Tag: M.W:100-200

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

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

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

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

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

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

Application of 2927-71-1, 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.2927-71-1, name is 2,4-Dichloro-5-fluoropyrimidine, molecular formula is C4HCl2FN2, molecular weight is 166.9685, as common compound, the synthetic route is as follows.

A solution of HOAc (2.4 g, 0.04 mol) in THF (15 mL) was added drop wise to a refluxing mixture of dichloro-5-fluoro-pyrimidine (3.34 g, 0.02 mol) and Zn (7.8 g, 0.02 mol) in THF (40 mL) over a 1-hour period. The mixture was refluxed for another 9 h. After cooling to room temperature, the solution was filtered to remove an insoluble solid. The solution containing 2-chloro-5-fluoro-pyrimidine was used directly in the next step reaction.

Statistics shows that 2927-71-1 is playing an increasingly important role. we look forward to future research findings about 2,4-Dichloro-5-fluoropyrimidine.

Reference:
Patent; Kalypsys, Inc.; US2005/234046; (2005); 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. 3177-24-0, name is 2,4-Dichloropyrimidine-5-carbonitrile. A new synthetic method of this compound is introduced below., COA of Formula: C5HCl2N3

Intermediate 14: Ethyl 3-[3-({[4-chloro-5-cyanopyrimidin-2-yllamino}methyl)-2- methylphenyllbenzoate:2,4-Dichloro-pyrimidine-5-carbonitrile (50 mg, 0.287 mmol, 1 .0 eq) was dissolved in DMF (1 ml) and intermediate 7 (77 mg, 0.287 mmol, 1.0 eq) was added to the solution, followed by DIEA (51 ul, 0.287 mmol, 1 .0 eq). The reaction mixture was stirred for 1 hour at room temperature, diluted with EtOAc (50 ml) and washed with water (50 ml x4). The organic fraction was dried over anhydrous Na2S04, filtrated and concentrated under reduced pressure and purified by preparative HPLC to yield the desired intermediate 14.

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, 3177-24-0, 2,4-Dichloropyrimidine-5-carbonitrile.

Reference:
Patent; AMAKEM NV; LEYSEN, Dirk; DEFERT, Olivier; BOLAND, Sandro; WO2012/156467; (2012); 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. 5993-98-6, name is 4-Chloro-2-methyl-6-(trifluoromethyl)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 4-Chloro-2-methyl-6-(trifluoromethyl)pyrimidine

To benzyl (7S)-7-methyl-5-(2-(1,3-thiazol-2-yl)benzoyl)-1,2,5-oxadiazepane-2-carboxylate (88 mg) obtained in Step A of Example 84 was added 5.1M hydrogen bromide acetic acid solution (2.0 mL), and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated under reduced pressure, and a mixture of the residue, ethanol (2.0 mL), acetic acid (0.012 mL) and 4-chloro-2-methyl-6-trifluoromethylpyrimidine (43.5 mg) was stirred in a microwave reactor at 150 C. for 0.5 hr. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate solution, 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 (hexane/diisopropyl ether) to give the title compound (45 mg). MS: [M+H]+ 464.0.

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, 5993-98-6, 4-Chloro-2-methyl-6-(trifluoromethyl)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

Related Products of 1224288-92-9, 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. 1224288-92-9, name is 5-Chloropyrazolo[1,5-a]pyrimidine-3-carbonitrile. A new synthetic method of this compound is introduced below.

To a mixture of 5-chloropyrazolo[1,5-ajpyrimidine-3-carbonitrile (40.00 mg, 223.99 umol, 1.00 eq) and 3- [(2R)-4,4-difluoropyrrolidin-2-ylj -5-fluoro-pyridine (61.62 mg, 223.99 umol, 1.00eq) in n-BuOH (2.00 mL) was added DIPEA (144.74 mg, 1.12 mmol, 5.00 eq). The resulting mixture was stirred at 100C for 16 hrs. The mixture was concentrated and the crude product was purified by acidic prep-HPLC (TFA system). (R)-5-(4,4-difluoro-2-(5-fluoropyridin-3 – yl)pyrrolidin- 1 -yl)pyrazolo [1 ,5-ajpyrimidine-3 -carbonitrile (48.70 mg, 85.09 umol, yield: 38%) was obtained as a brown solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1224288-92-9, its application will become more common.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; WENGLOWSKY, Steven, Mark; MIDUTURU, Chandrasekhar, V.; BIFULCO, Neil, Jr; KIM, Joseph, L.; (91 pag.)WO2017/87778; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia