Tag: M.W:100-200

Reference of 90213-66-4, 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.90213-66-4, name is 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H3Cl2N3, molecular weight is 188.01, as common compound, the synthetic route is as follows.

After 2,4-dicWoro-7H-pyrrolo[2,3-d]pyrimidine (3.0 g, 16.0 mmol) was dissolved in acetone (20.0 mL), 4- methylbenzenesulfonyl chloride (4.6 g, 23.9 mmol) was added thereto. After cooling to 0 C, 2 M sodium hydroxide solution (12.0 mL) was slowly added dropwise and then stirred at room temperature for 2 hours. The organic layer was isolated, treated with magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue was isolated by column chromatography to obtain a title compound (2.9 g, yield: 80.0%). [H NMR (500MHz,CD3OD) delta 8.12(d, 2H), 7.76(d, 1H), 7.37(d, 2H), 6.68(d, 1H), 2.43(s, 3H)

The chemical industry reduces the impact on the environment during synthesis 90213-66-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; DAEWOONG PHARMACEUTICAL CO., LTD.; KIM, In Woo; HAN, Mi Ryeong; YOO, Jakyung; OH, Yun Ju; KIM, Ji Duck; KIM, Nam Youn; JUN, Sun Ah; LEE, Jun Hee; PARK, Joon Seok; (197 pag.)WO2018/4306; (2018); 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. 58347-49-2, name is 7-Chloropyrazolo[1,5-a]pyrimidine. A new synthetic method of this compound is introduced below., Formula: C6H4ClN3

EXAMPLE 584-{7-Fluoro-8-methyl-3-r(l»S^-l-(pyrazolori,5-alpha1pyrimidin-7-ylamino’)ethyl]quinolin-2- yl I piperazine- 1 -carboxamide Intermediate 36 (50 mg, 0.151 mmol), 7-chloropyrazolo[l,5-alpha]pyrimidine (34.7 mg, 0.226 mmol), DIPEA (0.079 mL, 0.453 mmol) and n-BuOH (1 mL) were combined and heated under microwave irradiation at 1400C for 1 h. After cooling, the mixture was dissolved in EtOAc (100 mL) and washed with saturated brine (3 x 20 mL). The organic layer was separated, dried (MgSO4), filtered and concentrated in vacuo. Purification by preparative HPLC gave the title compound (7 mg, 10%) as a yellow solid. deltaH (DMSO-d6) 8.24 (d, J4.99 Hz, IH), 8.14 (s, IH), 8.10 (d, J2.33 Hz, IH), 7.70 (dd, J8.89, 6.22 Hz, IH), 7.25 (t, J9.13 Hz, IH), 6.58 (d, J7.55 Hz, IH), 6.51 (d, J2.33 Hz, IH), 6.40 (d, J 5.03 Hz, IH), 5.46 (s, 2H), 5.05 (t, J6.89 Hz, IH), 3.95-4.02 (m, 2H), 3.81-3.88 (m, 2H), 3.67-3.75 (m, 2H), 3.27-3.32 (m, 2H), 2.49 (d, J2.33 Hz, 3H), 1.29 (d, J6.59 Hz, 3H). LCMS (ES+) 449 (M+H)+, RT 2.59 minutes (Method 2).

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, 58347-49-2, 7-Chloropyrazolo[1,5-a]pyrimidine.

Reference:
Patent; UCB PHARMA S.A.; ALLEN, Daniel, Rees; BROWN, Julien, Alistair; BUeRLI, Roland; HAUGHAN, Alan, Findlay; LANGHAM, Barry, John; MATTEUCCI, Mizio; OWENS, Andrew, Pate; RAPHY, Gilles; SHARPE, Andrew; WO2010/133836; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 110099-94-0, 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 110099-94-0, name is 2-(Methylthio)pyrimidine-5-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of crude 19 (100 mg, 0.48 mmol ) in THF (5 mL) is added isobutyl chloroformate (0.05 mL, 0,58 mmol) followed by NMM (0.06 mL, 0.58 mmol) at – 10 C. After stirring for 10 minutes, the mixture is filtered and sodium borohydride (37 mg, 0,96 mmol) in water (0.2 mL) is added dropwise at 0 C. After stirring at room temperature for 20 minutes, the mixture is concentrated and the residue is partitioned between EA (20 mL) and water (10 mL). The organic layer is washed with brine (10 mL), dried over anhydrous sodium sulfate, concentrated, and purified by silica gel column chromatography (MeOH:DCM = 1 : 100) to give A38 as a colorless oil (50 mg, 74% yield). (MS: i 1 · 1 11 194.1 ).Following the procedure for A38 using 133 (1.18 g, 6.9 mmoi), NMM (695 mg.6.9 mmoi), THF (20 mL), isohutyl chioroformate (1.13 g. 8.25 mmol), sodium borodeuteride(289 mg, 6.9 mmoi), and deueterate water (0.5 mL), then purii with silica gel columnchromatography (EA:PE == 1:5) to give i13d2 as a light yellow solid (290 rng, 25%). (MS:[M+H] 159.1)

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 110099-94-0, 2-(Methylthio)pyrimidine-5-carboxylic acid.

Reference:
Patent; IMMUNE SENSOR, LLC; THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; ZHONG, Boyu; SUN, Lijun; SHI, Heping; LI, Jing; CHEN, Chuo; CHEN, Zhijian; (270 pag.)WO2017/176812; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 7431-45-0, Adding some certain compound to certain chemical reactions, such as: 7431-45-0, name is 2-Phenylpyrimidine,molecular formula is C10H8N2, 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 7431-45-0.

General procedure: To a dried Schlenk tube was equipped with a magnetic stirbar. [Cp*RhCl2]2 (0.005 mmol, 2.5 mol %, 3.1 mg), AgSbF6 (0.03 mmol, 15 mol %,10.3 mg), substrate 1 (0.2 mmol or 0.4 mmol), HOAc (1 ml), substrate 2 (0.24 mmolor 0.2 mmol) were added sequentially under argon. The tube was stirred at roomtemperature or 80 C for 12 h. After completion of the reaction, the mixture wasdiluted with EtOAc (10 mL), filtered through a short pad of silica gel and washedwith EtOAc (30 mL). The filtrate was pre-absorbed on silica gel and concentrated byrotary evaporation. The crude product was purified by flash silica gel (300-400 mesh)chromatography to afford the desired products product 3.

According to the analysis of related databases, 7431-45-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Duan, Chang-Lin; Liu, Xing-Yu; Tan, Yun-Xuan; Ding, Rui; Yang, Shiping; Tian, Ping; Lin, Guo-Qiang; Synlett; vol. 30; 8; (2019); p. 932 – 938;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 62846-82-6, 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 62846-82-6, name is Ethyl 4-pyrimidinecarboxylate. This compound has unique chemical properties. The synthetic route is as follows.

General Procedure 14 was followed in the preparation of Intermediate 21. 2149 General Procedure 14 2151 Intermediate 19 Intermediate 21 2152 [0246] Intermediate 19 (1.6 g, 10.5 mmol) was added dropwise to a vigorously stirring 2153 mixture of aminoguanidine sulfate (10.3 g, 42.1 mmol, 4 eq) in freshly prepared NaOMe 2154 (using 968 mg, 42.1 mmol of Na in 28 mL of dry MeOH) at 0 C. The resulting mixture was 2155 heated to reflux for 20 h. The mixture was then cooled to RT, carefully poured over ice cold 2156 water (20 mL) and concentrated in vacuo. The crude residue was purified over neutral 2157 alumina using 4-10% MeOH-CHCl3 as the eluent to give Intermediate 21 (5 OOmg, 26%) . 2158 MS: 163 [M + H]+; TLC: 20% MeOH in CHC13: Rf: 0.20.

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 62846-82-6, Ethyl 4-pyrimidinecarboxylate.

Reference:
Patent; VERSEON, INC.; SHORT, Kevin, Michael; PHAM, Son, Minh; WILLIAMS, David, Charles; KITA, David, Ben; WO2014/145986; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 17321-93-6 ,Some common heterocyclic compound, 17321-93-6, molecular formula is C5H6BrN3, 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.

[0244] To a dry 1 L flask was added 5-bromo-4-methylpyrimidine-2~ylamine(18.8 g, 100 mmol), potassium acetate (29.45 g, 300 mmol), 4,4,5,5-tetramethyl-2- (4,4,5 ,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l,3,2-dioxaborolane (26.7 g, 105 mmol) and dioxane (500 mL). Argon was bubbled through the solution for 15 minutes, at which time l,r-bis(diphenylphosphino)ferrocene palladium(II) chloride dichloromethane adduct (4.07 g, 5 mmol) was added. The reaction was refluxed in a 115 0C oil bath for 18 hours under argon. After cooling to room temperature, EtOAc (500 mL) was added and the resulting slurry was sonicated and filtered. Additional EtOAc (500 mL) was used to wash the solid. The combined organic extracts were washed with H2O (2×300 mL), NaCl(sat.) (30O mL), dried over Na2SO4, concentrated and purified by SiO2 chromatography (EtOAc eluent) yielding 18.1 g of an off-white solid. By 1H NMR the material was a 5:1 mixture of boronate ester and 4-methylpyrimidine-2-ylamine as a 7 001708byproduct. The material was used as is in subsequent Suzuki reactions. LCMS {m/z): 154 (MH+ of boronic acid, deriving from in situ product hydrolysis on LC). 1H NMR (CDCl3): delta 8.52 (s, IH), 5.14 (bs, 2H), 2.56 (d, 3H), 1.32 (s, 12H).

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. 17321-93-6, 2-Amino-5-bromo-4-methylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; WO2007/84786; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 4983-28-2, 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. 4983-28-2, name is 2-Chloro-5-hydroxypyrimidine, molecular formula is C4H3ClN2O, 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.

b) 7.2 g (59 mmol) R-2,2-difluoro-cyclopropanecarboxylic acid are added to 100 mL THF, chilled to 0°C and 35 mL (77 mmol) lithium aluminum hydride solution (2.2 M in 2-methyltetrahydrofuran) are added dropwise. The mixture is stirred at r.t. over night. After that the mixture is chilled to 0°C and quenched by the addition of 3 ml water and 3 ml aq. NaOH solution (c= 4 mol/L) slowly. The resulting mixture is stirred for 30 min, filtered, washed with THF and the filtrate is concentrated by evaporation. The residue is added to Et2O, dried over Na2SO4, filtered and the solvent is removed in vacuo. C4H4F2O(M= 108.1 g/mol) Rt (GC):15.4 min (method a) c) ) 2.16 g (20.0 mmol) of the above mentioned product, 2.75 g (20 mmol) 1-chloro-5- hydroxypyrimidine and 6.56 g (25 mmol) triphenylphosphine are added to 20 ml THF and cooled to 0 °C. Then 11.5 mL (25 mmol) diethylazocarboxylate (40 percent in toluene) are added carefully at constant temperature. Then cooling is removed and the mixture is stirred at r.t. for 3 h. Afterwards the solvent is removed in vacuo, diethylether is added and the mixture is filtered. The solvent is removed in vacuo and the residue is purified by flash chromatography (silica gel, PE/EtOAc) C8H7CIF2N2O (M= 220.60 g/mol) ESI-MS: 221 [M+Hf Rt (HPLC): 0.91 min (method I)

According to the analysis of related databases, 4983-28-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FLECK, Martin; HEIMANN, Annekatrin; HEINE, Niklas; NOSSE, Bernd; ROTH, Gerald Juergen; WO2014/170197; (2014); 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.5177-27-5, name is 5-Amino-2,4-dichloropyrimidine, molecular formula is C4H3Cl2N3, molecular weight is 163.9927, as common compound, the synthetic route is as follows.SDS of cas: 5177-27-5

To a mixture containing 2,4-dichloropyrimidin-5-amine (900 mg, 5 5 mmol), 4- ethynyl-l,2~dimethoxy benzene (980 mg, 6.0 mmol), copper(I) iodide (105 mg, 0 55 mmol) and Pd(Ph3P)4 (190 mg, 0 17 mmol) in a screw cap vial was added nitrogen gas purged TEA (15 mL). The vial was fitted with a Teflon lined septum cap. The system was evacuated under vacuum (via a needle from a mtrogen/vacuum manifold line) and backfilled with nitrogen gas. The needle was removed and the vial was heated at 100 C for 3 h. The reaction mixture was cooled to room temperature and concentrated. The resulting slurry was dissolved in THF/DCM/MeOH mixture and adsorbed to 10 g silica and transferred to an empty cartridge. The cartridge was fitted to a Teledyne ISCO CombiFlash Rf chromatography system and purified on a 24 g ISCO silica gel column which was eluted over a 15 min gradient with 5%-100% hexanes/EtOAc to afford 2- chloro-4-((3,4-dimethoxyphenyl)ethynyl)pyrimidin-5-amine (1.3 g, 4.5 mmol, 82 % yield), MS m/z (290, M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5177-27-5, 5-Amino-2,4-dichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DYCKMAN, Alaric J.; DODD, Dharmpal S.; MUSSARI, Christopher P.; WHITELEY, Brian K.; KUMAR, Sreekantha Ratna; RAMACHANDRA REDDY, Anupama Kandhi; (134 pag.)WO2019/126083; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 32779-36-5, 5-Bromo-2-chloropyrimidine, 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, 32779-36-5, blongs to pyrimidines compound. SDS of cas: 32779-36-5

A mixture of 5-bromo-2-chloropyrimidine (1 g, 5.18 mmol), dimethylamine hydrochloride (1.26 g, 15.6 mmol) and K2C03 (2.16 g, 15.6 mmol) in EtOH (15 mL) was heated to 120C for 16h. After cooling, the solvent was evaporated off and the residue was used for next step without further purification. LCMS (m/z): 202.1/203.1 [M+H]”7 [M+2H]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,32779-36-5, its application will become more common.

Reference:
Patent; EPIZYME, INC.; DUNCAN, Kenneth, W.; CHESWORTH, Richard; MUNCHHOF, Michael, John; JIN, Lei; WO2014/100695; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 3073-77-6, 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 3073-77-6, name is 2-Amino-5-nitropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 3. Synthesis of N-f4-(3-Pyrrolidin-l-vI-Propane-l-Sulfonvn-Phenvn- Pyrimidi?e-2,5-Diamine (Intermediate 2)[0127] To a solution of 2-amino-5-nitropyrimidine (840 mg, 6.0 mmol) in 50 mL anhydrous 1,4-dioxane were added l-[3-(4-bromo-benzenesulfonyI)-propyl]-pyrrolidine (2.9 g, 8.7 mmol), Xantphos, (690 mg, 1.2 mmol), Pd2(dba)3 (559 mg, 0.61 mmol) and CS2CO3 (5.8 g, 18 mmol). The reaction mixture was stirred at 1000C for 5 h under argon. The solvent was removed under reduced pressure. The resulting solution was extracted with CHCI3 (3 x 50 mL) and sat. NaHCO3 (50 mL). The organic layer was separated, washed with brine, dried over Na2SO4 and filtered. The organic solvent was removed and the crude product was purified by silica gel column with 20% CH3OH / CHCl3 as an eluent. The precipitated yellow solid was isolated by washed with acetone and dried in vacuo (1.2 g, 52%). The above product was hydrogenated in 100 mL methanol/ethyl acetate (v/v: 1:1) using Pd/C (10%, 1 g) for 2 h. The palladium catalyst was removed by filtration, and the solvent was evaporated. The pale yellow solid was isolated by washed with acetone/methanol (v/v 5:1) and dried in vacuo (550 mg, 49%).[0128] 1H NMR (DMSOd6): delta 1.60-1.68 (m, 6H), 2.10-2.35 (m, 4H), 2.40-2.50 (m, 2H), 3.05-3.25 (m, 2H)5 5.02 (br s, 2H), 7.68 (d, J= 9.0 Hz, 2H), 7.87 (d, J= 9.0 Hz, IH)5 8.02 (s, 2H), 9.68 (s, IH).

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 3073-77-6, 2-Amino-5-nitropyrimidine.

Reference:
Patent; TARGEGEN, INC.; WO2008/8234; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia