexanes). The yield was 98%. MS (m/z) 217 [M+H]+

The synthetic route of 959236-97-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; BONDY, Steven S.; CANNIZZARO, Carina E.; CHOU, Chien-hung; HALCOMB, Randall L.; HU, Yunfeng Eric; LINK, John O.; LIU, Qi; SCHROEDER, Scott D.; TSE, Winston C.; ZHANG, Jennifer R.; WO2013/6738; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia