63155-11-3 | Pyrimidines

Xiao, Ke’s team published research in ChemistrySelect in 2018 | CAS: 63155-11-3

Ethyl 2-(pyrimidin-2-yl)acetate(cas: 63155-11-3) is a member of pyrimidine. Pyrimidine derivatives are an important class of N-heterocycles. They are well-known for their wide spectrum of promising biological activities such as antitumors, bactericidals, and fungicidal.Formula: C8H10N2O2

In 2018,ChemistrySelect included an article by Xiao, Ke; Zhu, Congjun; Lin, Maohua; Song, Chuanjun; Chang, Junbiao. Formula: C8H10N2O2. The article was titled 《Base-Promoted Cycloisomerization for the Synthesis of Indolizines and Related Heterocycles》. The information in the text is summarized as follows:

The base-mediated 5-exo-dig type cyclization reaction of homopropargyl pyridines for the construction of indolizines I (R1= COOEt, CN, COMe, etc.; R2 = Me, CH2C6H4, 4-ClC6H4CH2, 4-MeOC6H4CH2; R3 = H, 7-Me) has been reported for the first time. A variety of indolizine derivatives could be obtained in moderate to excellent isolated yields by treatment of homopropargyl pryidines with cesium carbonate in DMSO at 100°. This strategy could also be adapted to the synthesis of pyrrolo[1,2-a]quinolines and pyrrolo[1,2-a]pyrimidines from the corresponding homopropargyl quinolines and homopropargyl pyrimidines, resp. The mechanism involves α C-H deprotonation, 5-exo-dig cyclization, and isomerization of the exocyclic double bond to provide the heteroaromatic system. The transformation reported herein does not require the aid of transition metal catalysts or halogens, and is thus environmentally friendly. In the part of experimental materials, we found many familiar compounds, such as Ethyl 2-(pyrimidin-2-yl)acetate(cas: 63155-11-3Formula: C8H10N2O2)

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Li, Hongxian’s team published research in Organic Letters in 2017 | CAS: 63155-11-3

《Synthesis of Indolizines via Reaction of 2-Substituted Azaarenes with Enals by an Amine-NHC Relay Catalysis》 was written by Li, Hongxian; Li, Xiangmin; Yu, Yang; Li, Jianjun; Liu, Yuan; Li, Hao; Wang, Wei. Recommanded Product: 63155-11-3 And the article was included in Organic Letters on April 21 ,2017. The article conveys some information:

A metal-free catalytic strategy for the facile synthesis of biol. relevant mol. architectures indolizines and imidazopyridines was developed. The process is promoted by amine and N-heterocyclic carbene (NHC) relay catalysis via Michael addition-[3 + 2] fusion of simple azaarenes and α,β-unsaturated aldehydes. The preparative power is demonstrated in the synthesis of anxiolytic drug saripidem via two simple 1-pot operations with overall 45% yield. The experimental process involved the reaction of Ethyl 2-(pyrimidin-2-yl)acetate(cas: 63155-11-3Recommanded Product: 63155-11-3)

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Liu, Yuan’s team published research in Organic Chemistry Frontiers in 2017 | CAS: 63155-11-3

In 2017,Organic Chemistry Frontiers included an article by Liu, Yuan; Yu, Yang; Fu, Yiwei; Liu, Yonghai; Shi, Lei; Li, Hao; Wang, Wei. Computed Properties of C8H10N2O2. The article was titled 《Transition-metal-free synthesis of indolizines via [3 + 2]-annulation from α-bromoenals and 2-substituted azaarenes》. The information in the text is summarized as follows:

A transition-metal-free synthetic approach to synthesize indolizines from α-bromo-substituted enals and simple 2-substituted azaarenes were developed. A variety of functional groups were tolerated under mild reaction conditions. Moreover, Michael addition, intramol. N-alkylation and aromatization were involved in this convergent and feasible “”one-pot”” tandem reaction to afford the annulation products in moderate to good yields. In the part of experimental materials, we found many familiar compounds, such as Ethyl 2-(pyrimidin-2-yl)acetate(cas: 63155-11-3Computed Properties of C8H10N2O2)

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Brown, Desmond J.’s team published research in Australian Journal of Chemistry in 1977 | CAS: 63155-11-3

《Simple pyrimidines. XVI. A synthetic route to some 2-(pyrimidin-2′-yl)acetic acids and esters》 was published in Australian Journal of Chemistry in 1977. These research results belong to Brown, Desmond J.; Waring, Paul. Electric Literature of C8H10N2O2 The article mentions the following:

The pyrimidinylacetic acid derivatives I [R = CO2H, CONH2, C(:NH)OMe, CO2Et, C(:NH)OEt, CN, CO2Me; R1 = H, HO, Cl, MeO, Ph, Me; R2 = H, OH, Cl] were prepared Thus, H2NCOCH2C(:NH)NH2 was treated with PhCOCH2Et to give I (R = CONH2, R1 = Ph, R2 = OH) which with POCl3 gave I (R = CN, R1 = Ph, R2 = Cl). The nitrile was converted into the corresponding imidic ester and then into the carboxylic ester, which underwent dehalogenation to I (R = CO2Me, R1 = Ph, R2 = H) and subsequent hydrolysis to I (R = CO2H, R1 = Ph, R2 = H). After reading the article, we found that the author used Ethyl 2-(pyrimidin-2-yl)acetate(cas: 63155-11-3Electric Literature of C8H10N2O2)

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Schafer, Gabriel’s team published research in Organic Process Research & Development in 2020 | CAS: 63155-11-3

Category: pyrimidinesOn September 18, 2020 ,《Development of a Scalable Route for a Highly Polar Heterocyclic Aminocyclopropyl Building Block》 was published in Organic Process Research & Development. The article was written by Schafer, Gabriel; Ahmetovic, Muhamed; Fleischer, Tony; Abele, Stefan. The article contains the following contents:

A robust and scalable route toward key heterocyclic building block 1-(pyrimidin-2-yl)cyclopropan-1-amine hydrochloride from cyclopropanated starting material 1-amino-1-cyclopropanecarbonitrile hydrochloride was successfully developed. The key to success was the construction of a pyrimidine ring via cyclization from an amidine intermediate and a bench-stable 2-chloro vinamidinium hexafluorophosphate salt. The cyclization was performed under mild conditions, and the resulting 4-chloropyrimidine derivative was isolated in high yield and purity. The final hydrogenation was intensively optimized: A combination of Pd(OH)2/C as a catalyst and NaOMe as a base at 1 bar H2 pressure in MeOH simultaneously cleaved the Cbz group and dechlorinated the pyrimidine ring while at the same time suppressing the over-reduction of the pyrimidine ring to below 1.0%. After acidification with HCl, followed by removal of the catalyst and NaCl by filtration, the final product was isolated in high yield and purity as a bench-stable off-white solid. The overall yield of the five-step sequence was 57%. In the part of experimental materials, we found many familiar compounds, such as Ethyl 2-(pyrimidin-2-yl)acetate(cas: 63155-11-3Category: pyrimidines)

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Maruyama, Tatsuya’s team published research in European Journal of Medicinal Chemistry in 2009 | CAS: 63155-11-3

Maruyama, Tatsuya; Onda, Kenichi; Hayakawa, Masahiko; Matsui, Tetsuo; Takasu, Toshiyuki; Ohta, Mitsuaki published an article in European Journal of Medicinal Chemistry. The title of the article was 《Discovery of novel acetanilide derivatives as potent and selective β3-adrenergic receptor agonists》.Recommanded Product: 63155-11-3 The author mentioned the following in the article:

In the search for potent and selective human β3-adrenergic receptor (AR) agonists as potential drugs for the treatment of obesity and noninsulin-dependent (type II) diabetes, a novel series of acetanilide-based analogs were prepared and their biol. activities were evaluated at the human β3-, β2-, and β1-ARs. Among these compounds, 2-pyridylacetanilide, pyrimidin-2-ylacetanilide, and pyrazin-2-ylacetanilide derivatives exhibited potent agonistic activity at the β3-AR with functional selectivity over the β1- and β2-ARs. In particular, pyrimidin-2-ylacetanilide was found to be the most potent and selective β3-AR agonist with an EC50 value of 0.11 μM and no agonistic activity for either the β1- or β2-AR. In addition, these three compounds showed significant hypoglycemic activity in a rodent diabetic model. In the part of experimental materials, we found many familiar compounds, such as Ethyl 2-(pyrimidin-2-yl)acetate(cas: 63155-11-3Recommanded Product: 63155-11-3)

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Rani, Vangavaragu Jhansi’s team published research in Archiv der Pharmazie (Weinheim, Germany) in 2012 | CAS: 63155-11-3

The author of 《Synthesis and Spectral Characterization of New Bis(2-(pyrimidin-2-yl)ethoxy)alkanes and Their Pharmacological Activity》 were Rani, Vangavaragu Jhansi; Aminedi, Raghavendra; Polireddy, Kishore; Jagadeeswarareddy, Kanala. And the article was published in Archiv der Pharmazie (Weinheim, Germany) in 2012. Name: Ethyl 2-(pyrimidin-2-yl)acetate The author mentioned the following in the article:

The pyrimidine nucleus is an important component of nucleic acids (DNA and RNA) and vitamins (B2 and folic acid). It is evident from the literature that pyrimidine derivatives possess a wide spectrum of biol. activities such as antioxidant, anticancer, antibacterial, and anti-inflammatory activities. On the basis of diverse biol. activities, the authors attempted to synthesize a series of novel bis(2-(pyrimidin-2-yl)ethoxy)alkanes 5a-j in four steps with good yields. 2-Chloropyrimidine (1) was reacted with di-Et malonate in the presence of sodium hydride in dry DMF to yield the intermediate di-Et 2-(pyrimidin-2-yl)malonate (2), which on further reaction with sodium chloride and DMSO yielded Et 2-(pyrimidin-2-yl)ethanoate (3). Reduction with sodium borohydride (NaBH4) resulted in the formation of 2-(pyrimidin-2-yl)ethanol (4). This was further reacted with various dibromoalkanes to obtain the title compounds 5a-j. Next, the authors evaluated the antioxidant properties of the title compounds using four in vitro test systems: the 2,2-diphenyl-2-picrylhydrazyl radical-, superoxide radical-, and hydroxyl radical-scavenging assays, and the anti-lipid peroxidation activity test. The title compounds showed promising antioxidant activity when compared to butylated hydroxytoluene. The potency of their antioxidant activity was mainly influenced by the alkyl fragment attached to 2-(pyrimidin-2-yl)ethanol. The Et and Bu fragments linked to oxygen led to increased antioxidant activity of the title compounds (i.e., 5b and 5d) in all the in vitro assays. The results came from multiple reactions, including the reaction of Ethyl 2-(pyrimidin-2-yl)acetate(cas: 63155-11-3Name: Ethyl 2-(pyrimidin-2-yl)acetate)

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Ranganathan, Subramania’s team published research in Proceedings – Indian Academy of Sciences, Chemical Sciences in 1994 | CAS: 63155-11-3

Synthetic Route of C8H10N2O2On October 31, 1994 ,《The crafting of uracils with enhanced stacking potential》 appeared in Proceedings – Indian Academy of Sciences, Chemical Sciences. The author of the article were Ranganathan, Subramania; Kundu, Dinabandhu; Mehrotra, Sanjiv. The article conveys some information:

Uracils having enhanced stacking profile are of interest from diverse vantages ranging from the chem. simulation of transcription to the design of novel antiviral agents. This objective has been realized by synthetic strategies leading to uracils having, inter alia, pseudo aromatic and hydrophobic rings crafted to the 5-6 location and ionophore and hydrophobic chains affixed at the C-5 and nitrogen atoms. Endeavors to prepare a 5-2′ uracil-pyrimidine composite have led to novel uracil arising from 2-O → =CH(COOR)2 transformation and a tethered malonic acid pyrimidine complex. The results came from multiple reactions, including the reaction of Ethyl 2-(pyrimidin-2-yl)acetate(cas: 63155-11-3Synthetic Route of C8H10N2O2)

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Sources of common compounds: 63155-11-3

The synthetic route of 63155-11-3 has been constantly updated, and we look forward to future research findings.

Adding a certain compound to certain chemical reactions, such as: 63155-11-3, Ethyl 2-(pyrimidin-2-yl)acetate, 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: Ethyl 2-(pyrimidin-2-yl)acetate, blongs to pyrimidines compound. name: Ethyl 2-(pyrimidin-2-yl)acetate

To a solution of ethyl 2-(pyrimidin-2-yl)acetate (Example 31b, 410 mg, 2.47 mmol)in ethanol (5 mL) was added 2N NaOH (2 mL) at room temperature under nitrogen. Thereaction mixture was stirred at room temperature under nitrogen for 72 hours, then5 concentrated under reduced pressure. The residue was triturated with ethanol andconcentrated under reduced pressure to give the title compound, which was carried onto thenext step without further purification. MS 139 (MH+).

The synthetic route of 63155-11-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SENOMYX, INC.; TACHDJIAN, Catherine; KARANEWSKY, Donald; WERNER, Sara; DARMOHUSODO, Vincent; YAMAMOTO, Jeff; WO2014/25706; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The origin of a common compound about Ethyl 2-(pyrimidin-2-yl)acetate

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,63155-11-3, its application will become more common.

Electric Literature of 63155-11-3 ,Some common heterocyclic compound, 63155-11-3, molecular formula is C8H10N2O2, 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.

To a mixture of ethyl 2-pyrimidin-2-ylacetate (900 mg, 5.42 mmol) in THF (20 mL) was added LDA (3.25 mL, 6.5 mmol) at -78 C, then the mixture was stirred at -78 C for 2 hours. To the mixture was added iodomethane (922.46 mg, 6.5 mmol), then the mixture was stirred at -78 C to 20 C for 3 hours. The mixture was quenched with sat. NH4C1 (30 mL), then the mixture was extracted with EtOAc (50 mL x 2). The combined organic phase was washed with water (20 mL) and brine (20 mL), dried over Na2S04, filtered and concentrated to give the crude product. The crude product was purified by flash chromatography on silica gel (EtOAc in PE = 0% to 20% to 45%) to give the product (730 mg, 4.05 mmol, 75% yield) as oil. 1H NMR (CDC13, 400MHz) deltaH = 8.72 (d, 2H), 7.19 (t, 1H), 4.19 (q, 2H), 4.14 – 4.07 (m, 1H), 1.62 (d, 3H), 1.22 (t, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,63155-11-3, its application will become more common.

Reference:
Patent; PRAXIS PRECISION MEDICINES , INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (244 pag.)WO2018/148745; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia