Month: February 2021

Electric Literature of 32779-37-6, 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.32779-37-6, name is 2,5-Dibromopyrimidine, molecular formula is C4H2Br2N2, molecular weight is 237.88, as common compound, the synthetic route is as follows.

5.4 A mixture of 1.06 g (5.85 mmol) trans-4-(4-Methylamino-cyclohexyl)-but-3-yn-1-ol, 1.67 g (7.02 mmol) of 2,5-dibromo-pyrimidine [Brown, Desmond J.; Arantz, B. W., Pyrimidine reactions. XXII. Relative reactivities of corresponding chloro-, bromo-, and iodopyrimidines in aminolysis. J. Chem. Soc. C (1971), Issue 10, 1889-91] and 3.38 ml (19.88 mmol) N-ethyldiisopropylamine were heated for 2 h at 85 C., diluted with 1 ml DMA and heated for 3.5 h at 85 C. The reaction was cooled, evaporated and partitioned between aqueous saturated NaHCO3/Et2O (3*). The organic phases were washed with aqueous 10% NaCl, dried (NaSO4) and evaporated. Flash chromatography on silica gel (hexane/EtOAc 9:1 to 1:1) gave 1.37 g (69%) of trans-4-{4-[(5-Bromo-pyrimidin-2-yl)-methyl-amino]-cyclohexyl}-but-3-yn-1-ol, MS: 338 (MH+, 1Br).

Statistics shows that 32779-37-6 is playing an increasingly important role. we look forward to future research findings about 2,5-Dibromopyrimidine.

Reference:
Patent; Ackermann, Jean; Aebi, Johannes; Dehmlow, Henrietta; Maerki, Hans-Peter; Morand, Olivier; US2003/186984; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1195768-23-0, N-(3-(2-(tert-Butyl)-5-(2-chloropyrimidin-4-yl)thiazol-4-yl)-2-fluorophenyl)-2,6-difluorobenzenesulfonamide, 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, 1195768-23-0, blongs to pyrimidines compound. SDS of cas: 1195768-23-0

A suspension of N-(3-(2-(tert-butyl)-5-(2-chloropyrimidin-4-yl)thiazol-4-yl)-2- fluorophenyl)-2,6-difluorobenzenesulfonamide (50.0mg, 0.092mmol) and aniline (9.0mg, 0.097mmol) in iPrOH (lmL), in presence of catalytic concentrated HC1, was stirred at 100C for lh, then at 80C overnight. The mixture was concentrated under reduced pressure. The residue was partitioned between EtOAc and saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried over sodium sulphate, filtered and the filtrate was concentrated under vacuum. Purification by flash chromatography on silica gel (cHex-EtOAc, 1/0 to 0/1) afforded the title compound 1 (40mg, 72%). lU NMR (CDC13): 8.09 (d, 1H, J = 5.2 Hz); 7.84 (bs, 1H); 7.72 (m, 1H); 7.48 (d, 2H, J = 7.7Hz); 7.44-7.36 (m, 3H); 7.29 (t, 2H, J = 7.5Hz); 7.24 (t, 1H, J = 7.3Hz); 7.02 (t, 1H, J = 7.7Hz); 6.92 (t, 2H, J = 8.7Hz); 6.28 (d, 1H, J = 5.2Hz); 1.48 (s, 9H). LC/MS (ES+): 596.2 (M+l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1195768-23-0, its application will become more common.

Reference:
Patent; CELLIPSE; PRUDENT, Renaud; PAUBLANT, Fabrice; (74 pag.)WO2018/55097; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 583878-42-6, Adding some certain compound to certain chemical reactions, such as: 583878-42-6, name is Ethyl 4-chloro-6-methyl-2-(methylthio)pyrimidine-5-carboxylate,molecular formula is C9H11ClN2O2S, 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 583878-42-6.

To a solution of Intermediate III-A1 (400 mg, 1 mmol) dissolved in MeOH (4 mL) was added conc. HCl (4 mL) . The resulting mixture was concentrated at 50 to dryness. The residue was dissolved in n-BuOH (20 mL) , and then added DIEA (1 mL) and ethyl 4-chloro-6-methyl-2- (methylthio) pyrimidine-5-carboxylate (246 mg, 1 mmol) . The mixture was stirred at rt. for 2h, and then concentrated to remove the solvent. The residue was purified by flash column chromatography to afford the title compound as a solid (500 mg) . Yield: 97.8. MS (ESI) : calcd. value for C24H23ClN6O3S is 510.12, m/z measured value is 511.1 (M+1)+.

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. 583878-42-6, Ethyl 4-chloro-6-methyl-2-(methylthio)pyrimidine-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-Guo; DAI, Guangxiu; JIA, Hong; ZHANG, Zhulin; WENG, Jianyang; VENABLE, Jennifer Diane; BEMBENEK, Scott Damian; CHAI, Wenying; MEDUNA, Steven Paul; KEITH, John Matthew; ECCLES, Wendy; LEBSACK, Alec Donald; JONES, William Moore; SMITH, Russell Christopher; (195 pag.)WO2016/119707; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 14080-59-2 ,Some common heterocyclic compound, 14080-59-2, molecular formula is C6H3ClN2S, 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.

Examples 308 and 309 Synthesis of 6-bromo-4-chlorothieno[2,3-d]pyrimidine and 6-bromo-2-butyl-4-chlorothieno[2,3-d]pyrimidine n-BuLi (1.6 M in hexane, 1.9 ml, 2.5 mmol) in THF (8 ml) was cooled to -78 C. 4-Chlorothieno[2,3-d]pyrimidine (0.34 g, 2.0 mmol) was dissolved in THF (2 ml) and slowly added to the reaction mixture over 5 minutes. After 20 min, CBr4 (0.73 g, 2.2 mmol) in THF (3 ml) was slowly added to the reaction mixture. The temperature was maintained at -78 C. for 20 minutes and then warmed to room temperature for 2 hours. The mixture was poured into water and extracted with chloroform, dried over sodium sulfate, and concentrated in vacuo. The crude residue was purified by silica gel chromatography (EtOAc/hexane 40:1) to yield two pure compounds a white solid (example 203: 0.13 g, 25% and example 204: 0.16 g, 26%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14080-59-2, its application will become more common.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN, K.U.LEUVEN R&D; De Jonghe, Steven; Gao, Ling-Jie; Herdewijn, Piet; Herman, Jean; Jang, Miyeon; Leyssen, Pieter; Louat, Thierry; Neyts, Johan; Pannecouque, Christophe; Vanderhoydonck, Bart; US2013/190297; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 211244-81-4, 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. 211244-81-4, name is 2-(Methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one, molecular formula is C8H7N3OS, 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.

EXAMPLE 52-MethanesuIfinyl-8H-pyrido[2,3-d]pyrimidin-7-one; To a suspension of 2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (WO 9833798 A2, 5.0 g, 25.9 mmol) in CH2Cl2 (100 mL), CHCl3 (50 mL) and MeOH (10 mL, the starting material still did not dissolve) was added the oxaziridine (8.11 g, 31.05 mmol, 1.2 equiv) as a solid. The reaction became homogenous after 3 h and was stirred overnight at RT. The reaction was concentrated and CH2Cl2ZMeOH was added to dissolve the residue. Much of the solid did not dissolve so the mixture was filtered to give 2-Methanesulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one, as an off-white solid (2.31 g, 11.04 mmol, 43%). MS: APCI: M+l: 210.1 (Exact Mass: 209.03).

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 211244-81-4, 2-(Methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2006/90272; (2006); 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. 271-70-5, name is 7H-Pyrrolo[2,3-d]pyrimidine, the common compound, a new synthetic route is introduced below. Product Details of 271-70-5

A mixture of ethyl 2-(6-bromo-2-(4-methoxybenzyl)-3-oxoisoindolin-1-yl)acetate (3, 439 mg, 1.05 mmol), 7H-pyrrolo[2,3-d]pyrimidine (4, 125 mg, 1.05 mmol), tris(dibenzylideneacetone)dipalladium(0) (97 mg, 0.10 mmol), XantPhos (61 mg, 0.10 mmol), and cesium carbonate (752 mg, 2.31 mmol) in 1,4-dioxane (25 mL) was purged with argon for 5 min. The reaction was stirred at 110 C. for 16 h. Upon cooling, the reaction mixture was diluted with ethyl acetate, washed with half saturated aqueous sodium bicarbonate solution, and then with brine. The organic layer was dried over magnesium sulfate, filtered and concentrated. The crude product was purified via column chromatography (silica, methanol/dichloromethane gradient from 0-5% to afford ethyl 2-(2-(4-methoxybenzyl)-3-oxo-6-(7H-pyrrolo[2,3-d]pyrimidin-7-yl)isoindolin-1-yl)acetate (5). Yield: 333 mg, 70%; MS (ESI) m/z 457.4[M+1]+.

The synthetic route of 271-70-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EFFECTOR THERAPEUTICS, INC.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; (55 pag.)US2017/121339; (2017); 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. 63558-65-6, name is 4-Chloro-5-iodopyrimidine, the common compound, a new synthetic route is introduced below. Recommanded Product: 4-Chloro-5-iodopyrimidine

Step 3: N-4′-[(5-Iodopyrimidin-4-yl)amino]-6-methylbiphenyl-3-yl-3-(trifluoromethyl)benzamideTo lambda^-(4′-amino-6-methylbiphenyl-3-yl)-3-(trifluoromethyl)benzamide (60.0 mg, 0.162 mmol) was added 4-chloro-5-iodopyrimidine (39 mg, 0.16 mmol) followed by ethanol (0.47 mL). The reaction was heated to 80 0C in a sealed tube until LCMS indicated complete reaction, typically 1 -2 hours. The reaction was cooled to ambient temperature and the solvent was evaporated. The residue was partitioned between saturated aqueous NaHCO3 and EtOAc, the organic phase was washed with brine, dried (MgSO4) and evaporated to leave the crude product, which was then purified by column chromatography to give the final compound (39.9 mg, 42.88%). 1H NMR (400 MHz, CDCl3): delta 8.61 (s, 2H), 8.14 (s, IH), 8.08 (d, IH), 7.95 (s, IH), 7.81 (d, IH), 7.5-7.7 (m, 5H), 7.40 (m, 3H), 7.29 (d, IH), 2.29 (s, 3H). MS (EI) m/z = 575 (M+H).

The synthetic route of 63558-65-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INCYTE CORPORATION; WO2008/79965; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 4983-28-2, 2-Chloro-5-hydroxypyrimidine, 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, 4983-28-2, blongs to pyrimidines compound. Recommanded Product: 4983-28-2

To a solution of 2-((6-(tert-butylsulfonyl)-4-((4,5-dimethyl-lH-pyrazol-3-yl)amino)quinazolin-7- yl)oxy)ethanol (247 mg, 0.589 mmol) in THF (5 mL) was added 2-chloropyrimidin-5-ol (85 mg, 0.648 mmol), triphenylphosphine (232 mg, 0.883 mmol) and DIAD (0.172 mL, 0.883 mmol) and the reaction was stirred at 20 ¡ãC under an atmosphere of nitrogen for 42 hours. The reaction was concentrated, and the residue was subjected directly to purification by flash chromatography (60g pre-packed C-18 SNAP cartridge: 5percent to 30percent acetonitrile (0.1percent formic acid) in water (0.1percent formic acid)). The desired fractions were combined and concentrated to afford the title compound (167 mg, 0.31 mmol, 53.3 percent yield). LCMS RT= 0.73 min, ES+ve 532.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4983-28-2, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CASILLAS, Linda N.; HARLING, John David; MIAH, Afjal Hussain; SMITH, Ian Edward David; RACKHAM, Mark David; (204 pag.)WO2017/182418; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 90914-41-3, 3-Bromo-4-chloro-1H-pyrazolo[3,4-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, Quality Control of 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine, blongs to pyrimidines compound. Quality Control of 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine

1-(1-benzyl-4-piperidinyl)-3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine (Intermediate C) 3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine (Intermediate B) (5.0 g, 21.42 mmol), 1-benzyl-4-piperidinol (8.2 g, 42.83 mmol) and triphenylphosphine (11.23 g, 42.83 mmol)were suspended in 250 ml of tetrahydrofuran. The reaction mixture was cooled in an ice-water bath and diethyl azodicarboxylate (6.8 ml, 42.83 mmol) was added dropwise. 10 minutes later, the reaction mixture was allowed to warm up to room temperature. After stirring for 2 hours, solvent was removed and the residue was taking into ethyl acetate. The organic layer was washed, dried and evaporated. The crude product was passed through Biotage flash column using dichloromethane/ethyl acetate (90:10) as the mobile phase to yield 10.56 g of 1-(1-benzyl-4-piperidinyl)-3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine. The product was 61% pure with a HPLC retention time of 12.46 min. (HPLC condition: 5 to 95% CH3CN in 0.1 N aqueous ammonium acetate over 20 min., the column size is 3.9*150 mm, 300 A).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,90914-41-3, 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Abbott Laboratories; US2002/156081; (2002); 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. 33034-67-2, name is 2-Chloro-4-(trifluoromethyl)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 2-Chloro-4-(trifluoromethyl)pyrimidine

General procedure: To a solution of D47 (4.86 mmol) in DMF (8 mL), K2CO3 (8.68 mmol) and Ar1-X (where X is2-chloro or fluoro; 5.8 mmol) were added. The reaction mixture was heated at 80-130 ¡ãC until complete conversion of the starting material. The resulting mixture was poured into aqueous solution of NH4Cl and extracted with AcOEt. The organic layer was dried andconcentrated to obtain a crude mixture which was purified by silica gel chromatography (cyclohexane/ethyl acetate from 10/0 to 8/2) to give the title compound as single diasteroisomer.

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, 33034-67-2, 2-Chloro-4-(trifluoromethyl)pyrimidine.

Reference:
Patent; ROTTAPHARM SPA; STASI, Luigi Piero; ROVATI, Lucio; WO2013/139730; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia