Pyrimidines

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. 22276-95-5, name is 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below., Recommanded Product: 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

To a solution of 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (E-2) (2.33 g, 10.0 mmol, 1.0 eq) in anhydrous THF (100 mL) at -78 C under argon, n-BuLi solution (2.5 M in THF, 8.8 mL, 22.0 mmol, 2.2 eq) is added dropwise (over 10 min). The resulting mixture is stirred at -78 C for lh and then DMF (2.0 g, 11.0 mmol, 1.1 eq) is added dropwise (over 10 min). The mixture is stirred at -78 C for an additional 30 min and then stirred at RT overnight. The reaction mixture is quenched with H20 (50 mL) and then concentrated in vacuo. The residue is triturated with saturated aqueous NH4C1 solution. The solid is collected by filtration, rinsed with ethyl acetate, and dried in vacuo to afford the product, 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde (E-3).

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, 22276-95-5, 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; INTELLIKINE, INC.; INFINITY PHARMACEUTICALS, INC.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; CASTRO, Alfredo, C.; EVANS, Catherine, A.; WO2011/146882; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 111196-81-7, 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 111196-81-7, name is 2-Chloro-5-ethylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Step-4: Synthesis of 5-ethyl-2-(5,6-dihydro-4-(4-(4-(methyl sulfonyl)phenyl)-1,2,5-thiadiazol-3-yl)pyridin-1(2H)-yl)pyrimidine To a stirred solution of 1,2,3,6-tetrahydro-4-(4-(4-(methylsulfonyl)phenyl)-1,2,5-thiadiazol-3-yl)pyridine hydrochloride (0.04 g, 0.111 mmol) and 2-chloro-5-ethylpyrimidine (0.023 g, 0.166 mmol) in DMF (5 mL) was added DIPEA (0.45 mL, 0.555 mmol) and stirred at 100 C. for 16 h. Reaction was monitored by TLC. On completion reaction mass was quenched with water, extracted with ethyl acetate. The organic layer was washed with water, brine, dried over sodium sulphate evaporated under reduced pressure obtained crude which was purified by silica gel (100-200 Mesh) column chromatography, eluent 25% EtOAc/Hexane to afford 5-ethyl-2-(5, 6-dihydro-4-(4-(4-(methylsulfonyl)phenyl)-1,2,5-thiadiazol-3-yl)pyridin-1(2H)-yl)pyrimidine (0.024 g, 51.06%) as off white solid. MS: 428.11 [M++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 111196-81-7, 2-Chloro-5-ethylpyrimidine.

Reference:
Patent; Mankind Pharma Ltd.; Patil, Rakesh Ishwar; Verma, Jeevan; Kumar, Puneet; Gunjal, Amol Pandurang; Rai, Himanshu; Rai, Santosh Kumar; Kumar, Anil; (106 pag.)US2017/291894; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 4994-86-9, 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. 4994-86-9, name is 4-Chloro-2-methylpyrimidine, molecular formula is C5H5ClN2, 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.

General procedure: Two solutions, one with the aryl halide (0.56 mmol, 1.0equivalent) in THF-H2O (2.5 mL, 3:2 v/v) and one with phenol (0.84mmol, 1.5 equivalent) and NaOH (0.84 mmol, 1.5 equivalent) in THF-H2O(2.5 mL, 3:2 v/v) were prepared and then introduced into Asia microfluidicreactor by Pump A & B.. The mixture was pumped through a preheated 1 mL glassmicrofluidic reactor at a predetermined flow rate to achieve the desiredresidence time. The crude product was collected in a flask and extracted withethyl acetate. The organic phase was combined, dried MgSO4 andconcentrated under reduced pressure. The isolated crude product was purifiedusing a prepacked silica cartridge on a Teledyne CombiFlash Rf 200instrument. Fractions corresponding to the product peak were combined andconcentrated using rotavap. For the synthesis of compound 3e and 3f correspondingsodium alkoxides were used as input for the second pump.

According to the analysis of related databases, 4994-86-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Alam, Mohammad Parvez; Jagodzinska, Barbara; Campagna, Jesus; Spilman, Patricia; John, Varghese; Tetrahedron Letters; vol. 57; 19; (2016); p. 2059 – 2062;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 959070-42-9, 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. 959070-42-9, name is Ethyl 4,6-dichloro-2-(methylthio)pyrimidine-5-carboxylate. A new synthetic method of this compound is introduced below.

To a solution of ethyl 4,6-dichloro-2-(methylthio)pyrimidine-5-carboxylate (47.0 g, 175.94 mmol) in DMF (470 mL) and diisopropylethylamine (100.43 mL, 582.7 mmol) was added ethyl 3-(phenylamino)propanoate (31.0 g, 160.4 mmol). The reaction mixture was heated to 100 C. and stirred for 7 h. Upon completion of the reaction (monitored by TLC), DMF was evaporated under reduced pressure and water (250 mL) was then added. The reaction mixture was extracted using EtOAc (200 mL×3). The combined organic layer was washed with water (500 mL×2), brine (500 mL), dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to give a residue. The residue was purified by silica gel column chromatography (using 0-20% Ethyl acetate in hexane) to afford ethyl 4-chloro-6-((3-ethoxy-3-oxopropyl)(phenyl)amino)-2-(methylthio)pyrimidine-5-carboxylate (55 g, 80.8% yield). 1H NMR (400 MHz, CDCl3): delta 7.38 (t, J=8.0 Hz, 2H), 7.31 (d, J=7.6 Hz, 1H), 7.18 (d, J=7/2 Hz, 2H), 4.26 (t, J=7.6 Hz, 2H), 4.05 (q, J=7.2 Hz, 2H), 3.47 (q, J=7.2 Hz, 2H), 2.68 (t, J=7.6 Hz, 2H), 2.54 (s, 3H), 1.19 (t, J=7.2 Hz, 3H), 1.08 (t, J=7.2 Hz, 3H). LCMS [M+H]; 424

At the same time, in my other blogs, there are other synthetic methods of this type of compound,959070-42-9, Ethyl 4,6-dichloro-2-(methylthio)pyrimidine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ArQule, Inc.; US2010/249110; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 3680-69-1, 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.3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H4ClN3, molecular weight is 153.5691, as common compound, the synthetic route is as follows.

N,N-Dimethylformamide (DMF) (47mL) was added to a mixture of 56 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (4.60g, 29.8mmol) and 57 N-iodosuccinimide (6.82g, 30.3mmol) under a nitrogen atmosphere. The solution was stirred at 22C for 2.5h before the mixture was poured into ice water (150mL). The precipitate was filtered, washed with water and n-pentane and dried to give 7.05g (25.2mmol, 85%) of 12 1 as a pale brown powder; mp. 187-188C (dec.) (lit [39]. 196-199C), Rf=0.16 (n-pentane/EtOAc, 10/1). 1H NMR (400MHz, DMSO-d6): 12.94 (br s, 1H), 8.59 (s, 1H), 7.94 (d, J=2.5, 1H). The spectroscopic data corresponded well with that reported previously [39].

The chemical industry reduces the impact on the environment during synthesis 3680-69-1, I believe this compound will play a more active role in future production and life.

Reference:
Article; Reiers°lmoen, Ann Christin; Han, Jin; Sundby, Eirik; Hoff, Bard Helge; European Journal of Medicinal Chemistry; vol. 155; (2018); p. 562 – 578;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 3934-20-1, 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.3934-20-1, name is 2,4-Dichloropyrimidine, molecular formula is C4H2Cl2N2, molecular weight is 148.9781, as common compound, the synthetic route is as follows.

A stirred solution of 2,4-dichloropyrimidine (5.00g, 36.5mmol) and diisopropylethylamine (14.0ml, 80.4mmol) in EtOH (60ml) at 0C was treated with morpholine (3.18ml, 36.5mmol) and allowed to warm to ambient temperature overnight. The solution was poured into brine and extracted with DCM. The organics were dried (MgS04), filtered and evaporated. The residue was purified by column chromatography (Si02, 5% EtOH in DCM) to afford the title compound IIIc as a white solid (1.3g, 36%). XH NMR (300 MHz, DMSO-d6) delta 8.10 (d, J = 6.2 Hz, 1H), 6.83 (d, J = 6.2 Hz, 1H), 3.72 – 3.49 (m, 8H).

The chemical industry reduces the impact on the environment during synthesis 3934-20-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; AB SCIENCE; BENJAHAD, Abdellah; MARTIN, Jason; SCHALON, Claire; PEZ, Didier; CHEVENIER, Emmanuel; SANDRINELLI, Franck; PICOUL, Willy; MOUSSY, Alain; WO2015/144614; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 5018-38-2, Adding some certain compound to certain chemical reactions, such as: 5018-38-2, name is 4,6-Dichloro-5-methoxypyrimidine,molecular formula is C5H4Cl2N2O, 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 5018-38-2.

To a solution of 4,6-dichloro-5-methoxypyrimidine (20.00 g, 1 12 mmol) in DCE (250 mL) at 0 C was added aluminum trichloride (22.35 g, 168 mmol) in two portions. The reaction mixture was stirred at 0 C for 10 min, then at 50 C for 4 hr. The mixture was cooled to 0 C and aqueous HCI (1 M, 120 mL) followed by MeOH (50 mL) were added slowly while stirring vigorously. The mixture was poured into water and extracted with Et20 (3x). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated. The residue was dried in vacuum to afford INT 15 as a beige solid. UPLC-MS: MS (ESI): [M-H]” 163.0, rt = 0.44 min. 1 H NMR (DMSO-d6): delta (ppm) 1 1 .69 (s, br, 1 H), 8.38 (s, 1 H).

According to the analysis of related databases, 5018-38-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; BRIARD, Emmanuelle; AUBERSON, Yves; CENNI, Bruno; PULZ, Robert Alexander; ANGST, Daniela; (62 pag.)WO2016/79669; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 7226-23-5, Adding some certain compound to certain chemical reactions, such as: 7226-23-5, name is 1,3-Dimethyltetrahydropyrimidin-2(1H)-one,molecular formula is C6H12N2O, 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 7226-23-5.

A solution of diisopropylamine (29.2 mL, 0.21 mol) in dry tetrahydrofuran (186 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (62 mL) was cooled to -78 C. and then treated with a 2.5M solution of n-butyllithium in hexanes (83.4 mL, 0.21 mol). The yellow-orange reaction mixture was stirred at -78 C. for 35 min and then slowly treated with a solution of 4-(methanesulfonyl)phenyl acetic acid methyl ester (45.35 g, 0.20 mol) in dry tetrahydrofuran (186 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (62 mL). The reaction mixture turned dark in color. The reaction mixture was then stirred at -78 C. for 50 min, at which time, a solution of iodomethylcyclopentane (50.08 g, 0.24 mol) in a small amount of dry tetrahydrofuran was added slowly. The reaction mixture was then stirred at -78 C. for 50 min, and then allowed to warm to 25 C., where it was stirred for 36 h. The reaction mixture was quenched with water (100 mL), and the resulting reaction mixture was concentrated in vacuo to remove tetrahydrofuran. The remaining residue was diluted with ethyl acetate (1.5 L). The organic phase was washed with a saturated aqueous sodium chloride solution (1*500 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 3/1 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-methanesulfonylphenyl)propionic acid methyl ester (41.79 g, 68%) as a yellow viscous oil: EI-HRMS m/e calcd for C16H22O4S (M+) 310.1239, found 310.1230.

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. 7226-23-5, 1,3-Dimethyltetrahydropyrimidin-2(1H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bizzarro, Fred Thomas; Corbett, Wendy Lea; Grippo, Joseph Francis; Haynes, Nancy-Ellen; Holland, George William; Kester, Robert Francis; Sarabu, Ramakanth; US2001/39344; (2001); 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. 14080-59-2, name is 4-Chlorothieno[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

Under argon atmosphere, 2,4-difluorophenylboronic acid (5.9 g, 35 mmol) was added to a 250 mL round bottom flask.4-chlorothiophene [2,3-d]pyrimidine (5.1 g, 30 mmol),Pd(dppf)Cl2 (440 mg, 0.6 mmol), K2CO3 (5.5 g, 40 mmol),60mL 1,4-dioxane and 20mL water,The mixture was heated at 90 C with stirring for 6 h.Cool to room temperature, quench with water, extract with dichloromethane, and remove the solvent on a rotary evaporator.Purification by column chromatography. A white solid (6.1 g, 82%) was obtained.

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, 14080-59-2, 4-Chlorothieno[2,3-d]pyrimidine.

Reference:
Patent; Wuhan University; Yang Chuluo; Jiang Bei; Ning Xiaowen; (32 pag.)CN107573386; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 89284-85-5, 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. 89284-85-5, name is Methyl 2,5,6-trichloropyrimidine-4-carboxylate, molecular formula is C6H3Cl3N2O2, 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.

To a solution of 1-((R)-2-amino-propoxy)-3-chloro-propan-2-ol hydrochlorideand 3-((R)-2-amino-propoxy)-2-chloro-propan-1 -ol hydrochloride (10,65 g;52,157 mmol; 100,00 mol%) in 2-propanol (1 56,48 ml; 2046,654 mmol;3924,00 mol%) was added N-ethyldiisopropylamine (26,61 ml; 156,472 mmol;300,00 mol%) and stirred for 5 minutes. 2,5,6-Trichloro-pyrimidine-4-carboxylicacid methyl ester (12,59 g; 52,157 mmol; 100,00 mol%) was added and the reaction mixture was stirred at RT for 14 h. To the reaction mixture was addeddichloromethane and 1 N HCI. The aqueous layer was extracted withdichloromethane. The combined organic layers were dried over sodium sulfate, the solvent removed under vacuo and the residue purified by coloumn chromatography (petroleum benzene I ethyl acetate) to afford the product as as yellow oil (1 0.8g, 52 %); LCMS (method C): 1 .52 mm (purity 94.1%); [MH+] 372.00 mlz.

According to the analysis of related databases, 89284-85-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK PATENT GMBH; BURGDORF, Lars; DORSCH, Dieter; TSAKLAKIDIS, Christos; (189 pag.)WO2017/202748; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia