Pyrimidines

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;,
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Related Products of 75833-38-4, 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 75833-38-4 as follows.

To 2-chloropyrimidine-4-carbonitrile [2.5 g, prepared by the procedure of Daves et. al. (J. Het. Chem. 1964, 1, 130-132)] in EtOH (250 ml) under N2 was added Boc2O (7.3 g). After the mixture was briefly placed under high vacuum and flushed with N2, 10% Pd/C (219 mg) was added. H2 was bubbled though the mixture (using balloon pressure with a needle outlet) as it stirred 4.2 h at RT. After filtration through Celite, addition of 1.0 g additional Boc2O, and concentration, the residue was purified by silica gel chromatography (5:1 – 4:1 hexanes/EtOAc) to obtain N-Boc-(2-chloropyrimidin-4-yl)-methylamine.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,75833-38-4, its application will become more common.

Reference:
Patent; Amgen Inc.; US2003/225106; (2003); A1;,
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Pyrimidine – Wikipedia

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. 29274-24-6, name is 5-Chloropyrazolo[1,5-a]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H4ClN3

To benzyl (7S)-7-methyl-5-(2-(2H-1,2,3-triazol-2-yl)benzoyl)-1,2,5-oxadiazepane-2-carboxylate (4.4 g) obtained in Step A of Example 2 was added 5.1M hydrogen bromide acetic acid solution (30 mL), and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated under reduced pressure, to a solution of the residue in 2-propanol (40 mL) was added 4-chloro-2,6-dimethylpyrimidine (2.23 g), and the mixture was stirred at 70 C. for 10 hr. The reaction mixture was cooled to 0 C., saturated aqueous sodium hydrogencarbonate solution was added thereto, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate), and crystallized (heptane/ethyl acetate) to give the title compound (2.30 g). 1H NMR (300 MHz, DMSO-d6) delta 1.02-1.50 (3H, m), 2.16-2.46 (6H, m), 2.95-3.29 (1H, m), 3.40-3.75 (3H, m), 3.79-4.74 (3H, m), 6.31-6.77 (1H, m), 7.05-8.30 (6H, m). MS: [M+H]+ 394.1. d value (or d-spacing) of specific peak in powder X-ray diffraction pattern=15.5, 7.9, 7.7, 7.4, 6.5, 5.6, 5.1, 4.3, 4.0, 3.67, 3.62, 3.57, 3.52 A. The title compound (11.4 mg) was obtained using ((7S)-7-methyl-1 ,2,5-oxadiazepan-5-yl)(2-(2H- 1 ,2,3-tri- azol-2-yl)phenyl)methanone hydrobromide (60 mg) obtained in Step A of Example 92 and 5-chloropyrazolo[1, 5-a]pyrimidine (26.1 mg) obtained in Reference Example 24 in the same manner as in Step B of Example 2. MS: [M+H]+405.1.

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, 29274-24-6, 5-Chloropyrazolo[1,5-a]pyrimidine.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KAMEI, Taku; ARIKAWA, Yasuyoshi; OHASHI, Tomohiro; IMAEDA, Toshihiro; FUJIMORI, Ikuo; MIKI, Takashi; YONEMORI, Jinichi; OGURO, Yuya; SUGIMOTO, Takahiro; SETO, Masaki; NISHIDA, Goushi; KAMATA, Makoto; IMOTO, Hiroshi; (132 pag.)US2018/155333; (2018); A1;,
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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.1780-32-1, name is 2,4-Dichloro-5,6-dimethylpyrimidine, molecular formula is C6H6Cl2N2, molecular weight is 177.03, as common compound, the synthetic route is as follows.Formula: C6H6Cl2N2

After 1-methoxymethyl-1,2,3,4-tetrahydroisoquinolin(0.5 g, 2.82 mmol) and triethylamine(0.4 ml, 2.82 mmol) were added to a suspension of 5,6-dimethyl-2,4-dichloropyrimnidine(0.48 g, 2.68 mmol) in dimethylformamide (5 ml), 0.5 g of the titled compound was obtained in accordance with the same procedure as in Step 1 of Example 35.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1780-32-1, 2,4-Dichloro-5,6-dimethylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Yuhan Corporation; US6352993; (2002); B1;,
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;,
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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

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

Adding a certain compound to certain chemical reactions, such as: 1753-48-6, 2-Aminopyrimidine-5-carbonitrile, 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: C5H4N4, blongs to pyrimidines compound. Formula: C5H4N4

Step A. Preparation of 2-chloropyrimidine-5 -carbonitrile[00222] To a stirring solution of 2-aminopyrimidine-5 -carbonitrile (1.0 g, 8.33 mmol) in CH3CN (15 ml) at room temperature under argon was added copper (II) chloride (1.679 g, 12.5 mmol) and tert-butyi nitrite (1.288 g, 12.5 mmol). The reaction mixture was placed in a preheated oil bath (60 0C) under Argon. The reaction mixture was cooled to room temperature and 20 ml of ether was added. The resulting insoluble material was filtered and the filtrate was concentrated. The crude product was dissolved in a small amount of DCM (~2 ml) and loaded onto a 40 g ISCO silica gel column which was eluted with a 20 min gradient from 0% to 100% EtOAc/Hexanes. 723 mg (61%) of 2-chloropyrimidine-5-carbonitrile was obtained as a tan solid. 1H NMR (400 MHz, CDCl3) delta ppm 8.90 (s, 2 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1753-48-6, 2-Aminopyrimidine-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WACKER, Dean, A.; ROSSI, Karen, A.; WANG, Ying; WU, Gang; WO2010/9183; (2010); 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;,
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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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