Category: 111196-81-7

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. 111196-81-7, name is 2-Chloro-5-ethylpyrimidine, molecular formula is C6H7ClN2, 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. Safety of 2-Chloro-5-ethylpyrimidine

4-{2-[(5-Ethylpyrimidin-2-yl)amino]ethyl}phenol; Tyramine (5.52 g, 0.040 mol) in 40 ml of anhydrous DMF was treated with diisopropylethylamine (6.1 ml, 0.035 mol). After stirring at rt for 15 minutes, 2-chloro-5- ethylpyrimidine (4.25 ml, 035 mol) was added and the mixture heated at 80C for 14 hours. The solution was allowed to cool to room temperature and was partitioned between equal volumes of water and ethyl acetate. The aqueous phase was washed with ethyl acetate and the combined organic phases were dried over MgSO4 and concentrated. The residue was purified by flash chromatography eluting with 40% ethyl acetate-hexane to afford the title compound as a colorless solid 949 ; 58% 1H NMR (CDCl3) No. 1.20 (t, 3H, J=7.6); 2.46 (q, 2H, J=7.6); 2.83 (t, 2H, J=6.3); 3.515 (s, 1H); 3.63 (q, 2H, J=6.3); 5.14 (br s, 1H); 6.70 (d, 2H, J=8.4); 7.02 (d, 2H, J=8.3), 8.19 (s, 2H). MS: m/z 244 (M+1).

With the rapid development of chemical substances, we look forward to future research findings about 111196-81-7.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2003/74495; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 111196-81-7, 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.111196-81-7, name is 2-Chloro-5-ethylpyrimidine, molecular formula is C6H7ClN2, molecular weight is 142.59, as common compound, the synthetic route is as follows.

Step B: Preparation of 5-Ethyl-2-(4-(((lr,4r)-4-(2-fluoro-4- (methylsulfonyl)phenyl)cyclohexyloxy)methyl)piperidin-l-yl)pyrimidine (Compound 8).; A mixture of 4-(((lr,4r)-4-(2-fluoro-4- (methylsulfonyl)phenyl)cyclohexyloxy)methyl)piperidine hydrochloride (50.4 mg, 0.124 mmol), prepared in Step A above, 2-chloro-5-ethylpyrimidine (36 mu, 0.296 mmol), and triethylamine (52 mu, 0.373 mmol) in iPrOH (3 mL) was heated under microwave irradiation at 120 C for 2 h. The mixture was extracted with water and AcOEt. The organic phase was dried over MgS04, filtered, and concentrated. The residue was purified by silica gel flash column chromatography (hexane/ AcOEt gradient). Fractions containing the title compound (with 2- chloro-5-ethylpyrimidine as by product) were partly concentrated. The residue was treated with MTBE. Solid was filtered off, washed with additional MTBE, and dried under high vacuum to give the title compound (35.6 mg, 0.075 mmol, 60.3 % yield) as a white solid. Exact mass calculated for C25H34FN3O3S: 475.23, found: LCMS m/z = 476.2 [M+H]+; lU NMR (400 MHz, CDCI3) delta ppm 1.16-1.23 (m, 5H), 1.39-1.55 (m, 4H), 1.83-1.86 (m, 3H), 1.92-1.95 (m, 2H), 2.17-2.20 (m, 2H), 2.44 (q, = 7.6 Hz, 2H), 2.84-2.91 (m, 3H), 3.27 (s, 3H), 3.25-3.29 (m, 1H), 3.36 (d, = 6.1 Hz, 2H), 4.70-4.73 (m, 2H), 7.39-7.43 (m, 1H), 7.57-7.60 (m, 1H), 7.66-7.68 (m, 1H), 8.16 (s, 2H).

Statistics shows that 111196-81-7 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-ethylpyrimidine.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; HAN, Sangdon; LEHMANN, Juerg; THORESEN, Lars; WO2012/135570; (2012); 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.111196-81-7, name is 2-Chloro-5-ethylpyrimidine, molecular formula is C6H7ClN2, molecular weight is 142.59, as common compound, the synthetic route is as follows.Safety of 2-Chloro-5-ethylpyrimidine

Step 1. Preparation of 4-(5-ethylpyrimidin-2-yloxy)cyclohexanol To a stirred solution of cyclohexane-1,4-diol (2.03 g, 17.5 mmol) in DMF (17 mL) was added NaH (95% wt, 177 mg, 7.01 mmol) at 0 C. The mixture was stirred for 30 min at room temperature and 2-chloro-5-ethylpyrimidine (500 mg, 3.51 mmol) was added to the mixture. After being stirred for 16 hours at 70 C., the reaction mixture was diluted with EtOAc and water. The organic layer was washed by brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on SiO2 (Hex:EtOAc=1:1) to give the desired product (520 mg, 66%) as a colorless oil. 1H NMR (400 Hz, CDCl3) delta 1.24 (3H, t, J=7.6 Hz), 1.57-1.84 (5H, m), 2.03-2.20 (3H, m), 2.57 (2H, q, J=7.6 Hz), 3.78-3.82 (1H, m), 4.94-5.01 and 5.06-5.10 (1H, each m), 8.33 (2H, s). LC-MS m/z=222.8 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,111196-81-7, 2-Chloro-5-ethylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; CHEMIZON, A DIVISION OF OPTOMAGIC CO., LTD.; US2012/53180; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 111196-81-7, 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.111196-81-7, name is 2-Chloro-5-ethylpyrimidine, molecular formula is C6H7ClN2, molecular weight is 142.59, as common compound, the synthetic route is as follows.

General procedure: To a vial with septa containing tert-butyl 2-[(R)-5-bromo-2,3-dihydro-1H-inden-1-yl]-2,7-diazaspiro[3.5]nonane-7-carboxylate 3 (2.42 mmol) were added bis(pinacolato)diboron (2.61 mmol), potassium acetate (12.12 mmol), and Pd(dppf)Cl2 (0.039 mmol). The vial was purged with a stream of nitrogen, and anhydrous 1,4-dioxane (12 mL) was added. The resulting mixture was purged with nitrogen for three times, and the mixture was heated at 95 C for 1 h. The aryl halide 5 (2.61 mmol), Pd(dppf)Cl2 (0.062 mmol), and 9 ml of 2 M aqueous potassium carbonate solution (de-oxygenated by bubbling through N2 for 15 min) were added. The mixture was purged with N2 three times and heated at 95 C for 17 h. The mixture was cooled to room temperature and the organic layer was separated from the aqueous layer. The organic layer was filtered through a thin plug of silica gel, and rinsed with 5 mL of isopropyl alcohol followed by 5 mL of MeOH. The filtrate and the washings were concentrated under reduced pressure to give the crude product that was purified by silica gel chromatography eluting with a gradient of 010% MeOH in CH2Cl2 to give the desired product.

Statistics shows that 111196-81-7 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-ethylpyrimidine.

Reference:
Article; Fernando, Dilinie P.; Jiao, Wenhua; Polivkova, Jana; Xiao, Jun; Coffey, Steven B.; Rose, Colin; Londregan, Allyn; Saenz, James; Beveridge, Ramsay; Zhang, Yingxin; Storer, Gregory E.; Vrieze, Derek; Erasga, Noe; Jones, Ryan; Khot, Vishal; Cameron, Kimberly O.; McClure, Kim F.; Bhattacharya, Samit K.; Orr, Suvi T. M.; Tetrahedron Letters; vol. 53; 47; (2012); p. 6351 – 6354,4;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 111196-81-7, 2-Chloro-5-ethylpyrimidine, 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, 111196-81-7, blongs to pyrimidines compound. name: 2-Chloro-5-ethylpyrimidine

To a solution of5-[4-(methanesulfonyl)phenyl]-1-(piperidin-4-yl)-1H-pyrazolo[3,4-c]pyridine hydrochloride (0.153 mmol) in dimethylsulfoxide (DMSO) (1.5 ml) were added 2-chloro-5-ethylpyrimidine (44 mg, 0.309mmol) and Cs2CO3 (249 mg, 0.734 mmol). The mixture wasstirred at 180 C under microwaveirradiation for 20 min. The reaction was diluted with water andextracted with ethyl acetate. The combined organic layers were dried overanhydrous Mg2SO4 and reduced under pressure. The residuewas purified by silica gel column chromatography (0-50% EtOAc in hexanes) toafford 20 as a colorless solid (44mg, 62% yield).1H NMR (300 MHz, CDCl3): delta ppm1.22 (t, J = 7.5 Hz, 3 H), 2.14 -2.25 (m, 2 H), 2.26 – 2.45 (m, 2 H), 2.50 (q, J = 7.5 Hz, 2 H), 3.10 (s, 3 H), 3.13 – 3.25 (m, 2 H), 4.81 – 4.93(m, 1 H), 4.93 – 5.03 (m, 2 H), 8.02 – 8.08 (m, 2 H), 8.11 – 8.14 (m, 2 H),8.20 – 8.27 (m, 4 H), 9.14 (s, 1 H).MS ESI/APCI Dual m/z: 463 [M+1]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,111196-81-7, its application will become more common.

Reference:
Article; Matsuda, Daisuke; Kobashi, Yohei; Mikami, Ayako; Kawamura, Madoka; Shiozawa, Fumiyasu; Kawabe, Kenichi; Hamada, Makoto; Oda, Koji; Nishimoto, Shinichi; Kimura, Kayo; Miyoshi, Masako; Takayama, Noriko; Kakinuma, Hiroyuki; Ohtake, Norikazu; Bioorganic and Medicinal Chemistry Letters; vol. 26; 15; (2016); p. 3441 – 3446;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 111196-81-7, Adding some certain compound to certain chemical reactions, such as: 111196-81-7, name is 2-Chloro-5-ethylpyrimidine,molecular formula is C6H7ClN2, 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 111196-81-7.

Step B: Preparation of 4-((lr,4r)-4-((l-(5-Ethylpyrimidin-2-yl)piperidin-4- yl)methoxy)cyclohexyl)nicotinonitrile (Compound 58).; A mixture of 4-((lr,4r)-4-(piperidin-4-ylmethoxy)cyclohexyl)nicotinonitriledihydrochloride (26.5 mg, 71.17 muetaiotaomicron), 2-chloro-5-ethylpyrimidine (43 mu, 0.354 mmol), and potassium carbonate (50 mg, 0.362 mmol) in 1 ml iPrOH was heated under microwave irradiation at 100C for 3 h. Mixture was extracted with water and CH2C12. Organic phases were dried over MgS04, filtered, and concentrated. Residue was purified by biotage CC (Si02, hexane/AcOEt gradient). Fractions containing product were concentrated and residue was re- purified by HPLC (CH3CN/H20 gradient + 0.1% TFA). Fractions containing product were partly concentrated and residue was extracted with 1 M NaOH and CH2C12. Organic phases were dried over MgS04, filtered, and concentrated to give 4-((lr,4r)-4-((l-(5-ethylpyrimidin-2- yl)piperidin-4-yl)methoxy)cyclohexyl)nicotinonitrile (22.1 mg, 54.50 muetaiotaomicron, 76.6 %) as a white solid. Exact mass calculated for C24H3iN50: 405.25, found: LCMS m/z = 406.4 (M+H+); lU NMR (400 MHz, CDC13) delta ppm 1.19-1.29 (m, 5H), 1.41-1.62 (m, 4H), 1.83-1.89 (m, 3H), 1.98- 2.04 (m, 2H), 2.20-2.26 (m, 2H), 2.47 (q, = 7.6, 2H), 2.86-2.97 (m, 3H), 3.27-3.35 (m, 1H), 3.38 (d, = 6.3 Hz, 2H), 4.71-4.77 (m, 2H), 7.28 (d, = 5.3 Hz, 1H), 8.18 (s, 2H), 8.71 (d, = 5.3 Hz, 1H), 8.82 (s, 1H).

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. 111196-81-7, 2-Chloro-5-ethylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; HAN, Sangdon; LEHMANN, Juerg; THORESEN, Lars; WO2012/135570; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 111196-81-7, 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 111196-81-7 as follows.

Step D: Preparation of 4-(l-(5-Ethylpyrimidin-2-yl)piperidin-4-yloxy)-5-fluoro-6- (2-methyl-6-(methylsulfonyl)pyridin-3-yloxy)pyrimidine.To a solution of 5-fluoro-4-(2-methyl-6-(methylsulfonyl)pyridin-3-yloxy)-6-(piperidin- 4-yloxy)pyrimidine hydrochloride (50.0 mg, 0.119 mmol) and 2-chloro-5-ethylpyrimidine (17.0 mg, 0.119 mmol) in IPA (2 mL) was added triethylamine (0.166 mL, 1.194 mmol). The reaction mixture was heated at 100 C under microwave irradiation for 3 h and then concentrated under reduced pressure. The residue was taken up in EtOAc and washed with water. The EtOAc layer was dried over anhydrous Na2S04, filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography to give the title compound as a white solid (21.0 mg, 36%). Exact mass calculated for C22H25FN6O4S: 488.2, found: LCMS m/z = 489.4 [M+H]+; lU NMR (400 MHz, CDC13) delta ppm 1.14 (t, = 8.0 Hz, 3H), 1.69-1.77 (m, 2H), 2.06-2.11 (m, 2H), 2.45 (q, = 8.0 Hz, 2H), 2.47 (s, 3H), 3.31 (s, 3H), 3.49-3.55 (m, 2H), 4.20-4.26 (m, 2H), 5.43-5.47 (m, 1H), 8.01 (d, = 8.0 Hz, 1H), 8.04 (d, = 8.0 Hz, 1H), 8.25 (s, 1H), 8.27 (s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,111196-81-7, its application will become more common.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; WO2012/145604; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 111196-81-7 ,Some common heterocyclic compound, 111196-81-7, molecular formula is C6H7ClN2, 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.

A screw-cap vial was charged with benzamide (121 mg, 1.00 mmol), Cs2CO3 (456 mg, 1.40 mmol), Xantphos (87 mg, 0.15 mmol), Pd2(dba)3 (46 mg, 0.050 mmol), 2-chloropyrimidine (137 mg, 1.20 mmol), and 1,4-dioxane (2 mL). The mixture was sparged with nitrogen for 3 min, stirred for 16 h at 100 C, and cooled to room temperature. The residue was diluted with dichloromethane, filtered through celite, and concentrated. The crude product was purified by silica gel flash chromatography (40-100% ethylacetate/hexanes) to provide N-(pyrimidin-2-yl)benzamide (188 mg, 0.85 mmol, 94% yield) as an amorphous solid (Table 1, entry 8).

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. 111196-81-7, 2-Chloro-5-ethylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Vimolratana, Marc; Simard, Jillian L.; Brown, Sean P.; Tetrahedron Letters; vol. 52; 9; (2011); p. 1020 – 1022;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 111196-81-7 , The common heterocyclic compound, 111196-81-7, name is 2-Chloro-5-ethylpyrimidine, molecular formula is C6H7ClN2, 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.

General procedure: In a reaction vial designed for microwave heating, the considered alkoxypyrazole (2 mmol), the considered halogenated heteroaryl (2.2 mmol) and cesium carbonate (2.8 mmol) were stirred in dimethylformamide or acetonitrile (3 mL) as specified in the examples. This was heated using a microwave at a temperature between 120 C and 180 C for the individually specified duration. The resulting suspension was diluted in water, extracted with ethyl acetate and the organic layer was washed with brine, dried over magnesium sulfate and concentrated to dryness. The residue was further purified as described below.

The synthetic route of 111196-81-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INSTITUT PASTEUR; JANIN, Yves-Louis; GUILLOU, Sandrine; LUCAS-HOURANI, Marianne; MUNIER-LEHMANN, Helene; NOEL, Anne; SALANOUVE, Elise; TANGY, Frederic; VIDALAIN, Pierre-Olivier; WO2015/155680; (2015); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 111196-81-7, Adding some certain compound to certain chemical reactions, such as: 111196-81-7, name is 2-Chloro-5-ethylpyrimidine,molecular formula is C6H7ClN2, 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 111196-81-7.

To a reaction flask was added compound18(700 mg, 2.19 mmol) and 2-chloro-5-ethylpyrimidine (621 mg, 4.37 mmol) in one-portion in the presence of anhydrous DMF. After stirring at room temperature for 5 min, to the resulting clear solution was added anhydrous K2CO3(453 mg, 3.28 mmol) in one-portion. The reaction flask immersed in a pre-heated oil-bath (90) and the reaction mixture was stirred at 90for 4 h and cooled to room temperature. To the reaction mixture at room temperature under vigorous stirring and H2O was added slowly dropwise over 30 min to give an off-white slurry. After the addition was finished, the resulting slurry was stirred at room temperature for additional 10 min. The precipitate was filtered and then rinsed with H2O (2 x 30 mL) and the precipitate was dissolved in EtOAc, and washed with H2O (2 x 30 mL). The organic layer was collected, dried over anhydrous Na2SO4, filtered, concentrated and purifiedby silica gel column chromatography using 40% EtOAc in hexanes to afford compound19(680 mg, 73%).1H-NMR (CDCl3, 300 MHz) delta 9.87 (1H, s, CHO), 8.19 (2H, s, pyrimidine), 7.64 (2H, d,J= 6.9 Hz, Ar), 7.29 (1H, s, thiazole), 7.18 (1H, t,J= 6.9 Hz, Ar), 5.32 (2H, s, OCH2), 4.81 (2H, d,J= 6.0 Hz, CH2), 3.33 (1H, t,J= 12.3 Hz, CH), 3.25 (2H, t,J= 9.3 Hz, CH2), 2.46 (2H, q,J= 9.3 Hz, CH2), 2.19 (2H, d,J= 11.7 Hz, CH2), 1.79 (2H, dq,J= 12.0 Hz, 2.7 Hz, CH2), 1.22 (3H, t,J= 9.0 Hz, CH3).

According to the analysis of related databases, 111196-81-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kim, Hyojin; Cho, Suk Joon; Yoo, Minjin; Kang, Seung Kyu; Kim, Kwang Rok; Lee, Hwan Hee; Song, Jin Sook; Rhee, Sang Dal; Jung, Won Hoon; Ahn, Jin Hee; Jung, Jae-Kyung; Jung, Kwan-Young; Bioorganic and Medicinal Chemistry Letters; vol. 27; 23; (2017); p. 5213 – 5220;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia