Category: 16019-33-3

Electric Literature 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.

Step 5:To a stirred solution of 2-(4,6-dichloropyrimidin-5-yl)acetaldehyde (600 mg) in dry MeCN (10 mL), methyl hydrazine (154 mg) and sodium acetate (514 mg) were added. The reaction mixture was stirred at room temperature for 3 hours and solvents were removed under reduced pressure. The resulting oil was diluted with ethyl acetate(50 mL), washed with water (10 mL) and brine (10 mL). The organic layer was dried over anhydrous a2S04 and concentrated. The resulting crude product was purified by column chromatography using EtOAc/CHCi3 (0.4:9.6) as eluent to afford 5-chloro-l- methyl-l,4-dihydropyridazino[3,4-d]pyrimidine (310 mg) as white solid. lH NMR (DMSO-d6): delta 3.34 (s, 3H), 3.53-3.54 (d, 2H), 6.91-6.93 (t, 1H), 8.38 (s, 1H).

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; BRISTOL-MYERS SQUIBB COMPANY; WANG, Tao; KADOW, John, F.; MEANWELL, Nicholas, A.; HAMANN, Lawrence, G.; WO2013/138436; (2013); A1;,
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Reference of 16019-33-3 ,Some common heterocyclic compound, 16019-33-3, 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.

tert-Butylamine (2.1 1 mL, 20.0 mmol) was added to (4,6-dichloropyrimidin-5- yl)acetaldehyde (1 .91 g, 10.0 mmol) in ethanol (100 mL). The mixture was heated at 80C for 16 hours. The reaction mixture was evaporated in vacuo then the residue was diluted with water (100 mL) and extracted with ethyl acetate (3 x 100 mL). The combined organic extracts were evaporated in vacuo and the crude material was purified by silica gel column chromatography eluting with a gradient of Heptanes:EtOAc 100:0 to 60:40 to afford the title compound as a yellow liquid in 77% yield, 1 .61 g. 1H NMR (400 MHz, DMSO-d6): delta ppm 1 .75 (s, 9H), 6.60 (d, 1 H), 7.79 (d, 1 H), 8.63 (s, 1 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; PFIZER LIMITED; ANDREWS, Mark, David; BAGAL, Sharanjeet, Kaur; BROWN, David, Graham; GIBSON, Karl, Richard; OMOTO, Kiyoyuki; RYCKMANS, Thomas; SABNIS, Yogesh; SKERRATT, Sarah, Elizabeth; STUPPLE, Paul, Anthony; WO2014/53967; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 16019-33-3 ,Some common heterocyclic compound, 16019-33-3, 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.

tert-Butylamine (2.1 1 mL, 20.0 mmol) was added to (4,6-dichloropyrimidin-5- yl)acetaldehyde (1 .91 g, 10.0 mmol) in ethanol (100 mL). The mixture was heated at 80C for 16 hours. The reaction mixture was evaporated in vacuo then the residue was diluted with water (100 mL) and extracted with ethyl acetate (3 x 100 mL). The combined organic extracts were evaporated in vacuo and the crude material was purified by silica gel column chromatography eluting with a gradient of Heptanes:EtOAc 100:0 to 60:40 to afford the title compound as a yellow liquid in 77% yield, 1 .61 g. 1H NMR (400 MHz, DMSO-d6): delta ppm 1 .75 (s, 9H), 6.60 (d, 1 H), 7.79 (d, 1 H), 8.63 (s, 1 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; PFIZER LIMITED; ANDREWS, Mark, David; BAGAL, Sharanjeet, Kaur; BROWN, David, Graham; GIBSON, Karl, Richard; OMOTO, Kiyoyuki; RYCKMANS, Thomas; SABNIS, Yogesh; SKERRATT, Sarah, Elizabeth; STUPPLE, Paul, Anthony; WO2014/53967; (2014); 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. 16019-33-3, name is 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde. A new synthetic method of this compound is introduced below., Recommanded Product: 16019-33-3

To a solution of 2-(4,6-dichloropyrimidin-5-yl)acetaldehyde (2.80 g, 14.66 mmol) and ((1S,4S)-4-aminocyclohexyl)methanol (Step AS.3, 14.66 mmol) in anhydrous EtOH (30 mL) was added DIEA. The reaction was stirred in a sealed vial at 60 C for 20 h.The reaction was diluted with EtOAc (150 mL), washed with water (10 mL), saturated aqueous NaCI (10 mL), dried over Na2S04 and evaporated. The residue was purified by flash chromatography (Si02, EtOAc: hex/0- 100%) to give the title compound as a yellow solid. MS m/z 266.1 (M+H+) (Method M).

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, 16019-33-3, 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde.

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;,
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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. Formula: C6H4Cl2N2O

Step 1: Synthesis of 7-(tert-butyl)-4-chloro-7H-pyrrolo[2,3-d]pyrimidine A mixture solution of 29.3 g of 2-(4,6-dichloropyrimidin-5-yl)acetaldehyde, 13.4 g of tert-butylamine, and 29.7 g of N,N-diisopropylethylamine in 200 mL of ethanol was stirred with heating under reflux for 2 hours. After cooling, the reaction mixture was concentrated. The residue was diluted with ethyl acetate, washed with water and subsequently washed with a saturated aqueous sodium chloride solution. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The obtained residue was purified by silica gel chromatography, thereby obtaining 21.5 g of the title compound. Physical Properties: m/z [M+H]+ 210.0.

With the rapid development of chemical substances, we look forward to future research findings about 16019-33-3.

Reference:
Patent; TAIHO PHARMACEUTICAL CO., LTD.; MIYAZAKI, Isao; SHIMAMURA, Tadashi; KATO, Masanori; FUJITA, Hidenori; IGUCHI, Satoru; (161 pag.)US2018/9818; (2018); A1;,
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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. name: 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde

Step 1 : lambda/-[2-(4,6-Dichloro-5-pyrimidinyl)ethyl]-5-fluoro-2-pyridinamine (187)A round bottom flask was charged with 2-amino-5-fluoropyridine (0.323 g, 2.88 mmol) and cooled to -15C. Trifluoroacetic acid (2.5 ml_, 32.2 mmol) was added and the solution was stirred for 10 minutes at -15C. Na(OAc)3BH (0.89 g, 4.2 mmol) was added to the reaction mixture and stirred for 10 minutes. A solution of 209 (0.5 g, 2.62 mmol) in CH2CI2 (2.0 ml.) was added dropwise and the reaction mixture was stirred at -15C for 30 minutes, then stirred at RT for 15 h. Mixture was concentrated under reduced pressure, diluted with 10% NaHCO3, extracted with CH2CI2 (3 x 10 ml_), dried over MgSO4, filtered, and concentrated under reduced pressure to afford the crude material, which was purified by SiO2 flash column chromatography to give 0.17 g of the title compound 187 and 4-chloro-7-(5-fluoro-2-pyridinyl)-6,7-dihydro-5/-/-pyrrolo[2,3- c/]pyrimidine as an inseparable mixture . 1H NMR (400 MHz, CDCI3): delta 8.62 (s, 1 H), 7.92 (d, J = 2.68 Hz, 1 H), 7.14 – 7.23 (m, 1 H), 6.37 (dd, J1 = 9.10 Hz, J2 = 3.39 Hz, 1 H), 4.60 (br. s, 1 H), 6.67 (q, J = 6.54 Hz, 2 H), 3.24 (t, J = 6.87 Hz, 2 H); LCMS (APCI): m/z 287 (M + H)+.

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

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

Reference of 16019-33-3, Adding some certain compound to certain chemical reactions, such as: 16019-33-3, name is 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde,molecular formula is C6H4Cl2N2O, 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 16019-33-3.

2-(4,6-dichloropyrimidin-5-yl)acetaldehyde was dissolved in ethanol (0.55M). Triethylamine was then added to the reaction mixture (2 equiv) and stirred for ten minutes at room temperature. Tert-butylamine was then added (2 equiv) to the reaction mixture and heated (reflux, 90 C) overnight. The reaction mixture was then evaporated in vacuo. The crude mixture was then dissolved in 1 : 1 deionized water ethyl acetate and the organic layer was collected and concentrated. The organic extract was then purified using FCC (gradient of hexanes:ethyl acetate (95:5 to 80:20) to yield a yellow oil in 59.5% Yield. NMR matched literature (Andrews et al, Patent WO2012137089 Al, Prep 5). NMR (400 MHz, CDCh) delta 8.57 (s, 1H), 7.35 (d, J= 3.7 Hz, 1H), 6.49 (d, J= 3.7 Hz, 1H), 1.75 (s, 9H).

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. 16019-33-3, 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SAN DIEGO STATE UNIVERSITY RESEARCH FOUNDATION; GUSTAFSON, Jeffrey L.; TOENJES, Sean Thomas; MADDOX, Sean M.; (69 pag.)WO2018/237134; (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, 16019-33-3, blongs to pyrimidines compound. name: 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde

Step K.1 : Benzoic acid c s-3-(4-chloro-pyrrolo[2,3-d]pyrimidin-7-yl)-cyclobutylmethyl ester A mixture of (4,6-dichloro-pyrimidin-5-yl)-acetaldehyde (Astatech, 1.40 g, 7.31 mmol), benzoic acid 3-amino-cyclobutylmethyl ester (prepared as described in Org. Process Res. Dev. 2007, 11, 825-835., 1.5 g, 7.31 mmol), diisopropylethylamine (0.95 g, 7.31 mmol) and etha- nol (15 ml) were heated at reflux for 5.5 hours under an argon atmosphere. The reaction mix- ture was evaporated, taken up in THF (10 ml), aqueous HCI (4 ml, 4M) added and stood at room temperature for 1 hour. The volume of the mixture was then reduced under vacuum, made neutral with aqueous sodium bicarbonate solution, extracted 3X with DCM, the organic layers dried over sodium sulphate and evaporated. Purification by flash column chromatography, eluting with a DCM / EtOAc gradient gave the title compound. HPLC/MS tR 1.52 min, M+H 342.1 (Method X).

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; NOVARTIS AG; IRM LLC, a Delaware Limited Liability Company; CHEN, Bei; FAIRHURST, Robin, Alec; FLOERSHEIMER, Andreas; FURET, Pascal; JIANG, Songchun; LU, Wenshuo; MARSILJE, Thomas, H.; VAUPEL, Andrea; WO2011/64211; (2011); A1;,
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Related Products of 16019-33-3, Adding some certain compound to certain chemical reactions, such as: 16019-33-3, name is 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde,molecular formula is C6H4Cl2N2O, 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 16019-33-3.

A mixture of compound 7 (20.0 g, 0.1 mol), triethyl orthoformate (18.6 g, 0.12 mol), and TsOH (1.0 g, 5.8 mmol) in EtOH (100 ml) was stirred at 40C for 2 h. After completion of the reaction, aqueous Na2CO3 was added to the mixture to adjust pH to 8. The solvent was removed under reduced pressure and the residue extracted with EtOAc (300 ml), washed with water (100 ml). The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the residue that was purified by column chromatography on silica gel (eluent petroleumether – EtOAc, 5:1). Yield 25.0 g (90%), colorless oil. IR spectrum, nu, cm-1: 2987, 1546, 1518, 1123, 1068, 785. 1H NMR spectrum (CDCl3), delta, ppm (J, Hz): 8.62 (1H, s,H-2); 4.80 (1H, t, J = 5.8, CH); 3.74-3.66 (2H, m,CH2CH3); 3.48-3.41 (2H, m, CH2CH3); 3.25 (2H, d, J = 5.7,CH2); 1.13 (6H, t, J = 7.0, CH2CH3). 13C NMR spectrum (CDCl3), delta, ppm: 162.7; 155.8; 132.5; 129.2; 100.9; 62.9;35.4; 15.2. Found, m/z: 287.0323 [M(35Cl)+Na]+.C10H14Cl2N2NaO2. Calculated, m/z: 287.0325. Found, m/z:289.0295 [M(35Cl,37Cl)+Na]+. Calculated, m/z: 289.0296.

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. 16019-33-3, 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhang, Yu-Liu; Xu, Cheng-Tao; Liu, Ting; Zhu, Yong; Luo, Yu; Chemistry of Heterocyclic Compounds; vol. 54; 6; (2018); p. 638 – 642; Khim. Geterotsikl. Soedin.; vol. 54; 6; (2018); p. 638 – 642,5;,
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Related Products of 16019-33-3, 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.16019-33-3, name is 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde, molecular formula is C6H4Cl2N2O, molecular weight is 191.02, as common compound, the synthetic route is as follows.

To the stirred solution of (R)-3-amino-pyrrolidine-1 -carboxylic acid tert-butyl ester (CAS 147081-49-0; 4.68 g, 25.1 mmol, 1.0 eq) and EtOH (50 mL) was added N,N- diisopropylamine (4.30 mL, 25.1 mmol, 1.0 eq) and 4,6-dichloro-pyrimidin-5-yl)-acetaldehyde (CAS 16019-33-3; 4.80 g, 25.1 mmol,). The reaction mixture was stirred for 8h at reflux temperature and then concentrated. The residue was dissolved in THF (37.5 mL) and HCI 4M (12.5 mL) was added at 0 C and stirred for an additional hour at 0 C. The reaction mixture was partitioned between Na2C03 1 M and EtOAc. The combined organic layers were washed with brine, dried (Na2S0 ), filtered and concentrated. The residue was purified by silica gel column chromatography (EtOAc – nheptane 1 :1 ) to afford 6.70 g of the title compound as a yellow oil: HPLC-MS: M+H = 323.4 (Rt = 1.27) (Method X): TLC; R, = 0.19 (EtOAc – n heptane 1 :2).

Statistics shows that 16019-33-3 is playing an increasingly important role. we look forward to future research findings about 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde.

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;,
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