Tag: M.W:200-300

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. 5909-24-0, name is Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Formula: C8H9ClN2O2S

In THF (150 mL) was suspended 3-chloro-4-methoxybenzylamine hydrochloride salt (16.0 g, 76.9 mmol). The suspension was cooled in an ice bath, and triethylamine (19.4 g, 192.3 mmol) was added dropwisely. The reaction mixture was stirred at ambient temperature for 15 min, then was added ethyl 4-chloro-2-thiomethyl-5-pyrimidine carboxylate (14.9 g, 64.1 mmol). The reaction mixture was stirred at ambient temperature overnight. TLC was used to monitor the reaction. After the completion of the reaction, the solvent was removed by rotary evaporation. Acetic ether (500 mL) and water (200 mL) were added. The organic phase was separated, washed with hydrochloric acid (1N), saturated aqueous solution of sodium bicarbonate and brine, dried over sodium sulfate and filtrated. The filtrate was concentrated under reduced pressure. The solvent was removed by rotary evaporation to give oil. Methanol (100 mL) was added to precipitate a large amount of white solid. The mixture was filtrated and the solid was dried in vacuum to give ethyl 4-((3-chloro-4-methoxybenzyl)amine)-2-thiomethyl-5-pyrimidine carboxylate (21 g, 74.2 % yield).

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, 5909-24-0, Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; WU, Frank; WANG, Aichen; EP2886540; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 13162-43-1 ,Some common heterocyclic compound, 13162-43-1, molecular formula is C5H3Cl2N3O2, 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.

A solution of 4,6-dichloro-2-methyl-5-nitropyrimidine (3; J. Chem. Soc. 1954, 3836) (2.23 g, 11 mmol) in EtOH (30 mL) at -30 C. was treated with 1-ethylpropylamine (870 mg, 10 mmol) in EtOH (8 mL) and the reaction mixture was stirred at -30 C. for 1 hour and then warmed to ambient temperature. Volatiles were evaporated and the residue was partitioned between water and EtOAc. The organic layer was dried (sodium sulfate), evaporated, purified by flash chromatography (silica) to give compound (4).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13162-43-1, its application will become more common.

Reference:
Patent; Neurocrine Biosciences, Inc.; US6348466; (2002); B1;,
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. 13544-44-0, name is 2,4-Dichloro-5-iodopyrimidine, the common compound, a new synthetic route is introduced below. Quality Control of 2,4-Dichloro-5-iodopyrimidine

1-1 (20 g) was coupled to 1-2 in the presence of K2CO3 in DMAc at 80 oC overnight to afford 1-3. After purification, 25 g of crude 1-3 was obtained.1-3 (15 g) was converted to 1-5 in the presence of 1-4 using (PPh3)2PdCl2, CuI and TEA in THF at 40 oC for 4 hours. After purification, 9.3 g of crude 1-5 was obtained.1-5 (9.3 g) was converted to 1-6 using TBAF in THF at 60 oC for 4 hours.1-6 (5.6 g) was converted to 1-7 using HOAc in THF/H2O at 60 oC for 6 hours. After purification, 3.5 g of 1-7 was obtained.1-7 (1.2 g) was converted to 1-8 using TFA in DCM and stirring at room temperature for 1 hour. After purification, 410 mg of 1-8 was obtained.1-8 (25 mg) was coupled to 1-9 to afford 1-10 using TEA in EtOH and refluxing for 48 hours. After purification, 3.2 mg of 1-10 was obtained. 1-10 was converted to Compound 1 using TFA in DCM. Synthesis

The synthetic route of 13544-44-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; G1 THERAPEUTICS, INC.; STRUM, Jay Copeland; (151 pag.)WO2019/222521; (2019); A1;,
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Pyrimidine – Wikipedia

Related Products of 71406-78-5, 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 71406-78-5, name is Ethyl 4-amino-2-chloropyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

A solution of commercially available ethyl 4-amino-2-chloro-pyrimidine-5-carboxylate (500 mg, 2.48 mmol) and potassium carbonate (686 mg, 4.96 mmol) in a mixture of 1 ,4-dioxane (10 ml_) and water (2 ml_) was de-gassed via nitrogen sparging for 10 mins. Pd(dppf)Cl2 (1330) CH2CI2 (203 mg, 0.25 mmol) was added followed by commercially available (2- fluorophenyl)boronic acid (521 mg, 3.72 mmol) and placed under an atmosphere of nitrogen. The resulting mixture was stirred at 100 C for 2.75 hours. The mixture was allowed to cool, partitioned between DCM (50 ml_) and water (50 ml_), the layers separated and the aqueous portion further extracted with DCM (50 ml_). The combined organic portions were dried over MgSCU and the solvent removed in vacuo. Purification by column chromatography on silica eluting with a gradient of 10 to 30% EtOAc in petrol afforded the titled compound as a cream solid. (1331) LC-MS (Method 3B): Rt 1.62 mins; MS m/z 262.1 = [M+H]+ (1332) 1 H NMR (500 MHz, Chloroform-d) d 9.03 (s, 1 H), 8.00 (td, J = 7.8, 1.8 Hz, 1 H), 7.89 (s, (1333) 1 H), 7.44 (dddd, J = 8.3, 7.4, 4.9, 1.9 Hz, 1 H), 7.24 (td, J = 7.6, 1.2 Hz, 1 H), 7.17 (ddd, J = 11.2, 8.3, 1.1 Hz, 1 H), 5.78 (s, 1 H), 4.40 (q, J = 7.1 Hz, 2H), 1.41 (t, J = 7.1 Hz, 3H)

According to the analysis of related databases, 71406-78-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ADORX THERAPEUTICS LIMITED; MCCARTHY, Clive; MACLEOD, Calum; MOULTON, Ben; LENAGH-SNOW, Gabriel; (190 pag.)WO2019/122932; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 31169-27-4, 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 31169-27-4 as follows.

7-Bromo-4-methoxythieno[3,2-d]pyrimidine (193): To a suspension of sodium methoxide (4.33 g, 80.0 mmol) in dioxane (32 mL) under N2, was added 7-Bromo-4-chloro-thieno[3,2-d]pyrimid-4-one (192, 4.30 g, 16.0 mmol) as a solid in one portion. The reaction mixture was stirred at room temperature for 12 hours followed by removal of the solvent by rotary evaporation. The resulting residue was diluted with water and then extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to yield 7-bromo-4-methoxythieno[3,2-d]pyrimidine (2.07 g, 53percent) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,31169-27-4, its application will become more common.

Reference:
Patent; Thrash, Thomas; Cabell, Larry A.; Lohse, Daniel; Budde, Raymond J.A.; US2006/4002; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 905856-70-4, 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. 905856-70-4, name is 2-Bromo-5-iodopyrimidine, molecular formula is C4H2BrIN2, 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.

2-Bromo-5-iodopyrimidine (1.2 g, 4.2 mmol) was dissolved under nitrogen in 25 ml THF. Bis- (triphenylphosphine)-palladium(II)dichloride (300 mg, 420 muiotaetaomicron, 0.1 equiv.),ethynyltrimethylsilane (540 mg, 0.77 ml, 5.48 mmol, 1.3 equiv.), triethylamine (0.85 g, 1.17 ml, 8.4 mmol, 2 equiv.) and copper(I)iodide (40 mg, 210 muiotaetaomicron, 0.05 equiv.) were added and the mixture was stirred for 4 hours at 50C. The reaction mixture was cooled and evaporated to dryness. The crude product was purified by flash chromatography on silica gel, eluting with an ethyl acetate: heptane gradient 0: 100 to 40:60. The desired 2-bromo-5-trimethylsilanylethynyl- pyrimidine (0.75 g, 70 % yield) was obtained as a yellow solid, MS: m/e = 255/257 (M+H+).

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 905856-70-4, 2-Bromo-5-iodopyrimidine.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GREEN, Luke; GUBA, Wolfgang; JAESCHKE, Georg; JOLIDON, Synese; LINDEMANN, Lothar; RICCI, Antonio; RUEHER, Daniel; STADLER, Heinz; VIEIRA, Eric; WO2011/128279; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 90213-67-5 ,Some common heterocyclic compound, 90213-67-5, molecular formula is C7H5Cl2N3, 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.

(2S,3S)-3-Aminobicyclo[2.2.2]octane-2-carboxylic acid ethyl ester hydrochloride(1.26g, 5.40mmol)And 2,4-dichloro-7-methyl-7H-pyrrole[2,3-d]pyrimidine (1.10 g, 5.40 mmol) was dissolved in DMF (5 mL).Add K2CO3 (1.50g, 11.00mmol),The resulting mixture was stirred at room temperature overnight.Water (50 mL) was added to the reaction solution to quench the reaction.The liquid was separated and the aqueous phase was extracted with ethyl acetate (50 mL×2).The combined organic phases were washed with brine (80 mL).Dry with anhydrous sodium sulfate, filter, and distill off the solvent under reduced pressure.The residue was purified by silica gel column chromatographyThe title compound was obtained as a yellow solid (979 mg, 50%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,90213-67-5, its application will become more common.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ren Qingyun; Tang Changhua; Yin Junjun; Yi Kai; Lei Yibo; Wang Yejun; Zhang Yingjun; (138 pag.)CN108276401; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 926663-00-5, 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.926663-00-5, name is Ethyl 5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxylate, molecular formula is C9H9N3O3, molecular weight is 207.19, as common compound, the synthetic route is as follows.

B) ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate Ethyl 5-hydroxypyrazolo[1,5-a]pyrimidine-3-carboxylate (18.0 g) was suspended in acetonitrile (40 mL), phosphorus oxychloride (40 mL) was added at room temperature, and the mixture was stirred under a nitrogen atmosphere at 110 C. for 4 hr. The reaction mixture was cooled, and concentrated under reduced pressure. The residue was diluted with ethyl acetate and neutralized with aqueous sodium bicarbonate solution, and insoluble material was filtered off with Celite. The organic layer of the filtrate was purified by a silica gel pad, and the solvent was evaporated under reduced pressure. The precipitated solid was washed with ethyl acetate/diisopropyl ether to give the title compound (14.1 g). The mother liquor was further concentrated under reduced pressure and the resulting solid was washed with ethyl acetate/diisopropyl ether to give the title compound (2.40 g). 1H NMR (300 MHz, CDCl3) delta 1.42 (3H, t, J=7.2 Hz), 4.43 (2H, q, J=7.2 Hz), 6.99 (1H, d, J=7.2 Hz), 8.56 (1H, s), 8.63 (1H, d, J=7.2 Hz).

Statistics shows that 926663-00-5 is playing an increasingly important role. we look forward to future research findings about Ethyl 5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxylate.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; Kawasaki, Masanori; Mikami, Satoshi; Nakamura, Shinji; Negoro, Nobuyuki; Ikeda, Shuhei; Nomura, Izumi; Ashizawa, Tomoko; Imaeda, Toshihiro; Seto, Masaki; Sasaki, Shigekazu; Marui, Shogo; Taniguchi, Takahiko; (130 pag.)US2016/159808; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 56686-16-9, 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 56686-16-9 as follows.

General procedure: To a stirred anhydrous THF containing 5-bromo-2,4-dimethoxypyrimidine (0.29g, 1.3mmol) was added dropwise a 2.5M n-BuLi/hexane solution (0.6mL, 1.4mmol) at 195K under argon atmosphere. After 30min, 8a (0.52g, 1.3mmol) was added and the reaction mixture was stirred for 2h at this temperature. The reaction was allowed to warm to room temperature and quenched by addition of water. The product was extracted with diethyl ether. Then the combined organic layers were dried over MgSO4, filtered and concentrated. Column chromatography on SiO2 with petroleum ether and ethyl acetate (v/v=6/1) as the eluent afforded 0.35g of 1o as a colorless solid in 52% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,56686-16-9, its application will become more common.

Reference:
Article; Liu, Hongliang; Pu, Shouzhi; Liu, Gang; Chen, Bing; Dyes and Pigments; vol. 102; (2014); p. 159 – 168;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 26830-94-4, 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. 26830-94-4, name is 2,6-Dichloropyrimidine-4-carbonyl chloride, molecular formula is C5HCl3N2O, 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 Compound 2 (26.13 g, 123.6 mmol) in Et20 (500 mL) was added a mixture of 0.5M NH3 in dioxane (250 mL, 125 mmol) and DIPEA (22 mL, 126 mmol) dropwise over 50 mm. After stirring at RT overnight the reaction mixture was concentrated in vacuo to give a residue that was purified by flash chromatography (5i02, 10-50% EtOAc/hexanes). The product obtained was triturated with 10 mL 10% EtOAc/hexanes andfiltered to give Compound 3 as an orange crystalline solid (9.74 g). Yield 41%1H NMR (400 MHz, DMSO-d6): oe 8.40 (br s, 1H), 8.16 (br s, 1H), 8.10 (s, 1H); LC/MS: nz/z= 192.2 [M+Hf (Calc: 191.4).

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 26830-94-4, 2,6-Dichloropyrimidine-4-carbonyl chloride.

Reference:
Patent; PURDUE PHARMA L.P.; TAFESSE, Laykea; PARK, Jae, Hyun; WO2015/123398; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia