Tag: M.W:100-200

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. 49844-90-8, name is 4-Chloro-2-(methylthio)pyrimidine, molecular formula is C5H5ClN2S, 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. Quality Control of 4-Chloro-2-(methylthio)pyrimidine

General procedure: alpha,beta-unsaturated tosylhydrazones 1 (0.11 mmol, 1.1 equiv), heteroaryl chlorides 2 (0.1 mmol, 1 equiv), Cs2CO3 (0.25 mmol, 2.5 equiv) and MeCN (1 mL) were added to a tube. The mixture was stirred at 60 C until the heteroaryl chlorides was completely disappeared for 4-8h. After cooling to room temperature, the mixture was quenched with NH4Cl (2 mL, saturated aqueous solution) and extracted with CH2Cl2 (3 × 2 mL). The combined organic phases were dried over Na2SO4 and solvents removed in vacuo. The residue was purified by flash column chromatography on silica gel with ethyl acetate/petroleum ether (1:10-1:4, V/V) as the eluent, affording the desired product 3 and 4.

With the rapid development of chemical substances, we look forward to future research findings about 49844-90-8.

Reference:
Article; Zeng, Lin; Guo, Xiao-Qiang; Yang, Zai-Jun; Gan, Ya; Chen, Lian-Mei; Kang, Tai-Ran; Tetrahedron Letters; vol. 60; 33; (2019);,
Pyrimidine | C4H4N2 – PubChem,
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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 582313-57-3, name is 4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 582313-57-3

To a solution of trans-4-(dimethylamino)cyclohexan-l-ol (280 mg, 1.95 mmol, 3.90 equiv) in tetrahydrofuran (5 mL) was added sodium hydride (200 mg, 5.00 mmol, 9.97 equiv, 60percent). The mixture was stirred at 0°C for 30 min. Then 4-chloro-5-fluoro-7H-pyrrolo[2,3- d]pyrimidine (86 mg, 0.50 mmol, 1.00 equiv) was added. The resulting solution was stirred for 16 h at 70°C. The resulting solution was extracted with 5×15 mL of dichloromethane and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product (70 mg) was purified by Prep-HPLC with the following conditions: Column, SunFire Prep CI 8, 19* 150mm 5um; mobile phase, Water with 50mmol NH4HCO3 and CH3CN (5.0percent CH3CN up to 25.0percent in 10 min, up to 95.0percent in 2 min,down to 5.0percent in 2 min); Detector, uv 254/220nm. This resulted in 31 mg (22percent) of trans-4-([5-fluoro-7H-pyrrolo[2,3- d]pyrimidin-4-yl]oxy)-N,N-dimethylcyclohexan-l -amine as a off-white solid. LC-MS: (ES,m/z): 279 [M+H] + 1H NMR (300 MHz, CD3OD, ppm): delta 1.64-1.38 (m, 4H), 1.99-2.07 (m, 2H), 2.25- 2.40 (m, 9H), 5.16-5.20 (m, 1H), 6.96 (d, 1H), 8.25 (s, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 582313-57-3.

Reference:
Patent; NIMBUS IRIS, INC.; HARRIMAN, Geraldine C.; ROMERO, Donna L.; MASSE, Craig E.; ROBINSON, Shaughnessy; WESSEL, Matthew David; GREENWOOD, Jeremy Robert; WO2014/11911; (2014); A2;,
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Synthetic Route of 63200-54-4, 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.63200-54-4, name is 2,4-Dichloro-5H-pyrrolo[3,2-d]pyrimidine, molecular formula is C6H3Cl2N3, molecular weight is 188.0141, as common compound, the synthetic route is as follows.

2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine (134 mg, 0.71 mmol), NaHCO3 (66 mg, 0.78 mmol) and Pd/C (1.52 mg, 10%) were mixed in EtOH (4 ml). Hydrogen (3 psi) was applied and the mixture was stirred for 2.5 hours at room temperature. The mixture was passed through a plug of celite and the filtrate was evaporated. The residue was purified by flash chromatography to afford 90 mg (88%) of the title compound. LC/MS (20-100% CH3CN:0.05% HCOOH(aq) gradient over 5 min): 1.58 min. 154 M+H.

The chemical industry reduces the impact on the environment during synthesis 63200-54-4, I believe this compound will play a more active role in future production and life.

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;,
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Electric Literature of 93366-88-2, 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.93366-88-2, name is 7H-Pyrrolo[2,3-d]pyrimidin-2-amine, molecular formula is C6H6N4, molecular weight is 134.14, as common compound, the synthetic route is as follows.

7H-pyrrolo[2,3-d]pyrimidin-2-amine (134 mg, 1.00 mmol), 2-bromo-5-fluoro-4-iodopyridine (604 mg, 2.00mmol),potassium carbonate (415 mg, 3.00 mmol) and proline (23 mg, 0.2 mmol) was added to the eggplant flask,dimethyl sulfoxide was added, and the reaction solution was deoxidized. Copper iodide (19 mg, 0.1 mmol) was added and the reaction solution was deoxygenated. Heat to 90 C and stir for 16 hours. After the reactionwas completed, it was cooled to room temperature, water and ethyl acetate were added, and the mixture was filtered over celite. The target compound was obtained in 246 mg.

Statistics shows that 93366-88-2 is playing an increasingly important role. we look forward to future research findings about 7H-Pyrrolo[2,3-d]pyrimidin-2-amine.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhao Yujun; Li Zhiqiang; Yan Ziqin; Li Jia; Zhou Yubo; Su Mingbo; Chen Zheng; (138 pag.)CN109810110; (2019); A;,
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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. 4318-56-3, name is 6-Chloro-3-methylpyrimidine-2,4(1H,3H)-dione. This compound has unique chemical properties. The synthetic route is as follows. Formula: C5H5ClN2O2

C. Preparation of 2-(6-chloro-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin- l-ylmethyl)-4-fluoro-benzonitrile (Compound D)E[0217] Compound E was prepared by stirring a mixture of crude 3-methyl-6- chlorouracil D (0.6 g, 3.8 mmol), 2-bromomethyl-4-fluorobenzonitrile (0.86 g, 4 mmol) and K2CO3 (0.5 g, 4 mmol) in DMSO (10 mL) at 60 C for 2 hours. The reaction was diluted with water and extracted with EtOAc. The organics were dried over MgSO4 and the solvent removed. The residue was purified by column chromatography. 0.66 g of the product was obtained (yield: 60%). 1H-NMR (400 MHz, CDCl3): delta 7.73 (dd, J=7.2, 8.4Hz, IH), 7.26 (d, J-4.0Hz, IH), 7.11-7.17 (m, IH), 6.94 (dd, J=2.0, 9.0 Hz, IH), 6.034 (s, 2H), 3.39 (s, 3H). MS (ES) [m+H] calc’d for Ci3H9ClFN3O2, 293.68; found 293.68.

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, 4318-56-3, 6-Chloro-3-methylpyrimidine-2,4(1H,3H)-dione.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2008/67465; (2008); A1;,
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Electric Literature of 211244-81-4, 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. 211244-81-4, name is 2-(Methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one, molecular formula is C8H7N3OS, 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 solution of 2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin- 7-one (120 mg, 0.62 mmol) in anhydrous dimethylformamide (2 mL), sodium hydride (60% in mineral oil, 37 mg, 0.93 mmol) was added and stirred at room temperature. After 30 min, a solution of 4-chloromethyl-5-cyclopropylthiazole (140 mg, 0.81 mmol) in anhydrousdimethylformamide (2 mL) was added slowly and the stirring was continued for 18 h. The resulting mixture was poured into ice water (20 g), and extracted with dichloromethane (3 x 20 mL). The combined organic layers were dried over sodium sulfate, filtered and evaporated. The residue was purified by column chromatography using dichloromethane: ethyl acetate (1 : 1) as eluent. The title compound (100 mg, 0.30 mmol, 48%>) was obtained as a beige foam. ESMS m/z 331 (M+H)+.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 211244-81-4, 2-(Methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one.

Reference:
Patent; AFRAXIS, INC.; CAMPBELL, David; DURON, Sergio, G.; VOLLRATH, Benedikt; WADE, Warren; WO2011/156640; (2011); A2;,
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Related Products of 55583-59-0, Adding some certain compound to certain chemical reactions, such as: 55583-59-0, name is 2,5-Diamino-4,6-dichloropyrimidine,molecular formula is C4H4Cl2N4, 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 55583-59-0.

A 50 mL, rounded bottom flask was charged with 2,5-diamino-4,6- dichloropyrimidine (390 mg, 2.2 mmoles), and 3-methyl-4-nitrobenzylamine hydrochloride (500 mg, 2.5 mmoles). The vessel was then evacuated and flushed with nitrogen, then 1-butanol (8 mL) and diisopropylethylamine (0.86 mL, 4.9 mmoles) was added via syringe. The slurried material was then heated to 120 0C (reflux) over the course of a few minutes and held at that temperature for 6 hours. The reaction was complete and clean by HPLC. Treatment with sulfuric acid or TBME, afforded oils.Use of IPA in place of 1-butanol, resulted in a slower reaction, due to the lower reflux temperature of IPA. This reaction took 12 hours and went nearly to completion with 6% of ,5-diamino-4,6-dichloropyrimidine remaining. The product precipitated from the reaction mixture and was recovered by filtration. Yield: 0.3634 g, purity 95.9%, 54 % yield

According to the analysis of related databases, 55583-59-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOGEN IDEC MA INC.; VERNALIS RESEARCH LIMITED; WO2008/88927; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 13418-77-4, 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.13418-77-4, name is 2-Amino-5-methoxypyrimidine, molecular formula is C5H7N3O, molecular weight is 125.13, as common compound, the synthetic route is as follows.

General procedure: A 0.5 – 2.0 mL microwave vessel was charged with carboxylic acid VII (251 mg, 0.534 mmol) and this was dissolved in NMP (2 mL). HATU (223 mg, 0.587 mmol) andDIPEA (0.102 mL, 0.587 mmol) were then added and the resultant mixture was stirred at room temperature for 30 min. 2-amino-5-trifluoromethylpyridine (130 mg, 0.801 mmol) was then added and the vessel was tightly sealed with a crimp top. The resultant mixture was heated thermally in a heating block to 110 C for 16 h. The mixture was then diluted with EtOAc and washed with successively with sat. NH4Cl (aq) (1X), sat. NaHCO3 (aq) (1X), H2O (1X) and brine (1X). The organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was then purified by FCC (12 g SiO2, gradient elution with 0-5% MeOH/DCM). The semi-pure material obtained was then further purified by FCC (12 g SiO2, gradient elution with 0-100% EtOAc/hexanes) and then purified further by FCC (12 g SiO2, gradient elution with 0-5% MeOH/EtOAc) to provide 170 mg (52%) of 11d.

Statistics shows that 13418-77-4 is playing an increasingly important role. we look forward to future research findings about 2-Amino-5-methoxypyrimidine.

Reference:
Article; Letourneau, Jeffrey J.; Stroke, Ilana L.; Hilbert, David W.; Cole, Andrew G.; Sturzenbecker, Laurie J.; Marinelli, Brett A.; Quintero, Jorge G.; Sabalski, Joan; Li, Yanfang; Ma, Linh; Pechik, Igor; Stein, Philip D.; Webb, Maria L.; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3601 – 3605;,
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. 287714-35-6, name is Methyl 2-chloropyrimidine-5-carboxylate. A new synthetic method of this compound is introduced below., Formula: C6H5ClN2O2

A solution of methyl 2-chloropyrimidine-5-carboxylate (200 mg, 1.16 mmol) in dichloromethane (4.00 mL) was added to a stirred solution of 1-methyl-1,4-diazepane (0.144 mL, 1.16 mmol) and N-ethyl-N-propan-2-ylpropan-2-amine (0.902 mL, 5.22 mmol) in dichloromethane (4.00 mL) at 25 C. The resulting solution was stirred at ambient temperature for 18 h. The reaction mixture was evaporated to dryness and redissolved in MeOH (20 mL) and the crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and evaporated to dryness to afford methyl 2-(4-methyl-1,4-diazepan-1-yl)pyrimidine-5-carboxylate (274 mg, 94%) as a white solid. This was used directly with no further purification. 1H NMR (399.9 MHz, DMSO-d6) delta 1.86-1.89 (2H, m), 2.26 (3H, s), 2.49-2.54 (2H, m, partially obscured by DMSO peak), 2.62-2.64 (2H, m), 3.81 (3H, s), 3.80-3.84 (2H, m), 3.89-3.91 (2H, m), 8.79 (2H, d). MS: m/z 251 (MH+)

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, 287714-35-6, Methyl 2-chloropyrimidine-5-carboxylate.

Reference:
Patent; ASTRAZENECA AB; US2008/153812; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 62802-42-0, name is 2-Chloro-5-fluoropyrimidine, molecular formula is C4H2ClFN2, 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. category: pyrimidines

To a solution of 2- chloro-5-fluoropyrimidine (10.0 g, 75.46 mmol, Sigma Aldrich) in DMF (100 mL) was added tributyl(vinyl)tin (31.1 g, 98.09 mmol) at RT. The reaction mixture was purged with N2for 5 min and Pd(PPh3)4(2.62 g, 2.26 mmol) was added. The reaction mixture was further degassed with N2for 5 min and stirred at 100 C for 24 h. After completion of the reaction (monitored by TLC), the reaction mixture was cooled to RTand quenched with water (100 mL). The aqueous layer was extracted with diethyl ether (2 x 100 mL) and the combined organic layers were washed with brine (100 mL), dried over anhydrous Na2SO4, and concentrated in vacuo to obtain the initial product which was purified by silica gel chromatography (eluent: 6% EtOAc in hexanes) to provide 400.1 (8.0 g, 85% yield) as an oil.1H NMR (400 MHz, CDCl3) delta 8.58- 8.49 (m, 2H), 6.86 (dd, J = 17.4, 10.6 Hz, 1H), 6.53 (d, J = 17.3 Hz, 1H), 5.70 (d, J = 10.6 Hz, 1H). LCMS-ESI (pos.) m/z: = 125.1.

With the rapid development of chemical substances, we look forward to future research findings about 62802-42-0.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YANG, Kevin; YEH, Wen-Chen; (700 pag.)WO2018/97945; (2018); A1;,
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