Category: 1224944-77-7

Application of 1224944-77-7, 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.1224944-77-7, name is Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate, molecular formula is C9H8ClN3O2, molecular weight is 225.63, as common compound, the synthetic route is as follows.

Chiral amine ((S) -2- (2-((R) -1-aminoethyl) -4-fluorophenoxy) propyl-3,3,3-d3) carbamic acid tert-butyl ester (10g ) And 5-chloropyrazolo [1,5-a] pyrimidine-3-carboxylic acid ethyl ester (10g)Diisopropylethylamine base (6.5g) in n-butanol solvent (50mL)The target compound was obtained by condensation at 114-120 C for 8 hours.

Statistics shows that 1224944-77-7 is playing an increasingly important role. we look forward to future research findings about Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate.

Reference:
Patent; Jiao Yuqi; (29 pag.)CN110577549; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1224944-77-7 ,Some common heterocyclic compound, 1224944-77-7, molecular formula is C9H8ClN3O2, 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 ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate (677 mg, 3.00 mmol), Nmethylmethanamine hydrochloride (489 mg, 6.00 mmol) and N,N-diisopropylethylamine (1 .6 ml, 9.0 mmol) in 2-propanol (20 ml) was refluxed for 5 h. Upon cooling, ice water was added and the mixture was extracted with ethyl acetate (3x). The combined organic phases were filtrated through a silicone filter and concentrated to give the title compound (674 mg).[C-MS (Method 1): R = 0.84 mm; MS (ESIpos): m/z = 235 [M+H]1H-NMR (400 MHz, DMSO-d6) 6 [ppm]: 1.261 (7.26), 1.278 (16.00), 1.296 (7.57), 3.182(14.34), 4.157 (2.25), 4.175 (7.19), 4.193 (7.07), 4.211 (2.14), 6.691 (4.60), 6.710 (4.61),8.181 (9.13), 8.673 (5.48), 8.693 (5.36).

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. 1224944-77-7, Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERMANN, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; HOLTON, Simon; BENDER, Eckhard; LI, Volkhart; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; BAIRLEIN, Michaela; VON NUSSBAUM, Franz; HERBERT,Simon; KOPPITZ, Marcus; (734 pag.)WO2016/177658; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1224944-77-7, 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 1224944-77-7 as follows.

Chiral amine ((S) -2- (2-((R) -1-aminoethyl) -4-fluorophenoxy) propyl-3,3,3-d3)Tert-butyl carbamate (10g) and 5-chloropyrazolo [1,5-a] pyrimidine-3-carboxylic acid ethyl ester (10g)Diisopropylethylamine base (6.5g) in n-butanol solvent (50mL)The target compound was obtained by condensation at 114-120 C for 8 hours.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1224944-77-7, its application will become more common.

Reference:
Patent; Jiao Yuqi; (29 pag.)CN110577549; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 1224944-77-7, Adding some certain compound to certain chemical reactions, such as: 1224944-77-7, name is Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate,molecular formula is C9H8ClN3O2, 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 1224944-77-7.

Nitrogen was bubbled through a solution of ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate (5.40 g, 23.94 mmol) in dioxane/ EtOH/H2O (130 mL, 20:3:3). 2-(trifluoromethyl)phenylboronic acid (6.80 g, 35.90 mmol), Pd(PPh3)4 (2.80 g, 2.39 mmol), and Cs2CO3 (15.60 g, 47.88 mmol) were added and the reaction mixture was heated at reflux for 2 h. The mixture was cooled to room temp, poured into EtOAc (300 mL) washed with brine, dried (MgSO4), and concentrated. The crude residue was purified by MPLC eluting with pentane/EtOAc (0-100%) to give ethyl 5-(2-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (6.30 g, 78 % yield). MS (ESI) calcd for C16H12F3N3O2 (m/z): 335.09; found: 336 [M+H].

According to the analysis of related databases, 1224944-77-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GlaxoSmithKline LLC; CASAUBON, Rebecca, L.; NARAYAN, Radha; OALMANN, Christopher; VU, Chi, B.; (583 pag.)EP2768509; (2017); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1224944-77-7, 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 1224944-77-7 as follows.

A mixture of ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate (1.00 g, 4.43 mmol), 2-(2,5-difluorophenyl)pyrrolidine (Intermediate 2, 853 mg, 4.65 mmol) and KF (1.28 g, 22.1 mmol) in DMSO (14 mL) was stirred at 180 C. for 2 hours. After being cooled to room temperature, the reaction mixture was poured into water. The mixture was stirred for 30 min. A precipitated solid was collected by filtration and dried under vacuum to afford ethyl 5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (1.51 g, 91%) as a yellow solid. 1H-NMR (CDCl3, Varian, 400 MHz): delta 1.30-1.49 (3H, m), 1.98-2.18 (3H, m), 2.43-2.58 (1H, m), 3.95-4.20 (2H, m), 4.25-4.48 (2H, m), 5.18-5.23 (1H, m), 5.82-5.94 (1H, m), 6.68-6.80 (1H, m), 6.86-6.98 (1H, m), 7.00-7.12 (1H, m), 8.08-8.22 (1H, m), 8.29 (1H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1224944-77-7, its application will become more common.

Reference:
Patent; HANDOK INC.; CMG Pharmaceutical Co., Ltd.; Kim, Moonsoo; Lee, Chaewoon; Lee, Gilnam; Yoon, Cheolhwan; Seo, Jeongbeob; Kim, Jay Hak; Lee, Minwoo; Jeong, Hankyul; Choi, Hyang; Jung, Myung Eun; Lee, Ki Nam; Kim, Hyun Jung; Kim, Hye Kyoung; Lee, Jae Il; Lee, MinWoo; Kim, Misoon; Choi, Soongyu; (124 pag.)US2016/168156; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1224944-77-7 ,Some common heterocyclic compound, 1224944-77-7, molecular formula is C9H8ClN3O2, 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.

ompound 4 (2 g, 10.5 mmol) and Compound 7 (2.4 g, 10.5 mmol)Add to n-butanol (50 mL) in turn, then add diisopropylethylamine (10.8 g, 84 mmol).The temperature was raised to 120 C and stirred overnight, and TLC showed that the starting material disappeared.N-butanol is removed under reduced pressure,Water (50 mL) was added to the residue.Extracted with ethyl acetate (50 mL*3).The organic phases were combined and dried over anhydrous magnesium sulfate.Filtration, concentration, silica gel column chromatography (PE: EA = 1:1)Obtained a white solid 8 (3.1 g),The generation rate is 97%.

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. 1224944-77-7, Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhengzhou Taijihongnuo Pharmaceutical Co., Ltd.; Wu Yusheng; Zhi Wubin; Li Jingya; Wang Xin; Wu Shiyong; Liang Apeng; Guo Ruiyun; (31 pag.)CN109516999; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 1224944-77-7, 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. 1224944-77-7, name is Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate. A new synthetic method of this compound is introduced below.

A mixture of ethyl 5-chloropyrazolo[1 ,5-a]pyrimidine-3-carboxylate (677 mg, 3.00 mmol), methanamine (3.0 ml, 2.0 M, 6.0 mmol) and N,N-diisopropylethylamine (1.6 ml, 9.0 mmol) in 2-propanol (20 ml) was refluxed for 5 h. Upon cooling, ice water was added and the mixturewas extracted with ethyl acetate (3x). The combined organic phases were filtrated through a silicone filter and concentrated to give the title compound (570 mg).[C-MS (Method 1): R = 0.74 mm; MS (ESIneg): m/z = 219 [M-H]1H-NMR (400 MHz, DMSO-d6) 6 [ppm]: 1.258 (7.44), 1.276 (16.00), 1.293 (7.62), 1.296 (2.96), 1.338 (1.13), 2.902 (6.89), 2.914 (6.83), 4.155 (3.10), 4.173 (9.99), 4.191 (9.82),4.209 (2.93), 6.336 (1.70), 6.355 (1.74), 7.855 (1.41), 7.867 (1.40), 8.126 (5.66), 8.482 (1.60), 8.501 (1.56).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1224944-77-7, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERMANN, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; HOLTON, Simon; BENDER, Eckhard; LI, Volkhart; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; BAIRLEIN, Michaela; VON NUSSBAUM, Franz; HERBERT,Simon; KOPPITZ, Marcus; (734 pag.)WO2016/177658; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1224944-77-7, Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate, 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, 1224944-77-7, blongs to pyrimidines compound. Quality Control of Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate

[0347] Step 4: To a solution of 5-Chloro-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester (100 mg, 0.44 mmol) and 11-iD (110 mg, 0.41 mmol) in anhydrous THF (5.0 mL) at – 78C, NaH (60%, 17 mg, 0.44 mmol) was added. The mixture was allowed to warm to rt and stilTed for 8 hours until a good amount of desired product was formed. The mixture was then diluted with water/ice and extracted with DCM (3×20 mL). The organic layer was dried over Na2SO4, concentrated and purified by silica gel column chromatography to afford 1 1-1E as a yellow liquid (20 mg, 0.045 mmol, 6%), which is used directly in the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1224944-77-7, its application will become more common.

Reference:
Patent; TP THERAPEUTICS, INC.; CUI, Jingrong Jean; LI, Yishan; ROGERS, Evan W.; ZHAI, Dayong; WO2015/112806; (2015); A3;,
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. 1224944-77-7, name is Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate. A new synthetic method of this compound is introduced below., Recommanded Product: 1224944-77-7

To a solution of (tf)-2-(l-aminoethyl)-4-fluorophenol (2) (85 g, 443.56 mmol, 1.00 eq.) and ethyl 5-chloropyrazolo[l,5-a]pyrimidine-3-carboxylate (la) (100.08 g, 443.56 mmol, 1.00 eq.) in n-BuOH (2 L) was added DIEA (343.96 g, 2.66 mol, 6.00 eq.). The mixture was stirred at 120 C for 2 hrs. TLC (PE:EtOAc=l : l) showed the reaction was completed. The reaction mixture was diluted with H20 (500 mL) at 16 C, and extracted with EtOAc (500 mLx3). The combined organic layers were washed with brine (500 mL), dried over Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (Si02, Petroleum ether/Ethyl acetate=10/l to 1 :3) to give ethyl (K)-5-((l-(5- fluoro-2-hydroxyphenyl)ethyl)amino)pyrazolo[l,5-a]pyrimidine-3-carboxylate (3) (122 g, 349.34 mmol, 78.76% yield, ee>99% purity) as a white solid. 1HNMR (CDC13 , 400MHz) delta 9.28 (br. s., IH), 8.26 (s, IH), 8.14 (d, 7=7.5 Hz, IH), 6.95 – 6.89 (m, 2H), 6.87 – 6.80 (m, IH), 6.18 (d, 7=7.5 Hz, IH), 5.98 (d, 7=8.3 Hz, IH), 5.71 – 5.54 (m, IH), 4.50 – 4.35 (m, 2H), 1.60 (d, 7=6.8 Hz, 3H), 1.42 (t, J=7.2 Hz, 3H).

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, 1224944-77-7, Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate.

Reference:
Patent; TP THERAPEUTICS, INC.; CUI, Jingrong Jean; LI, Yishan; ROGERS, Evan W.; ZHAI, Dayong; DENG, Wei; HUANG, Zhongdong; (120 pag.)WO2017/15367; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1224944-77-7, 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.1224944-77-7, name is Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate, molecular formula is C9H8ClN3O2, molecular weight is 225.63, as common compound, the synthetic route is as follows.

Nitrogen was bubbled through a solution of ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate (5.40 g, 23.94 mmol) in dioxane/EtOH H2O (130 mL, 20:3:3). 2-(trifluoromethyl)phenylboronic acid (6.80 g, 35.90 mmol), Pd(PPh3)4 (2.80 g, 2.39 mmol), and Cs2CO3 (15.60 g, 47.88 mmol) were added and the reaction mixture was heated at reflux for 2 h. The mixture was cooled to room temp, poured into EtOAc (300 mL) washed with brine, dried (MgSO4), and concentrated. The crude residue was purified by MPLC eluting with pentane/EtOAc (0-100%) to give ethyl 5-(2-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (6.30 g, 78 % yield). MS (ESI) calcd for C16H12F3N3O2 (m/z): 335.09; found: 336 [M+H]

Statistics shows that 1224944-77-7 is playing an increasingly important role. we look forward to future research findings about Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; CASAUBON, Rebecca, L.; NARAYAN, Radha; OALMANN, Christopher; VU, Chi, B.; WO2013/59587; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia