Tag: M.W:200-300

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

To a solution of 5-bromo-4-chloro-7H-pyrrolo[2,3-i Jpyrimidine (40.0 g, 173 mmol) in dry tetrahydrofuran (700 mL) at -78 C was added rc-butyl lithium (195 mL, 2.5 M solution in hexane, 487 mmol) over the period of 2 hours. The reaction mixture was stirred for another 30 minutes at -78 C, after which ethyl chloroformate (17.8 mL, 186mmol) was added over 30 minutes. The reaction mixture was stirred for 2 hours at -60 C and then the temperature was slowly increased to 30 C. The reaction mixture was allowed to stir for 12 hours at 30 C. The progress of the reaction was monitored by TLC using 25% ethyl acetate in petroleum ether using iodine and 254 nm UV light to visualize the spot. The reaction mixture was then quenched with saturated solution of ammonium chloride (200 mL) at 0 C and the reaction mixture was extracted with ethyl acetate (*3). The combined organic layers were washed with water, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford a crude reaction mixture. The residue was purified by chromatography on silica eluting with 5-100% ethyl acetate/petroleum ether to afford ethyl 4-chloro-7H-pyrrolo[2,3-i ]pyrimidine-5- carboxylate as pale yellow solid. LRMS (ESI) calc’d for C9H7C1N302 [M-H]+: 224; found 224. 1H NMR (400 MHz, DMSO-D6): delta 13.28 (s, 1H), 8.70 (s, 1H), 8.39 (s, 1H), 4.31 (q, J= 7.2, 6.8 Hz, 2H), 1.34 (t, J= 7.6, 6.8 Hz, 3H)

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; MERCK SHARP & DOHME CORP.; AHEARN, Sean, P.; CHRISTOPHER, Matthew; JUNG, Joon; PU, Qinglin; RIVKIN, Alexey; SCOTT, Mark, E.; WITTER, David, J.; WOO, Hyun Chong; CASH, Brandon; DINSMORE, Christopher; GUERIN, David; WO2013/85802; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 914612-23-0, 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. 914612-23-0, name is 6-Benzyl-4-chloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine, molecular formula is C14H14ClN3, 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 ETo a solution of 6-benzyl-4-chloro-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidine (3.9 g, 15.0 mmol) in EtOH (50 mL) was added compound 5 (2.3 g, 15.0 mmol) and DIEA (3.87 g, 30 mmol). The mixture was stirred at 80 C for 3 hours then the mixture was evaporated to dryness. The crude product was purified by silica gel chromatography eluted with PE: EA = (5: 1) to give the desired product (4.08 g)

According to the analysis of related databases, 914612-23-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; COBURN, Craig; WANG, Jiabing; SANTARELLI, Vince; HU, Shuangxi; CUI, Mingxiang; HU, Bin; DONG, Jingchao; LUO, Yunfu; SOLL, Richard, M; WO2011/103715; (2011); 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. 51940-64-8, name is Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate

(R)-tetrahydro-2H-pyran-3-amine hydrochloride (1.00 g, 7.27 mmol) in acetonitrile (5 ml) was added dropwise to a mixture of DIPEA (3.16 ml, 18.2 mmol) and ethyl 2,4- dichloropyrimidine-5-carboxylate (1.61 g, 7.27 mmol) in acetonitrile (30 ml) at 0C over a period of 5 minutes under air. The resulting suspension was stirred for 4 h, slowly allowing to warm to rt and stirred at rt overnight. The reaction mixture was evaporated to dryness to remove MeCN, diluted with EtOAc (100 mL), and washed with water then sat. brine. The organic layer was dried over MgS04, filtered and evaporated. The resulting crude product was purified by fee, elution gradient 0 to 50% EtOAc in heptane, to afford the title compound (0.936 g, 45%) as a yellow oil; 1H NMR (400 MHz, DMSO) 1.33 (3H, t), 1.57 (1H, dt), 1.71 (2H, dtd), 1.91 (1H, ddt), 3.48 (1H, dd), 3.55 – 3.66 (2H, m), 3.75 (1H, dd), 4.11 – 4.2 (1H, m), 4.33 (2H, q), 8.58 (1H, d), 8.65 (1H, s); m/z MH+286.

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, 51940-64-8, Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate.

Reference:
Patent; ASTRAZENECA AB; CANCER RESEARCH TECHNOLOGY LIMITED; FINLAY, Maurice, Raymond, Verschoyle; GOLDBERG, Frederick, Woolf; TING, Attilla, Kuan, Tsuei; (103 pag.)WO2018/114999; (2018); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 10244-24-3, Adding some certain compound to certain chemical reactions, such as: 10244-24-3, name is 4,4′-(6-Chloropyrimidine-2,4-diyl)dimorpholine,molecular formula is C12H17ClN4O2, 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 10244-24-3.

A solution of 40 g of 2,4-[bis-morpholino]-6-chloropyrimidine and 34 g of piperazine in 60 g of pyridine is heated at 100 for 24 h. The mixture is partitioned between methylene chloride and aqueous potassium carbonate. The organic phase is filtered through sodium sulfate and concentrated. The residue is chromatographed (methylene chloride to 4% methanol/1% ammonium hydroxide/methylene chloride) to give the title compound, NMR (CDCl3) 2.90, 3.50, 3.75, 3.80 and 5.10 delta.

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. 10244-24-3, 4,4′-(6-Chloropyrimidine-2,4-diyl)dimorpholine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Upjohn; US5120843; (1992); A;,
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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. 31462-54-1, name is 2-Iodopyrimidine. A new synthetic method of this compound is introduced below., name: 2-Iodopyrimidine

Add in the reaction tube2-iodopyrimidine (0.5 mmol, 1.0 eq.)And sodium dithionite (0.55mmol, 1.1 equivalent),Replace the air in the test tube with high purity nitrogen.Add 3 mL of N,N-dimethylformamide as solvent.The reaction was stirred for 16 hours (purity of 98%) by heating to 90 C.After the reaction was cooled, tetrabutylammonium iodide (0.05 mmol, 0.1 equivalent) and potassium iodide (0.6 mmol, 1.2 equivalent) were added to the reaction mixture.And 4-methylbenzyl bromide (1.0 mmol, 2.0 eq.),Replace the air in the test tube with high purity nitrogen.Stir at room temperature for 10 hours.The reaction was quenched with saturated brine.Extracted with ethyl acetate,Combine the organic phase,dry,Concentrate and separate by column chromatography.The target product Ib was obtained in 76% yield.

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, 31462-54-1, 2-Iodopyrimidine.

Reference:
Patent; Jiaxing College; Qiu Guanyinsheng; Li Yuewen; Wu Jie; (13 pag.)CN109180572; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1780-40-1, 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.1780-40-1, name is 2,4,5,6-Tetrachloropyrimidine, molecular formula is C4Cl4N2, molecular weight is 217.8682, as common compound, the synthetic route is as follows.

To a solution of 2,4,5, 6-tetrachloropyrimidine (1 kg, 4.63 mol) in THF (6 L) was added IN NaOH (6 L, 6.0 mol) drop wise, and the mixture was stirred overnight at room temperature. The solution was acidified with IN HC1 and extracted with DCM (3x). The combined organics were dried (Na2S04) and concentrated in vacuo. The solids were slurried in Et20 for 30 min, filtered, washed with Et20 and dried to give 635 g (69%) of the title compound. LCMS (C18 column, column size: 4.6*50 mm; mobile phase: 20%-40%, Acetonitrile-Water-0.02% NH4OAc): Rt= 2.785 min; [M+H] Calc’d for C4HC13N20, 199; Found, 199.

Statistics shows that 1780-40-1 is playing an increasingly important role. we look forward to future research findings about 2,4,5,6-Tetrachloropyrimidine.

Reference:
Patent; CELGENE QUANTICEL RESEARCH, INC.; CHEN, Young K.; KANOUNI, Toufike; KALDOR, Stephen W.; STAFFORD, Jeffrey Alan; VEAL, James Marvin; TAVARES-GRECO, Paula Alessandra; KREILEIN, Matthew Michael; (41 pag.)WO2017/79670; (2017); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 941685-26-3, 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-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, 941685-26-3, blongs to pyrimidines compound. Recommanded Product: 941685-26-3

A solution of 4-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3- fif]pyrimidine (15.0 g, 52.9 mmol) in N,N-dimethylformamide (200 mL) was added to Pd(dppf)Cl2 (2.2 g, 2.7 mmol), (3-nitrophenyl)boronic acid (13.3 g, 79.7 mmol) under nitrogen. A solution of sodium carbonate (6.00 g, 56.6 mmol) in water (60.0 mL) was then added and the reaction was stirred for 3 hours at 100 C. The resulting mixture was concentrated in vacuo, and the solids were filtered and extracted with dichloromethane (*3). The combined organic layers were washed with H20, brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The reaction was then purified by chromatography using silica gel, eluting with 0-33% EtOAc/petroleum ether. The product was collected and concentrated in vacuo to afford 4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-£ lpyrirnidine as a yellow solid. LRMS (ESI) calc’d for [M+H]+: 371, found 371.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,941685-26-3, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; AHEARN, Sean, P.; CHRISTOPHER, Matthew; JUNG, Joon; PU, Qinglin; RIVKIN, Alexey; SCOTT, Mark, E.; WITTER, David, J.; WOO, Hyun Chong; CASH, Brandon; DINSMORE, Christopher; GUERIN, David; WO2013/85802; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 10397-13-4, 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 10397-13-4 as follows.

To a rubber-septum-capped vial containing 4, 6-dichloro-2-morpholinopyrimidine (0. 2 M in dioxane, 0. 25 mL) and L-PYRIDIN-2-YL-PIPERAZINE (0. 2 M in dioxane, 0. 28 mL) add aqueous K3P04 (0. 5 M, 0. 125 mL). Heat the mixture at 90C for 24 hours. Cool the mixture and concentrate under reduced pressure. Partition between ethyl acetate and water, dry (NA2S04) the organic layer and concentrate under reduced pressure. Filter the crude product through a pad of silica gel (1 : 1 ethyl acetate/hexanes) and remove the solvent under reduced pressure to give the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10397-13-4, its application will become more common.

Reference:
Patent; NEUROGEN CORPORATION; WO2005/7646; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 4359-87-9, name is 2,4,6-Trichloro-5-nitropyrimidine, the common compound, a new synthetic route is introduced below. COA of Formula: C4Cl3N3O2

To a stirred suspension of K-1 (1.00 g, 4.38 mmol) and DIEA (1.83 mL, 10.51 mmol) in DCM (15 mL) at 0 C is slowly added K-2 (1.00 g, 9.30 mmol) and the reaction is allowed to slowly warm to 25 C and stirred for 4h. The volatiles are removed under reduced pressure and the resulting residue is purified by Si02 flash chromatography to yield K-3.

The synthetic route of 4359-87-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BRUNETTE, Steven Richard; CSENGERY, Johanna; HUGHES, Robert Owen; LI, Xiang; SIBLEY, Robert; TURNER, Michael Robert; XIONG, Zhaoming; (88 pag.)WO2017/58831; (2017); 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.56844-12-3, name is 6-Bromo-4-chlorothieno[2,3-d]pyrimidine, molecular formula is C6H2BrClN2S, molecular weight is 249.52, as common compound, the synthetic route is as follows.category: pyrimidines

General procedure: Compound 1 (1.00 g, 4.01 mmol) was mixed with the benzylamine (2-3 eq.) and i-PrOH (2-10 mL) and agitated at 80 C for 1-50 h, under nitrogen atmosphere. Then the mixture was cooled to rt, concentrated in vacuo, diluted with water (50 mL) and diethyl ether (100 mL) or EtOAc (100 mL). After phase separation, the water phase was extracted with more diethyl ether (2×50 mL) or EtOAc (2×50 mL). The combined organic phases were washed with saturated aq NaCl solution (25-50 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude oil was purified by drying under reduced pressure to constant weight, by silica-gel column chromatography or crystallized as specified for each individual compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,56844-12-3, 6-Bromo-4-chlorothieno[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Bugge, Steffen; Moen, Ingri Ullestad; Kragseth Sylte, Kent-Ove; Sundby, Eirik; Hoff, Bard Helge; European Journal of Medicinal Chemistry; vol. 94; (2015); p. 175 – 194;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia