Day: March 17, 2021

Electric Literature of 705263-10-1 , The common heterocyclic compound, 705263-10-1, name is 6-Bromopyrazolo[1,5-a]pyrimidine, molecular formula is C6H4BrN3, 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.

Example 1 6-Phenylethynyl-pyrazolo[1,5-a]pyrimidine Bis-(triphenylphosphine)-palladium(II) dichloride (27 mg, 0.04 mmol) was dissolved in 1 ml of THF. 6-Bromo-pyrazolo[1,5-a]pyrimidine (150 mg, 0.76 mmol) and phenylacetylene (130 mul, 1.21 mmol) were added at room temperature. Triethylamine (310 mul, 2.3 mmol), triphenylphosphine (6 mg, 0.023 mmol) and copper(I) iodide (4 mg, 0.023 mmol) were added and the mixture was stirred for 2 hours at 65 C. The reaction mixture was cooled and extracted with saturated NaHCO3 solution and two times with a small volume of dichloromethane. The crude product was purified by flash chromatography by directly loading the dichloromethane layers onto a silica gel column and eluting with heptane:ethyl acetate 100:0->50:50. The desired compound was obtained as a yellow solid (150 mg, 90% yield), MS: m/e=220.3 (M+H+).

The synthetic route of 705263-10-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Green, Luke; Guba, Wolfgang; Jaeschke, Georg; Jolidon, Synese; Lindermann, Lothar; Stadler, Heinz; Vieira, Eric; US2011/152257; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 54326-16-8 ,Some common heterocyclic compound, 54326-16-8, molecular formula is C4H3ClN2O, 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.

EXAMPLE 12 5-Chloro-1-(1-oxo-1-phenylprop-2-yl)pyrimidin-2-one A solution of 5-chloropyrimidin-2-one (394 mg) and alpha-bromopropiophenone (0.5 ml) in triethylamine (1 ml) and ethanol (20 ml) was stirred at ambient temperature for 2.75 hours. The solution was evaporated and the residue was triturated with water (50 ml) giving an oily solid. This was extracted with ethyl acetate (3*50 ml). The combined extracts were washed with brine (50 ml), dried (MgSO4) and evaporated to a gum. This was crystallized from acetone-petrol (b.p. 40-60) to give the title pyrimidinone (306 mg,); m.p. 125-127; lambdamaxEtOH 232 nm (epsilon 15400), 245 nm (epsilon 15480), 335 nm (epsilon 3970).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,54326-16-8, its application will become more common.

Reference:
Patent; Glaxo Group Limited; US4636509; (1987); A;,
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. 1152475-50-7, name is 2-Chloro-7-iodo-5H-pyrrolo[3,2-d]pyrimidine. A new synthetic method of this compound is introduced below., Formula: C6H3ClIN3

To a stirred solution of 2-chloro-7-iodo-5H-pyrrolo[3,2-d]pyrimidine (110 mg, 0.39 mmol) in DCM (5 ml) was added tetrabutylammonium bromide (19 mg, 0.06 mmol), NaOH (1 ml, 2M) and MeI (47 mul, 0.47 mmol) were added and the mixture was stirred for 16 hours at room temperature. Water, DCM and EtOAc were added and the phases were separated. Concentration by evaporation followed by trituration using Et2O gave 110 mg (94%) of the title compound. LC/MS (20-100% CH3CN:0.05% HCOOH(aq) gradient over 5 min): 3.07 min. 294 M+H.

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, 1152475-50-7, 2-Chloro-7-iodo-5H-pyrrolo[3,2-d]pyrimidine.

Reference:
Patent; PFIZER INC.; Schnute, Mark Edward; Wennerstal, Goeran Mattias; Blinn, James Robert; Kaila, Neelu; Kiefer, JR., James Richard; Mente, Scot Richard; Kurumbail, Ravi G.; Meyers, Marvin Jay; Thorarensen, Atli; Xing, Li; Zapf, Christoph Wolfgang; Zamaratski, Edouard; Flick, Andrew Christopher; Jones, Peter; (77 pag.)US2016/46597; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 13036-50-5, Adding some certain compound to certain chemical reactions, such as: 13036-50-5, name is 2-Chloro-4-phenylpyrimidine,molecular formula is C10H7ClN2, 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 13036-50-5.

To the obtained 2-chloro-4-phenylpyrimidine was added concentrated hydrochloric acid (~ 10 N) and stirred well. The homogeneous mixture was refluxed for 1 hour. The reaction mixture was poured into 10% aqueous sodium carbonate solution. The white precipitate was filtered off and dried to give a white solid. TLC was observed at R f: 02 (chloroform: methanol (9.5: 0.5))

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. 13036-50-5, 2-Chloro-4-phenylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Industry & Academic Cooperation in Chungnam National University (IAC); Jung, Sang-Hun; Woo, Sun-Hee; Kim, Sang- Kyum; Jeon, Eun-Seok; Lee, Yu-Jung; Meunikam, Manoj; Jalani, Hiteshkumar; Sharma, Niti; (205 pag.)KR2016/108281; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 289042-12-2, 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. 289042-12-2, name is tert-Butyl 2-((4R,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate, molecular formula is C29H40FN3O6S, 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.

To a 3 L four-necked flask was added 1.5 L of absolute ethanol and 128.0 g of 6 – [(1E) -2- [4- (4-fluorophenyl) -6-isopropylYl-2- [methyl (methylsulfonyl) amino] -5-pyrimidine] vinyl] -2,3-dimethyl-1,3-dioxacyclohexane-4-acetic acid tert-butyl ester(Compound III). After stirring, 450 g of dilute hydrochloric acid solution with a mass fraction of 3.6% was added dropwise, stirred at room temperature for 4 to 6 hours, and TLC was monitored until compound III disappeared. After completion of the reaction, 320 g of a sodium hydroxide solution having a mass fraction of 4% was added dropwise to the reaction system and stirring was continued for 4 to 6 hours. The reaction was continued until the first stage of the dihydroxy ester intermediate was completely disappeared (residual?0.5%). The ethanol was then concentrated under reduced pressure, and then 2 L of purified water was added to the system. After stirring, the mixture was extracted twice with methyl t-butyl ether and the aqueous phase was concentrated to no organic solvent residue. The mass fraction was then slowly added to the resulting aqueous solution For 10% of the calcium acetate solution 420g, a white solid precipitation, after the drop is completed, continue stirring 4 to 6 hours, filtration, filter cake with 2L purified water beating 1 times, dry, filter cake vacuum drying, Statin calcium A, the yield was 87.0%, content ? 99.0%, purity(HPLC) ?99.0%, single maximum impurity ? 0.5%, product ee value ? 99.9%.

According to the analysis of related databases, 289042-12-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Anhui Mei Nuohua Pharmaceutical Chemical Co., Ltd.; Shi Jianxiang; Pan Qijiao; Ding Maohua; Gong Daoxin; Zhu Guosheng; (14 pag.)CN106674281; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 26032-72-4, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 26032-72-4, name is 2,4-Dichloro-6-phenylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Under nitrogen, Compound A was dissolved in tetrahydrofuran / toluene (5: 1) and 1.2 equivalents of Compound B was added. 4.4 equivalents of potassium carbonate was dissolved in distilled water (DI water) and 0.05 equivalent of Pd (0) was added. The reaction mixture was refluxed at 80 DEG C and stirred for 24 hours to terminate the reaction. After extraction with an organic solvent, the organic solvent was removed. Through column re-precipitation, Compound C was obtained.

According to the analysis of related databases, 26032-72-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LG Display Co., Ltd.; Yoon Gyeong-jin; Noh Hyo-jin; Song In-beom; Baek Jeong-eun; (23 pag.)KR2019/70090; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 26452-81-3 , The common heterocyclic compound, 26452-81-3, name is 4-Chloro-6-methoxypyrimidine, molecular formula is C5H5ClN2O, 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 mixture of methyl 3-ethoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylate (10520 mg, 30 mmol), 4-chloro-6-methoxypyrimidine (4645 mg, 31.5 mmol), dichloro(1,V-bis(diphenylphosphino) ferrocene) palladium (II) dichloromethane adduct) (2449 mg, 3 mmol) and potassium phosphate tribasic monohydrate (20719 mg, 90 mmol) in water (4 mL) and DMF (150 mL) is degassed for 20 min under a nitrogen stream, then stirred at RT for 1 h15. The RM is filtered through celite, the filtrate is concentrated under vacuum, the residue is partitioned between water and EtOAc. The organic layer is further washed with brine, dried over MgS04, filtered and concentrated. Purification by FC (heptane/EtOAc, from 1 :0 to 0:1) affords the title compound as a yellow solid (7.87 g, 89percent). LC-MS B: tR = 0.93 min; [M+H]+ = 295.18.

The synthetic route of 26452-81-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; BOSS, Christoph; CORMINBOEUF, Olivier; FRETZ, Heinz; LYOTHIER, Isabelle; POZZI, Davide; RICHARD-BILDSTEIN, Sylvia; SIENDT, Herve; SIFFERLEN, Thierry; (190 pag.)WO2018/210987; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 7355-55-7 ,Some common heterocyclic compound, 7355-55-7, molecular formula is C6H6N4O, 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.

Example IB4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine A suspension of Example 1A (25 g, 0.16 mol) in POCI3 (250 ml) was heated under reflux for 3 hours. After cooling to room temperature, excess of POCI3 was removed under vacuum. Ice water (250 ml) was added and the resulting solid was filtered off. The pH of the filtrate was adjusted to pH = 2 with aqueous ammonia. After leaving the precipitate in an ice bath, the mixture was filtered off, and was washed with cold water (25 ml) and cold ether (25 ml) consecutively. The solid was dried under vacuum to give the title compound. MS (ESI) (+) m/z 169.7 (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,7355-55-7, its application will become more common.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT LABORATORIES TRADING (SHANGHAI) COMPANY, LTD.; VAN CAMP, Jennifer; XU, Xiangdong; OSUMA, Augustine, Toby; GREGG, Robert; LONGENECKER, Kenton, L.; WO2012/45195; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1088994-22-2 ,Some common heterocyclic compound, 1088994-22-2, molecular formula is C12H10N2O2, 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.

Compound 3-1 (100 mg, 0.26 mmol), compound 5-1 (58 mg, 0.28 mmol), HATU (150 mg, 0.39 mmol) and DIEA (124 mg, 0.96 mmol) were dissolved in 5 mL of DMF, and the mixture was stirred under room temperature for 3 hours. The reaction mixture was poured into aqueous saline and extracted with ethyl acetate (10 mL x 3). The organic phase was combined and washed with water (10 mL x 2) and saturated NaCl solution (10 mL x 2), dried, filtered and concentrated to give a crude product. The crude product was separated by preparative HPLC to obtain compound 7-1 (30 mg, white solid, yield: 20%). 1H NMR (400 MHz, MeOD) delta= 8.78 (dd, J=4.9, 9.7 Hz, 2H), 8.17 (d, J=8.2 Hz, 0.5H), 8.11 (d, J=7.9 Hz, 0.5H), 8.01 (d, J=3.1 Hz, 0.5H), 7.75 (br. s., 0.5H), 7.57-7.50 (m, 0.5H), 7.43 (d, J=8.2 Hz, 0.5H), 7.38-7.31 (m, 2H), 7.26 (s, 0.4H), 7.13 (s, 0.6H), 6.86 (dd, J=3.5, 9.0 Hz, 0.5H), 6.36 (dd, J=3.5, 9.0 Hz, 0.5H), 4.77-4.72 (m, 0.5H), 4.21-4.11 (m, 1.5H), 3.78 (br. s., 1H), 2.52 (br. s., 1H), 2.46 (s, 1.5H), 2.35 (s, 1.5H), 2.09-1.95 (m, 2H), 1.91-1.37 (m, 7H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1088994-22-2, its application will become more common.

Reference:
Patent; Shanghai Haiyan Pharmaceutical Technology Co. Ltd.; Yangtze River Pharmaceutical Group Co., Ltd.; HE, Haiying; WU, Songliang; ZHANG, Yang; MA, Biao; CHEN, Yuan; WANG, Yuhe; CHEN, Shuhui; LV, Qiang; LAN, Jiong; LIU, Xing; (54 pag.)EP3115362; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 39906-04-2, 4,6-Dichloro-2-methylpyrimidin-5-amine, 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, 39906-04-2, blongs to pyrimidines compound. HPLC of Formula: C5H5Cl2N3

2-Methyl-4,6-dichloro-5-aminopyrimidine (Aldrich, 1.05 g) and ammonium hydroxide(3.0 mL, J.T. Baker, Phillipsburg, NJ, 28.0% – 30.0 %) were placed in a microwave vial. The vial was sealed and heated in a CEM microwave reactor (CEM Corporation, Matthews, NC) at120 0C and 40 Watts for 25 minutes. The reaction mixture was cooled to room temperature. This procedure was repeated a total of nine times using the following amounts of 2-methyl-4,6- dichloro-5-aminopyrimidine under the same reaction conditions:Run 2: 1.027 g. 2.5 mL ammonium hydroxide.Run 3: 1.034 g, 2.5 mL ammonium hydroxide.Run 4: 1.118 g, 2.6 mL ammonium hydroxide. Run 5 : 1.117 g, 2.5 mL ammonium hydroxide.Run 6: 1.149 g, 2.7 mL ammonium hydroxide.Run 7: 1.264 g, 2.6 mL ammonium hydroxide.Run 8: 1.106 g, 2.6 mL ammonium hydroxide.Run 9: 1.075 g, 2.7 mL ammonium hydroxide.All the runs were combined and concentrated to give 6-chloro-2-methylpyrimidine-4,5-diamin. MS (ESI pos. ion) m/z: 159. Calcd. MS: 158.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,39906-04-2, its application will become more common.

Reference:
Patent; AMGEN INC.; BODE, Christiane; BOEZIO, Alessandro; CHENG, Alan, C.; CHOQUETTE, Deborah; COATS, James, R.; COPELAND, Katrina, W.; HUANG, Hongbing; LA, Daniel; LEWIS, Richard; LIAO, Hongyu; POTASHMAN, Michele; STELLWAGEN, John; YI, Shuyan; NORMAN, Mark; STEC, Markian; PETERSON, Emily, A.; GRACEFFA, Russell; WO2010/132598; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia