Category: 16019-33-3

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. 16019-33-3, name is 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde, the common compound, a new synthetic route is introduced below. Safety of 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde

4,6-Dichloropyrimidine-5-acetaldehyde 1 (2.0 g, 10.5 mmol) dissolved in 80 mLEthanol, adding triethylamine (3.0 mL,21.06 mmol), stirred at room temperature for 10 min.Then tert-butylamine (2.2 mL, 21.06 mmol) was added to the mixture, and the reaction solution wasAfter stirring at 90 C for 6 h, the reaction was monitored by TLC. After the reaction is completed, after evaporating the solvent,The crude reaction product was dissolved in dichloromethane/water.(volume ratio = 1:1) 100 ml × 3 times.Separation and purification by column chromatography to obtain a white solid1.0 g (yield 55.2%).

The synthetic route of 16019-33-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan University Huaxi Hospital; He Yang; Chai Yingying; Li Weimin; Zhou Xinglong; (20 pag.)CN108794483; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 16019-33-3, 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. 16019-33-3, name is 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde. A new synthetic method of this compound is introduced below.

A mixture of (4,6-dichloro-pyrimidin-5-yl)-acetadehyde (555 mg, 2.91 mmol), N-(trans-4- aminocyclohexyl)-carbamic acid 1 ,1-dimethylethyl ester (623 mg, 2.91 mmol) and DIEA (508 mu, 2.91 mmol) in EtOH (5 mL) was stirred for 18 h at reflux, allowed to cool at rt, concentrated and diluted with DCM/H20. The aqueous layer was extracted with DCM. The combined organic extracts were dried (Na2S0 ), filtered and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate, 70:30) to afford to afford 348 mg of the title compound as a white soild: ES-MS: 351.1 [M+H]+; tR= 4.86 min (Method C), Rf = 0.29 (hexane/ethyl acetate, 70:30).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16019-33-3, 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; IRM LLC; CHEN, Bei; FAIRHURST, Robin, Alec; FLOERSHEIMER, Andreas; FURET, Pascal; GUAGNANO, Vito; JIANG, Songchun; LU, Wenshuo; MARSILJE, Thomas, H.; MCCARTHY, Clive; MICHELLYS, Pierre-Yves; STAUFFER, Frederic; STUTZ, Stefan; VAUPEL, Andrea; WO2011/29915; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 16019-33-3 , The common heterocyclic compound, 16019-33-3, name is 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde, molecular formula is C6H4Cl2N2O, 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.

(1R,2S,3R,5R)-3-Amino-5-(hydroxymethyl)cyclopentane-1,2-diol hydrochloride (40 g, 218 mmol) was dissolved at room temperature in methanol (400 mL) and 2,2-dimethoxypropane (54 mL, 436 mmol), and methanesulfonic acid(14 mL, 218 mmol) was added thereto dropwise in an ice bath with stirring so as to keep the internal temperature at 7C or lower. After the mixture was stirred in an ice bath for 5 minutes and at room temperature overnight, triethylamine (122 mL, 872 mmol) was added thereto dropwise in an ice bath so as to keep the internal temperature at 10C or lower. After the mixture was stirred in an ice bath for 5 minutes and at room temperature for 30 minutes, the solvent was distilled off under reduced pressure, thereby obtaining the title compound as a crude isomeric mixture (102 g). LCMS (ESI) m/z 188 [M+H]+ The crude isomeric mixture (102 g) of ((3aR,4R,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methanol and (4aR,6R,7S,7aR)-6-amino-2,2-dimethylhexahydrocyclopenta[d][1,3]dioxin-7-ol obtained in step 1 of Reference Example 93, and 2-(4,6-dichloropyrimidin-5-yl)acetaldehyde (46 g, 240 mmol) was suspended in 2-butanol (400 mL). Then, triethylamine (61 mL, 436 mmol) was added thereto at room temperature, and the reaction solution was stirred at 80C overnight. After the reaction solvent was distilled off under reduced pressure, the residue was partitioned with the addition of ethyl acetate and an aqueous sodium hydrogen carbonate solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline, and dried over sodium sulfate, followed by distilling off the solvent, thereby obtaining the title compound as a crude isomeric mixture (72 g). LCMS (ESI) m/z 324 [M+H]+

The synthetic route of 16019-33-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Taiho Pharmaceutical Co., Ltd.; ISHIDA, Keiji; (139 pag.)EP3395345; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 16019-33-3, 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde, 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, Product Details of 16019-33-3, blongs to pyrimidines compound. Product Details of 16019-33-3

1 g of 2-(4,6-dichloropyrimidin-5-yl)acetaldehyde was dissolved in 20 mL of THF, and the reactor was cooled to -78 C. 4.36 mL of a methylmagnesium bromide diethyl ether solution (3 mol/L) was slowly added dropwise dropwisely thereto. At the same temperature, the mixture was stirred for 1 hour, and a saturated aqueous ammonium chloride solution was slowly added thereto to terminate the reaction. The reaction mixture was stirred at room temperature for 10 minutes and placed in a separatory funnel, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and then dried over sodium sulfate to remove the solvent. The residue was purified by basic silica gel chromatography (hexane/ethyl acetate=1/0->3/1), thereby obtaining 446 mg of the title compound. (1322) Physical Properties: m/z [M+H]+ 207.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16019-33-3, 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; TAIHO PHARMACEUTICAL CO., LTD.; MIYAZAKI, Isao; SHIMAMURA, Tadashi; KATO, Masanori; FUJITA, Hidenori; IGUCHI, Satoru; (161 pag.)US2018/9818; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 16019-33-3, 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde, 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, name: 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde, blongs to pyrimidines compound. name: 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde

Example 12Preparation of Compound 9Step 1 – Synthesis of compound 12A; 2-Fluoro-4-sulfonylmethyl aniline (0.104 g, 0.55 mmol) was cooled to -15 0C, then was diluted with TFA (0.55 mL, 7.4 mmol) and the resulting solution was allowed to stir for 30 minutes. Sodium triacetoxyborohydride (2.75 mmol) was then added portionwise and the resulting reaction was allowed to stir for an additional 30 minutes. To this reaction mixture was added a solution of compound 3 (0.1 g, 0.523 mmol) in dichloromethane (1.0 mL) and the resulting reaction was allowed to stir for 15 hours. The organic layer was collected and extracted with dichloromethane, and the dichloromethane was then washed with saturated aqueous sodium bicarbonate solution, dried over MgSO4, filtered and concentrated in vacuo. The residue obtained was purified using flash column chromatography on silica gel (30% acetone / hexanes) to provide compound 12 A (0.133 g, 69%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16019-33-3, 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; SCHERING CORPORATION; NEELAMKAVIL, Santhosh, Francis; BOYLE, Craig, D.; CHACKALAMANNIL, Samuel; GREENLEE, William, J.; WO2010/9195; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 16019-33-3, 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. 16019-33-3, name is 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde, molecular formula is C6H4Cl2N2O, 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.

(4,6-Dichloro-pyrimidin-5-yl)-acetadehyde (1.26 g, 6.37 mmol) was added to a solution of ci33-(1 ,1 -dioxo-1 -thiomorpholin-4-ylmethyl)-cyclobutylamine (Step N.3, 1 .21 g, 5.54 mmol) in diisopropylethylamine (1.98 ml 1 1.1 mmol) and ethanol (28 ml) at room temperature and the reaction mixture was then heated for 5 hours at reflux. After cooling to room temperature the reaction mixture was diluted with ethyl acetate, washed with aqueous sodium bicarbonate, then saturated brine, dried over sodium sulphate and evaporated. Purification by flash column chromatography, eluting with a gradient of methanol in DCM, gave the title compound. HPLC/MS tR 0.89 min, M+H 355.4 (Method X).

According to the analysis of related databases, 16019-33-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; IRM LLC; CHEN, Bai; FAIRHURST, Robin Alec; JIANG, Songchun; LU, Wenshuo; MARSILJE III, Thomas H.; MCCARTHY, Clive; MICHELLYS, Pierre-Yves; STUTZ, Stefan; WO2012/120469; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 16019-33-3, 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 16019-33-3 as follows.

Step 1 : 7-(4-Bromo-3-fluorophenyl)-4-chloro-6,7-dihydro-5H-pyrrolo[2,3- c/]pyrimidine (141) A round bottom flask was charged with 4-bromo-3-fluoroaniline (10.0 g, 52.5 mmol) and then cooled to -150C. Trifluoroacetic acid (50 ml.) was added to the above cold aniline while stirring the contents for 0.5 h. Na(OAc)3BH (15.9 g, 50 mmol) was added portion wise to the above mixture and stirred for additional 0.5 h. The aldehyde 209 (see example 118, step 1 , 7.85 g, 75 mmol) in CH2CI2 (15 ml.) was added to the above mixture. The resultant mixture was allowed to warm up to the ambient temperature and stirred for 24 h. The reaction mixture was concentrated under reduced pressure and the residue was poured into sat. NaHCO3 solution (250 ml.) and then the mixture was extracted with CH2CI2 (3 x 250 ml_). The combined organic layer was washed with brine (1 x 100 ml_), dried over sat. Na2SO4 and then concentrated under reduced pressure to afford crude material, which was recrystallized from CH2CI2 and MeOH to afford 8.65 g (53%) of the title prodcuct 141_as an off-white solid. 1H NMR (400 MHz, DMSO-c/6): delta 8.42 (s, 1 H), 7.88 and 7.86 (dd, J1 = 11.2 Hz, J2 = 2.8 Hz, 2 H), 7.51 (t, J = 8.0 Hz, 1 H), 7.36 and 7.34 (dd, J1 = 9.2 Hz, J2 = 2.4 Hz, 1 H), 4.11 (t, J = 8.8 Hz, 2 H), 3.22 (t, J = 8.4 Hz, 2 H); LCMS (ESI): m/z 329 (M + H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16019-33-3, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/8895; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia