Day: July 14, 2021

Related Products of 4595-60-2, 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 4595-60-2, name is 2-Bromopyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Step 3: 2-(6-Bromopyridin-2-yl)pyrimidine Under argon, 54.5 ml (137.1 mmol) of a 2.5-molar solution of n-butyllithium (n-Buli) were diluted with 70 ml of THF. At a temperature of less than -70 C., 32.5 g (137.1 mmol) of 2,6-dibromopyridine, dissolved in 150 ml of THF, were added dropwise. The mixture was stirred for 15 min and, still at a temperature of less than -70 C., 9.2 ml (107 mmol) of a 5.6-molar solution of zinc chloride in diethyl ether were then added. The mixture was allowed to thaw, and a solution of 17.4 g (109 mmol) of bromopyrimidine in 50 ml of THF and a suspension of 3.9 g (3.4 mmol) of tetrakis(triphenylphosphine)palladium in 50 ml of THF were added. The mixture was boiled under reflux for 4 h, and after cooling Na-EDTA in water and dilute aqueous sodium hydroxide solution to pH=10 were added. The mixture was filtered off with suction to remove undissolved particles, the aqueous phase was extracted three times with ethyl acetate, the combined organic phases were dried with MgSO4 and the mixture was concentrated by evaporation.

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 4595-60-2, 2-Bromopyrimidine.

Reference:
Patent; Bayer CropScience AG; US2011/166143; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 16357-69-0, 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 16357-69-0 as follows.

Example 47A N-(5-Cyanopyrimidin-4-yl)-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboxamide At RT, 39.4 g (145 mmol) of 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid (preparation described in US2010/004235, page 27) were initially charged, and then thionyl chloride (370 ml) was added. The suspension was heated to reflux for 2 h and the now clear solution was concentrated under reduced pressure. 100 mg (0.345 mmol) of the acid chloride thus prepared were initially charged in pyridine (1.0 ml) and then 41.5 mg (0.345 mmol) of 4-amino-5-cyanopyrimidine were added in portions. The mixture was stirred at RT for 7 h and then left to stand overnight. Subsequently, volatile constituents were removed under high vacuum, the residue was separated by means of preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid gradient) and the product fractions were concentrated. This gave 30 mg (23% of theory) of the title compound in solid form. LC-MS (method 1): Rt=2.06 min MS (ESIpos): m/z=374 (M+H)+ 1H NMR (400 MHz, DMSO-d6): delta=5.91 (s, 2H), 7.14-7.20 (m, 1H), 7.22-7.33 (m, 2H), 7.35-7.42 (m, 1H), 7.49-7.54 (m, 1H), 8.57-8.62 (m, 1H), 8.73-8.77 (m, 1H), 9.28 (d, 2H), 11.64 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16357-69-0, its application will become more common.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Follmann, Markus; Stasch, Johannes-Peter; Redlich, Gorden; Ackerstaff, Jens; Griebenow, Nils; Knorr, Andreas; Wunder, Frank; Li, Volkhart Min-Jian; Baerfacker, Lars; Weigand, Stefan; US2014/148433; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 591-55-9, 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. 591-55-9, name is 5-Aminopyrimidine, molecular formula is C4H5N3, 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.

A solution of X-Phos (0.04 equiv) and Pd2(dba)3 (0.02 equiv) in toluene (15 vol) was bubbled with nitrogen and heated to 60 C for 15 min. (2S,4R)-1-(2-(3-acetyl-5-bromo-1H-indol-1-yl)acetyl)-4-fluoro-N-(4-phenylbutyl)pyrrolidine-2-carboxamide (1 equiv), 5- aniinopyriniidine (1.2 equiv) and sodium tert-butoxide (1.4 equiv) was added to the reaction mixture and the reaction mixture was heated to 100 C for 16 h. After completion of the reaction, the reaction mixture was quenched with water. The resulting mixture was extracted with ethyl acetate. The organic layer was separated, dried over anhydrous Na2S04, filtered and then concentrated. The residue was purified by column chromatography on silica gel using DCM/MeOH to give (2S,4R)-1-(2-(3-acetyl-5-(pyrimidin-5-ylamino)-1H-indol-1-yl)acetyl)-4-fluoro-N-(4-phenylbutyl)pyrrolidine-2-carboxamide. H NMR (400 MHz, DMSO-d6) delta 8.57 (s, 1H), 8.48 – 8.45 (m, 3H), 8.22 (s, 1H), 8.02 – 8.00 (m, 2H), 7.43 (d, J = 8.8 Hz, 1H), 7.19 – 7.05 (m, 5H), 5.56 – 5.32 (m, 2H), 5.15 (d, J= 17.1 Hz, 1H), 4.38 – 4.34 (m, 1H), 4.16 – 4.11 (m, 1H), 3.95 – 3.83 (m, 1H), 3.07 – 2.99 (m, 4H), 2.40 (s, 3H), 2.38 – 2.34 (m, 1H), 2.01 – 1.98 (m, 1H), 1.56 – 1.48 (m, 2H), 1.41 – 1.33 (m, 2H).

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 591-55-9, 5-Aminopyrimidine.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (319 pag.)WO2017/35351; (2017); 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. 18740-38-0, name is Thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione. A new synthetic method of this compound is introduced below., HPLC of Formula: C6H4N2O2S

Under a nitrogen streamThieno [2,3-d] pyrimidine-2,4 (1H, 3H) -dione (8.4 g, 50.0 mmol) and phosphoryl chlorideL), which was stirred for 3 hours at 106 C. After completion of the reaction, the organic layer was separated using ethyl acetateWater was removed using MgSO4. The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound2,4-dichlorothieno [2,3-d] pyrimidine (4.2 g, 20.5 mmol, yield 41%).

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, 18740-38-0, Thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione.

Reference:
Patent; Doosan Corporation; Kim, Hong Suk; Sim, Jae Uii; Kim, Tae Hyung; Lee, In Hyuk; La, Jong Gyu; Kim, Uhn Jin; Baek, Young Mi; (56 pag.)KR2015/36982; (2015); A;,
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

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

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