Category: 29274-24-6

Adding a certain compound to certain chemical reactions, such as: 29274-24-6, 5-Chloropyrazolo[1,5-a]pyrimidine, 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: 5-Chloropyrazolo[1,5-a]pyrimidine, blongs to pyrimidines compound. name: 5-Chloropyrazolo[1,5-a]pyrimidine

5-Chloropyrazolo[1,5-a]pyrimidine (1 g, 6.51 mmol) was dissolvedin anhydrous DMF (10 mL) and cooled to 5 C. Phosphorousoxychloride (1.82 mL, 19.5 mmol) was added and thereaction was allowed to warm slowly to RT and stirred for 16 h.The reaction was poured onto ice (200 g) and the pH wasadjusted to pH 10 with 1 M NaOH. The aqueous suspension wasextracted with CH2CL2 (100 mL) and the aqueous layer was washedwith CH2Cl2 (2 50 mL). The combined organic layers werewashed with water (2 70 mL), brine (50 mL), dried (WhatmanPS1 filter paper) and the solvent was removed in vacuo. The crudeproduct was adsorbed onto silica and purified by automated flashchromatography on silica gel (0-50% EtOAc-cyclohexane) to yieldthe title compound (8) (864 mg, 73%) as a colourless solid. 1H NMRdH (d6-DMSO, 300 MHz), 10.09 (s, 1H), 9.39 (d, J 7.2, 1H), 8.77 (s,1H), 7.49 (d, J 7.2, 1H); LC-MS tR 4.08 min; LC254 99.0%; m/z182.2/184.1 [M+H].

The synthetic route of 29274-24-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Phillipson, Louisa J.; Segal, David H.; Nero, Tracy L.; Parker, Michael W.; Wan, Soo San; De Silva, Melanie; Guthridge, Mark A.; Wei, Andrew H.; Burns, Christopher J.; Bioorganic and Medicinal Chemistry; vol. 23; 19; (2015); p. 6280 – 6296;,
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. 29274-24-6, name is 5-Chloropyrazolo[1,5-a]pyrimidine. A new synthetic method of this compound is introduced below., Computed Properties of C6H4ClN3

Preparation 1; The solution of 5-chloropyrazolo [ 1, 5-a] pyrimidine (200 mg) and trans-4-methoxycyclohexanamine (168 mg) in isopropylalcohol(2 ml) was refluxed for 3 hours. After cooling to ambient temperature, the reaction mixture was poured into water, then extracted with ethyl acetate . The organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel EPO elupsilonting with chloroform/methanol ( 100 : 0 to 100:10) to give N- (trans-4-methoxycyclohexyl)pyrazolo [1, 5-a] pyrimidin-5- amine (70 mg) .1H-NMR (DMSO-d6) 5:1.13-1.34 (4H,m) ,1-91-2.08 (4H,m) , 3.09-3.20 ( IH, m) ,3.33 (3H,s) , 3.70-3.86 (lH,m) ,5.95 (IH, d, J=2. OHz) ,6.19 (IH , d, J=7.6Hz) , 7.26(lH,d, J=7.4Hz) ,7.74 ( IH, d, J=2. OHz) , 8.41 (IH, d , J=7.6 Hz) . MS:247 (MH-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, 29274-24-6, 5-Chloropyrazolo[1,5-a]pyrimidine.

Reference:
Patent; ASTELLAS PHARMA INC.; WO2007/13673; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 29274-24-6, 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. 29274-24-6, name is 5-Chloropyrazolo[1,5-a]pyrimidine. A new synthetic method of this compound is introduced below.

5-Aryl/heteroaryl-ethynyl-pyrazolo[1 ,5-a]pyrimidines (51 )[00143] Under a strong stream of argon, aryltrimethylsilylacetylene, 5-chloro- pyrazolo[1 ,5-a]pyrimidine (1 equivalent), PdCI2(PPh3J2 (5 mol %) and copper (I) iodide (5 mol %) are placed in a vial containing DMF. The mixture is flushed thoroughly with argon and Et3N (4 equivalents) is added through the septum. The reaction mixture is warmed to 60 0C and TBAF (1.1 equivalent) in DMF is added dropwise. The mixture is stirred at 60 0C for 3h, the solvent is evaporated and the residue is purified by flash column chromatography to give the desired product. Yields 20-60%.; Example 1 3-Pyrazolo[1,5-a]pyrimidin-5-ylethynyl-benzonitrile[00177] According to General Procedure 1 , 3-[(trimethylsilyl)ethynyl]benzonitrile is reacted with 5-chloro-pyrazolo[1 ,5-a]pyrimidine to provide the title compound in good yield.1H NMR (CDCI3, TMS) delta: 6.76, 6.98, 7.53, 7.72, 7.88, 8.19, 8.69.LC/MS: (M+H)= 245

At the same time, in my other blogs, there are other synthetic methods of this type of compound,29274-24-6, 5-Chloropyrazolo[1,5-a]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; MERZ PHARMA GMBH & CO. KGaA; HENRICH, Markus; WEIL, Tanja; NAGEL, Jens; GRAVIUS, Andreas; MUeLLER, Sibylle; KAUSS, Valerjans; ZEMRIBO, Ronalds; FOTINS, Juris; WO2010/63487; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 29274-24-6, 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. 29274-24-6, name is 5-Chloropyrazolo[1,5-a]pyrimidine. A new synthetic method of this compound is introduced below.

5-Aryl/heteroaryl-ethynyl-pyrazolo[1 ,5-a]pyrimidines (51 )[00143] Under a strong stream of argon, aryltrimethylsilylacetylene, 5-chloro- pyrazolo[1 ,5-a]pyrimidine (1 equivalent), PdCI2(PPh3J2 (5 mol %) and copper (I) iodide (5 mol %) are placed in a vial containing DMF. The mixture is flushed thoroughly with argon and Et3N (4 equivalents) is added through the septum. The reaction mixture is warmed to 60 0C and TBAF (1.1 equivalent) in DMF is added dropwise. The mixture is stirred at 60 0C for 3h, the solvent is evaporated and the residue is purified by flash column chromatography to give the desired product. Yields 20-60%.; Example 1 3-Pyrazolo[1,5-a]pyrimidin-5-ylethynyl-benzonitrile[00177] According to General Procedure 1 , 3-[(trimethylsilyl)ethynyl]benzonitrile is reacted with 5-chloro-pyrazolo[1 ,5-a]pyrimidine to provide the title compound in good yield.1H NMR (CDCI3, TMS) delta: 6.76, 6.98, 7.53, 7.72, 7.88, 8.19, 8.69.LC/MS: (M+H)= 245

At the same time, in my other blogs, there are other synthetic methods of this type of compound,29274-24-6, 5-Chloropyrazolo[1,5-a]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; MERZ PHARMA GMBH & CO. KGaA; HENRICH, Markus; WEIL, Tanja; NAGEL, Jens; GRAVIUS, Andreas; MUeLLER, Sibylle; KAUSS, Valerjans; ZEMRIBO, Ronalds; FOTINS, Juris; WO2010/63487; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 29274-24-6 , The common heterocyclic compound, 29274-24-6, name is 5-Chloropyrazolo[1,5-a]pyrimidine, molecular formula is C6H4ClN3, 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 solution of 5-chloropyrazolo[1,5-a]pyrimidine (200 mg, 1.30 mmol) in DMF (2 mL) was added N-iodosuccinimide (322 mg, 1.86 mmol). The reaction was stirred at rt overnight, then diluted with EtOAc (100 mL), and washed with H2O (50 mL), saturated Na2S2O3 aqueous solution (50 mL) and brine (50 mL). The separated organic phase was dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtOAc/PE (v/v)=1/4) to give the title compound as a pale yellow solid (390 mg, 100%). [0309] MS (ESI, pos. ion) m/z: 279.9 [M+H]+. [0310] 1H NMR (400 MHz, CDCl3) delta (ppm): 8.57 (d, J=7.2 Hz, 1H), 8.16 (s, 1H), 6.86 (d, J=7.2 Hz, 1H)

The synthetic route of 29274-24-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; Xi, Ning; US2014/234254; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 29274-24-6 ,Some common heterocyclic compound, 29274-24-6, molecular formula is C6H4ClN3, 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 32-Methyl-4-pyrazolo[1 ,5-a]pyrimidin-5-yl-but-3-yn-2-ol (5a); [00151] Compound 1a, 2-methyl-but-3-yn-2-ol (1.5 equivalents), Pd CI2[PPh3]2 (5 mol %) and CuI (10 mol %) in diethyl amine is refluxed under argon for 2 h (TLC control), then cooled and evaporated to dryness. The residue is dissolved in dichloromethane; the target product is isolated by column chromatography (silica gel, ethyl acetate – hexane, 1 :2). The solvent is evaporated under reduced pressure; the residue is crystallized from diethyl ether to give the title compound in good yield.1H NMR (DMSO-d6, 400 MHz) delta (ppm), 1.51 (s, 6H), 6.69 (s, 1 H), 6.98 (d, 1 H), 8.22 (s.1 H)1 9.06 (d, 1 H). m/z (APCI+) 202 (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,29274-24-6, its application will become more common.

Reference:
Patent; MERZ PHARMA GMBH & CO. KGaA; HENRICH, Markus; WEIL, Tanja; NAGEL, Jens; GRAVIUS, Andreas; MUeLLER, Sibylle; KAUSS, Valerjans; ZEMRIBO, Ronalds; FOTINS, Juris; WO2010/63487; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 29274-24-6, name is 5-Chloropyrazolo[1,5-a]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H4ClN3

To benzyl (7S)-7-methyl-5-(2-(2H-1,2,3-triazol-2-yl)benzoyl)-1,2,5-oxadiazepane-2-carboxylate (4.4 g) obtained in Step A of Example 2 was added 5.1M hydrogen bromide acetic acid solution (30 mL), and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated under reduced pressure, to a solution of the residue in 2-propanol (40 mL) was added 4-chloro-2,6-dimethylpyrimidine (2.23 g), and the mixture was stirred at 70 C. for 10 hr. The reaction mixture was cooled to 0 C., saturated aqueous sodium hydrogencarbonate solution was added thereto, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate), and crystallized (heptane/ethyl acetate) to give the title compound (2.30 g). 1H NMR (300 MHz, DMSO-d6) delta 1.02-1.50 (3H, m), 2.16-2.46 (6H, m), 2.95-3.29 (1H, m), 3.40-3.75 (3H, m), 3.79-4.74 (3H, m), 6.31-6.77 (1H, m), 7.05-8.30 (6H, m). MS: [M+H]+ 394.1. d value (or d-spacing) of specific peak in powder X-ray diffraction pattern=15.5, 7.9, 7.7, 7.4, 6.5, 5.6, 5.1, 4.3, 4.0, 3.67, 3.62, 3.57, 3.52 A. The title compound (11.4 mg) was obtained using ((7S)-7-methyl-1 ,2,5-oxadiazepan-5-yl)(2-(2H- 1 ,2,3-tri- azol-2-yl)phenyl)methanone hydrobromide (60 mg) obtained in Step A of Example 92 and 5-chloropyrazolo[1, 5-a]pyrimidine (26.1 mg) obtained in Reference Example 24 in the same manner as in Step B of Example 2. MS: [M+H]+405.1.

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, 29274-24-6, 5-Chloropyrazolo[1,5-a]pyrimidine.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KAMEI, Taku; ARIKAWA, Yasuyoshi; OHASHI, Tomohiro; IMAEDA, Toshihiro; FUJIMORI, Ikuo; MIKI, Takashi; YONEMORI, Jinichi; OGURO, Yuya; SUGIMOTO, Takahiro; SETO, Masaki; NISHIDA, Goushi; KAMATA, Makoto; IMOTO, Hiroshi; (132 pag.)US2018/155333; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 29274-24-6, 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. 29274-24-6, name is 5-Chloropyrazolo[1,5-a]pyrimidine, molecular formula is C6H4ClN3, 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.

The residue B-2 prepared in the above Example 7 was added to 9 mL of 1:1 sulfuric acid nitric acid at 0 C. Controlling the reaction temperature did not exceed 5, reaction time 2h, after the reaction is completed, carefully add water. The product was filtered off, and the product was crystallized from ethyl acetate to give the product 5.1 g, yield 86%. HPLC purity ? 99%.

According to the analysis of related databases, 29274-24-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhejiang Normal University; Li Xinsheng; Chen Xiuhua; Chen Xueke; Luo Hongmin; (13 pag.)CN109354578; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 29274-24-6 ,Some common heterocyclic compound, 29274-24-6, molecular formula is C6H4ClN3, 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.

[0211] Step 3. Pyrazolo[1,5-alpyrimidine-5-carboxylic acid methyl ester. A mixture of 5- chloro-pyrazolo[1,5-a]pyrimidine (2 g, 13.02 mmol, 1.00 equiv), triethylamine (4 mL), methanol (80 mL), and bis(triphenylphosphine)palladium(II) dichloride (1 g, 1.42 mmol, 0.11 equiv) was stirred in a 100-mL pressure reactor overnight at 100 C under 10 atmospheres of carbon monoxide. The reaction mixture was cooled to rt then concentrated under vacuum.The residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1:5) to yield 1.2 g (52%) of the title compound as a light yellow solid. LC/MS (Method I, ESI): RT= 1.09 mi m/z = 178.0 [M+Hf?.

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. 29274-24-6, 5-Chloropyrazolo[1,5-a]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GENENTECH, INC.; FORMA TM, LLC; BAIR, Kenneth, W.; BAUMEISTER, Timm, R.; GOSSELIN, Francis; ZAK, Mark; ZHENG, Xiaozhang; WO2013/130935; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 29274-24-6, 5-Chloropyrazolo[1,5-a]pyrimidine, 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, 29274-24-6, blongs to pyrimidines compound. Application In Synthesis of 5-Chloropyrazolo[1,5-a]pyrimidine

5-Chloropyrazolo[l,5-a]pyri midine (500mg, 3.25mmol) taken up in 3ml acetonitrile and 1.5ml water. 2-isopropoxy-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine (lg, 3.9m mol), Potassiu m carbonate (902mg, 6.5m mol), and Pd(dppf)Cl2:DCM (267mg, 0.325m mol) added and reaction stirred in microwave in a sealed tube at 120 C for 12 minutes. Reaction cooled filtered through celite washed through with ethyl acetate and reduced in vacuo. Reaction taken up in 1:1 ethyl acetate: hexane and filtered through a plug of celite. The filtrate was ollected, dried in vacuo to obtain 740 mg of crude product to be used as is in next step. LRMS (ESI) m/z 255 [(M+H)]+, calc’d for C14H14N4O: 254.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,29274-24-6, its application will become more common.

Reference:
Patent; LEXICON PHARMACEUTICALS, INC.; BI, Yingzhi; GARDYAN, Michael Walter; GREEN, Michael Green; KUMI, Godwin; ZHANG, Yulian; WO2015/35117; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia