Day: July 13, 2021

Synthetic Route of 1088994-22-2 ,Some common heterocyclic compound, 1088994-22-2, molecular formula is C12H10N2O2, 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.

General procedure: To a solution of 5-methyl-2-(pyrimidin-2-yl)benzoic acid(0.040 g, 0.19 mmol) in CHCl3 (1.5 mL) were added DIPEA(0.092 ml, 0.53 mmol), 43d (0.037 g, 0.15 mmol) and a solution of1-propanephosphonic acid cyclic anhydride (T3P, 1.7 mol/L inEtOAc, 0.30 ml, 0.52 mmol) at room temperature. After this mixturewas stirred at 60 C for 5 h, water was added, and the mixturewas extracted with CHCl3. The organic layer was washed withbrine, dried over Na2SO4, filtered, and concentrated under reducedpressure. The resulting residue was purified by preparative HPLC toobtain the titled compound 12 as a colorless amorphous (0.024 g,36% yield). HRMS (ESI/APCI dual) for C24H24FN6O2 [M+H]+, calcd:447.1939, found: 447.1923; LC-MS t = 0.87 min, [M+H]+ = 447.Please see the Supplementary data for pictures of 500 MHz 1Hand 125 MHz 13C NMR spectra in CDCl3 at 25 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1088994-22-2, its application will become more common.

Reference:
Article; Futamura, Aya; Nozawa, Dai; Araki, Yuko; Tamura, Yunoshin; Tokura, Seiken; Kawamoto, Hiroshi; Tokumaru, Yuichi; Kakihara, Sora; Aoki, Takeshi; Ohtake, Norikazu; Bioorganic and Medicinal Chemistry; vol. 25; 20; (2017); p. 5203 – 5215;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 7752-78-5, name is 5-Bromo-2-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 7752-78-5

c) 1-Isopropyl-3,3-dimethyl-6-(2-methylpyrimidin-5-yl)indolin-2-one Through a suspension of 1 -isopropyl-3 ,3 -dimethyl-6-(4,4,5 ,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)indolin-2-one (220 mg, 668 imol), 5-bromo-2-methylpyrimidine (139 mg, 802 imol) and 2Maqueous Na2CO3 solution (668 tl, 1.34 mmol) in dioxane (3.0 ml) was bubbled argon for 5 minutes. [1,1 ?-Bis(diphenylphosphino)ferroceneldichloropalladium(II), complex with dichloromethane (1:1) (27.3 mg, 33.4 imol) was added and argon was bubbled through again for 5 minutes. The reaction mixture was heated to 110 °C for 20 hous. The solvent was evaporated and the residue was purified by silica gel chromatography using EtOAc/ heptane as eluentfollowed by amino silica gel chromatography using EtOAc/ heptane as eluent. The titlecompound was obtained as off-white solid (115 mg).MS ESI (m/z): 296.3 [(M+H)j.1H NMR (CDC13, 300 MHz): oe = 8.83 (s, 2H), 7.32 (d, J=7.7 Hz, 1H), 7.23 – 7.15 (m, 1H), 7.12(d, J=1.4 Hz, 1H), 4.69 (spt, J=7.1 Hz, 1H), 2.81 (s, 3H), 1.52 (d, J=7.1 Hz, 6H), 1.39 (s, 6H).

With the rapid development of chemical substances, we look forward to future research findings about 7752-78-5.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BRUNNER, Daniela; HILPERT, Hans; KOLCZEWSKI, Sabine; LIMBERG, Anja; MALBERG, Jessica; PRINSSEN, Eric; RIEMER, Claus; SHANKAR, Bavani G.; STOLL, Theodor; WO2014/202493; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 5604-46-6 ,Some common heterocyclic compound, 5604-46-6, molecular formula is C5H3Cl2N3O, 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.

PRODUCTION EXAMPLE 5, METHOD A-5 2-Amino-6-chloro-4-[[(3-(2-phenylethyl)-1-hydroxymethyl-1-cyclobutyl)methyl]amino]-5-formylpyrimidine (compound No. 71) 1-Hydroxymethyl-3-(2-phenylethyl)-1-cyclobutylmethylamine (3.51 g, 0.016 mol) was dissolved in ethanol (60 ml), and 2-amino-4,6-dichloro-5-formylpyrimidine (3.07 g, 0.016 mol) and triethylamine (6 ml) were added, which was followed by reflux for 2 hours. The solvent was distilled away under reduced pressure and chloroform was added to the residue. The mixture was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure and the residue was purified by silica gel column chromatography (chloroform, later chloroform_methanol=100:1) to give pale-yellow crystals (2.4 g, 40.0%), m.p. 130-137 C. (ether).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5604-46-6, its application will become more common.

Reference:
Patent; Nippon Shoji Kaisha Ltd.; US6080750; (2000); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 95928-49-7, 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. 95928-49-7, name is Ethyl 2-hydroxypyrimidine-5-carboxylate, molecular formula is C7H8N2O3, 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.

Step 4:Ethyl 2-chloropyrimidine-5-carboxylateEthyl 2-oxo-1,2-dihydropyrimidine-5-carboxylate (100 g, 0.59 mol) was slurried in POCl3 (600 mL) and cooled in an ice/water bath.The reaction mixture was heated to reflux temperature (oil-bath, T=117° C.) for 2 h.The light-brown colored homogeneous reaction mixture was cooled and the excess of POCl3 was removed by vacuum distillation.The semisolid brown residue was cooled (ice-water bath), toluene (400 mL) and a mixture of water (400 mL) and ice (200 g) were added.The mixture was stirred for 2 h and filtered.The organic phase was separated, dried and concentrated to dryness on a rotary evaporator.The dark yellow residue was purified by flash chromatography (SiO2, heptane/ethyl acetate 9/1) to afford the title compound.1H NMR (500 MHz, DMSO-d6): delta 9.18 (s, 2H); 4.38 (q, 2H); 1.34 (t, 3H).

According to the analysis of related databases, 95928-49-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Leclerc, Jean-Philippe; Li, Chun Sing; Ramtohul, Yeeman K.; US2011/152295; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 13627-49-1, 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 13627-49-1, name is 2-Methylpyrimidine-4-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

2-methylpyrimidine-4-carboxylic acid (250 mg, 1.810 mmol) was slurried in N,N,Dimethylformamide (dry) (3 ml). DIPEA (0.378 ml, 2.172 mmol) was added followed by HATU (757 mg, 1.991 mmol). After 15 mins 2-chloroaniline (0.191 ml, 1.810 mmol) was added to the brown suspension and the resulting reaction mixture stirred further at room temperature overnight. The reaction mixture was evaporated (55C to half volume (~4ml). This mixture was added to a cold water/ sat. sodium bicarbonate mixture (2:1, 20 ml). The solvents were filtered and the residue was taken in DCM. The organic layer was dried with Na2SO4, filtered and the filtrate was evaporated to dryness to give the product as a beige solid. Used as such.

According to the analysis of related databases, 13627-49-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; OSLO UNIVERSITY HOSPITAL HF; FORSCHUNGSVERBUND BERLIN E.V.; UNIVERSITY OF OULU; KRAUSS, Stefan; NAZARE, Marc; ANUMALA, Upendra Rao; LEHTIO, Lari; WAALER, Jo; HOLSWORTH, Dan; WEGERT, Anita; LEENDERS, Ruben Gerardus George; (99 pag.)WO2018/118868; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 335654-06-3, 2-Chloro-7H-pyrrolo[2,3-d]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, Formula: C6H4ClN3, blongs to pyrimidines compound. Formula: C6H4ClN3

To a stirred solution of 2-chloro-7H-pyrrolo[2,3-d]pyrimidine (20 g, 130 mmol) in DMF (300 mL) was added NBS (27.8 g, 156 mmol) at 0 oC under nitrogen atmosphere. The resulting solution was stirred for 2 h at room temperature. The resulting solution was poured into ice/water (1000 mL). Solid was precipitated and filtered. The filter cake was dried in a vacuum oven at room temperature to afford 5-bromo-2-chloro-7H-pyrrolo[2,3-d]pyrimidine (30 g, 99%) as a white solid. 1H NMR (400 MHz, DMSO-d6) d 12.79 (br s, 1H), 8.86 (s, 1H), 7.90 (d, J = 2.5 Hz, 1H). LC/MS (ESI, m/z): [(M + 1)]+ = 231.95, 233.90, 235.95

At the same time, in my other blogs, there are other synthetic methods of this type of compound,335654-06-3, 2-Chloro-7H-pyrrolo[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; KYMERA THERAPEUTICS, INC.; JI, Nan; MAINOLFI, Nello; WEISS, Matthew; (977 pag.)WO2020/10210; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 43212-41-5 ,Some common heterocyclic compound, 43212-41-5, molecular formula is C5H4Cl2N2O, 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 mixture of 2,4-dichloro-6-methoxypyrimidine (560mg, 3.1mmol), S-2-[3-(pyrimidin-2-yl)isoxazol-5-yl]pyrrolidine (680mg, 3.1mmol) and DIPEA (1.1ml, 6.3mmol) in 2-propanol (25ml) was heated at 120C for 18 hours. The volatiles were removed by evaporation and the residue purified by column chromatography on silica gel eluting with EPO EtOAc/hex (45:55) to give S-4-chloro-6-methoxy-2-{2-[3-(pyrimidin-2-yl)isoxazol-5- yl]pyrrolidin-l-yl}rhoyrimidine (600mg, 53%); m/z 359 [MH]+.

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. 43212-41-5, 2,4-Dichloro-6-methoxypyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/31745; (2007); 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. 131860-97-4, name is (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate. A new synthetic method of this compound is introduced below., Quality Control of (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate

A solution of the above (E) -2- [2- (6-chloropyrimidin-4-yloxy) phenyl] -3-methoxypropenoate in toluene Poured into 500mL three-necked reaction flask, 15.0 g (95%, 0 · 12 mol) of salicylonitrile was added, 10.7 g of sodium carbonate (99% (L) was stirred, heated to 90-95 C for 5 h, and the HPLC analysis showed that (Epsilon) -2- [2- (6-chloropyrimidin-4-yloxy) phenyl] -3 The reaction mixture was cooled to room temperature, filtered and the solid was washed twice with 50 mL of toluene. The filtrate and the washing solution were combined. The toluene was recovered by distillation under reduced pressure, 70 mL of methanol was added, stirred and cooled to 5-KTC , Crystallization, filtration, filter cake with 20mL methanol washing twice, drying, weight 36.7g, content 98.2%, yield 89.4%.

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, 131860-97-4, (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate.

Reference:
Patent; Chongqing Ziguang International Chemical Co., Ltd.; Ding Yongliang; Liu Jia; Zhang Fei; You Huan; Wu Chuanlong; Jin Haiqin; Zheng Daomin; Yao Rujie; (15 pag.)CN104230822; (2017); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application 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.

A suspension of tert-butyl 4-(((trifluoromethylsulfonyl)oxy)piperidine-1-carboxylate (6.2 g, 21.1 mmol), 2-chloropyrimidin-5-ol (2.5 g, 19.2 mmol) and potassium carbonate ( 13.3 g, 96 mmol) in dimethylsulfoxide (100 mL) was stirred at llOoC for 16 hours. The reaction mixture was cooled to room temperature and dimethylsulfoxide was distilled off under reduced pressure. The residue was then treated with water (50 mL) and precipitate was formed, filtered off and purified by column chromatography eluting with hexanes: ethyl acetate mixture (3:2) by volume to afford the title compound (2.0 g, 31.7 %) as a white crystalline powder:

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; Peu Lama Na Perm Syutikeolseu In Keu .; Man Su-reu-ta-rek-su-ha-il; Cha Pi-beu-mi-ka-il; Yu Din-mi-ka-il; Ge Jen-cheu-be-i-yu-ri; Ni Ki-tin-al-rek-san-deu-reu; (190 pag.)KR2019/15535; (2019); A;,
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. 28485-17-8, name is 5-Carbethoxyuracil. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 5-Carbethoxyuracil

A dry reaction flask equipped with a stirring bar and a reflux condenser was charged with 5-ethoxycarbonyluracil (1.84 g, 10 mmol), POCl3 (10 mL) and N,N-dimethylaniline (1 mL) and heated at 90 C. for 2 h. The excess POCl3 was removed under a reduced pressure and quenched with ice-water (100 g). The aqueous solution was extracted with ethyl ether (3×100 mL), washed with saturated aqueous NaHCO3 solution and water (100 mL, each). After drying over sodium sulfate, the ethyl ether was removed and the residue was dried under a high vacuum to afford 2,4-dichloro-5-ethoxycarbonylpyrimidine. 1H NMR (CDCl3): delta 9.00 (s, 1H), 4.45 (q, 2H, J=6.9 Hz), 1.42 (t, 3H, J=6.9 Hz).

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, 28485-17-8, 5-Carbethoxyuracil.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; Singh, Rajinder; Argade, Ankush; Payan, Donald; Molineaux, Susan; Holland, Sacha; Clough, Jeffrey; Keim, Holger; Bhamidipati, Somasekhar; Sylvain, Catherine; Li, Hui; Rossi, Alexander; US2015/266828; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia