Pyrimidines

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. 1436686-17-7, name is Ethyl 5-bromopyrazolo[1,5-a]pyrimidine-3-carboxylate. A new synthetic method of this compound is introduced below., HPLC of Formula: C9H8BrN3O2

To a solution of cyclopropylboronic acid (174mg, 2.1mmol), KOAc (330mg, 3.4mmol), ethyl 5-bromopyrazolo[l,5-a]pyrimidine-3-carboxylate (500mg, 1.7mmol) in dioxane (15ml) was added PdCl2(dppf).DCM (138mg, 0.17mmol). The reaction mixture was stirred at 90 C for 2.5 h under a nitrogen atmosphere and then concentrated in vacuo. The residue was diluted with water and then extracted with DCM (20 x 3). The combined organic layers were washed with brine and dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/EA (v/v) = 6/1) to give the title compound as a brown solid (220 mg, 57%). H NMR (300 MHz, CDC1 ): delta (ppm) 8.51 (d, J = 7.2 Hz, 1H), 8.47 (s, 1H), 6.78 (d, J = 7.2 Hz, 1H), 4.39 (q, J= 7.1 Hz, 2H), 2.25-2.16 (m, 1H), 1.41 (t, J= 7.1 Hz, 3H), 1.33-1.25 (m, 2H), 1.25- 1.14 (m, 2H).

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, 1436686-17-7, Ethyl 5-bromopyrazolo[1,5-a]pyrimidine-3-carboxylate.

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD.; XI, Ning; LI, Minxiong; LI, Xiaobo; WO2015/73267; (2015); A1;,
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Electric Literature of 1195-08-0, 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.1195-08-0, name is 2,4-Dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde, molecular formula is C5H4N2O3, molecular weight is 140.1, as common compound, the synthetic route is as follows.

To a slurry of 400mg of 5-formyluracil (2.8 mM) in DMF (10 mL) at room temperature was added sodium hydride (280 mg, 7 mM, 60% in oil). After stirring for 30 min., MeI (1.013 g, 7.2 mM) was added. When the turbid reaction mixture became a homogeneous yellow solution tlc revealed the absence of starting uracil. The reaction mixture was treated with MeOH and water, concentrated on the rotovap and the residue partitioned between MeOH and hexane. The MeOH fraction was concentrated and the residue partitioned between chloroform and water. The organic phase dried (MgSO4), filtered and concentrated to give 420 mg (89% yield) of 1,3-dimethyl-5-formyluracil as an off-white waxy solid. 1H-NMR (DMSO-d6), delta=9.82 (s, 1H), 8.52 (s, 1H), 3.43 (s, 3H), 3.2 (s, 3H). LC/MS; rt=0.34 mins. m/z=169, [M+H]+.

Statistics shows that 1195-08-0 is playing an increasingly important role. we look forward to future research findings about 2,4-Dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde.

Reference:
Patent; Wyeth; US2006/19965; (2006); A1;,
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Synthetic Route of 2164-84-3, 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. 2164-84-3, name is 4,6-Diamino-5-nitropyrimidine. A new synthetic method of this compound is introduced below.

0022; 0025; 0027; 0030; 0032; 0035; 0037; 0040

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2164-84-3, its application will become more common.

Reference:
Patent; Nanjing Puruida Pharmaceutical Technology Co., Ltd.; Wang Xiaobo; (6 pag.)CN110407757; (2019); A;,
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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. 57489-77-7, name is 5,7-Dichloropyrazolo[1,5-a]pyrimidine, molecular formula is C6H3Cl2N3, 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. name: 5,7-Dichloropyrazolo[1,5-a]pyrimidine

To a solution of 5, 7-dichloro-pyrazolo[l,5-a]pyrimidine (1.0 mmol) and 2- 0’sopropylsulfonyl)aniline(1.0 mmol) in 5 mL of DMF, was added carefully NaH (24 mg). The resulting suspension was stirred at 500C for 2 hours. After cooling at RT and careful quenching (ice), water was added and the mixture was extracted with EtOAc. The organic layers were collected, dried (Na2SO4), filtrated and concentrated. The residue was purified over SiO2 column chromatography (eluent: 9: 1 Hexane: EtOAc), to give the desired 5-chloro-N-(2- (isopropylsulfonyl)phenyl)pyrazolo[l,5-a]pyrimidin-7-amine. MS (ES+): 351.06 (M+l)+.

With the rapid development of chemical substances, we look forward to future research findings about 57489-77-7.

Reference:
Patent; IRM LLC; WO2009/126514; (2009); A1;,
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Electric Literature of 1189169-37-6, 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. 1189169-37-6, name is 1-(5-Bromopyrimidin-2-yl)ethanone, molecular formula is C6H5BrN2O, 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.

5-Bromo-2-(1,1-difluoroethyl)pyrimidine 1-(5-bromopyrimidin-2-yl)ethanone (304 mg, 1.514 mmol) in anhydrous DCM (50 ml), under nitrogen, was treated w Diethylaminosulfur trifluoride (1220 mg, 1 ml, 7.57 mmol). After 12 hours of stirring additional Diethylaminosulfur trifluoride (610 mg, 0.5 ml, 3.75 mmol) was added. This was repeated again after 24 hours, Diethylaminosulfur trifluoride (610 mg, 0.5 ml, 3.75 mmol). After 36 hours the reaction was quenched with sat. NaHCO3 and extracted with AcOEt, washed with Brine and dried over Na2SO4, filtered and concentrated. The reaction was purified by column chromatography on silica gel (petroleum ether: EtOAc=1:0 to 0:1) to afford 5-bromo-2-(1,1-difluoroethyl)pyrimidine (298 mg, 88% yield). 1H NMR (CDCl3 500 MHz): delta 8.92 (s, 21-1), 2.08 (t, 2H).

According to the analysis of related databases, 1189169-37-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; H. Lundbeck A/S; Kilburn, John Paul; Rasmussen, Lars Kyhn; Jessing, Mikkel; Eldemenky, Eman Mohammed; Chen, Bin; Jiang, Yu; US2014/107335; (2014); A1;,
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Electric Literature of 1005-37-4 ,Some common heterocyclic compound, 1005-37-4, molecular formula is C5H7ClN4, 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.

Step 1 : A mixture of 6-chloro-4-N-methylpyrimidine-2,4-diamine (48 mg, 0.30 mmol), 3-(dihydroxyboranyl)benzoic acid (60 mg, 0.36 mmol), K2C03 (104 mg, 0.75 mmol) and palladium tetrakis(triphenylphosphine)palladium (0) (17 mg, 0.015 mmol) in 1 ,4-dioxane (3 mL) and water (1 mL) was heated in a sealed tube at 90C for 15 h. Concentrated and purified by preparative HPLC. LCMS [M+H]+ 245.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1005-37-4, its application will become more common.

Reference:
Patent; THOMAS HELLEDAYS STIFTELSE FOeR MEDICINSK FORSKNING; SCOBIE, Martin; WALLNER, Olov; KOOLMEISTER, Tobias; VALLIN, Karl Sven Axel; HENRIKSSON, Carl Martin; HOMAN, Evert; HELLEDAY, Thomas; JACQUES, Sylvain; DESROSES, Matthieu; JACQUES-CORDONNIER, Marie-Caroline; FISKESUND, Roland Julius Yu; (359 pag.)WO2015/187089; (2015); A1;,
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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. 1197953-49-3, name is (2-((2,5-Dichloropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide. This compound has unique chemical properties. The synthetic route is as follows. Safety of (2-((2,5-Dichloropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide

Compound 33 (224 mg, 0.6 mmol), compound 5 (189 mg, 0.6 mmol) and ethylene glycol monomethyl ether (3 mL) were added to a 25 mL single-necked flask equipped with a magnetic stirring and a condensing tube, and the mixture was stirred and dissolved.A hydrogen chloride isopropanol solution (0.9 mmol, 0.18 mL, 5 M) was added dropwise, and the mixture was heated to 120 C under a nitrogen atmosphere and stirred overnight. Cool to room temperature and add water(10 mL) and saturated sodium bicarbonate (5 mL), dichloromethane (15 mL¡Á3),Dry over sodium sulfate, filter, concentrate, residue over silica gel220mg, the yield is 56.2%

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, 1197953-49-3, (2-((2,5-Dichloropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide.

Reference:
Patent; Shenzhen Tajirui Bio-pharmaceutical Co., Ltd.; Wang Yihan; Li Huanyin; (67 pag.)CN109369721; (2019); A;,
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Reference of 3764-01-0, 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 3764-01-0, name is 2,4,6-Trichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Take 5000ml three bottles, with mechanical mixing, condenser. Feeding: 2,4.6-trichloropyrimidine (molecular weight: 182,010 mol), 28.1 g of benzene boronic acid (molecular weight: 122, 0.23 mol), 12.0 g (0.0104 mol) of tetraphenylphenylphosphine, 60 g of potassium carbonate (0.435 mol ), Tetrahydrofuran 600ml, toluene 400ml, water 400ml. start mechanical agitation, Under the conditions of reduced pressure ventilation 3 times to maintain Ar gas protection, with TLC (thin layer chromatography) to monitor the reaction, After 8 hours of reflux, the reaction was complete. Let cool, the reaction body divided into two layers, separated from the organic layer, evaporated, The solid product was obtained and recrystallized from toluene to give 19.9 g of intermediate M2-1, molecule The amount of 266, the yield of 75%.

According to the analysis of related databases, 3764-01-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kunshan Weixinnuo Display Co., Ltd.; Tsinghua University; Beijing Weixinnuo Technology Co., Ltd.; Qiu Yong; Wang Xing; Li Yinkui; Duan Lian; Ren Xueyan; (104 pag.)CN103665014; (2017); B;,
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Synthetic Route of 114040-06-1 , The common heterocyclic compound, 114040-06-1, name is 3-Bromo-5,7-dichloropyrazolo[1,5-a]pyrimidine, molecular formula is C6H2BrCl2N3, 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 3-bromo-5,7-dichloropyrazolo[l,5-a]pyrimidine (5.0 g, 19 mmol) in DCM (50 mL) was added cyclopropylmethanamine (1.48 g, 21 mmol), and DIPEA (6.6 mL, 38 mmol). The reaction was stirred at rt for 2 h. Water and DCM were added to separate the phases and the aqueous phase was extracted with DCM. The combined organic extracts were dried over NaSC>4, filtered and concentrated. The crude product was purified by flash chromatography (gradient: EtO Ac/hex 0-50%) to give the title compound as a yellow solid (5.25 g, 92%). NMR (400 MHz, CDCl3) delta ppm 7.97 (s, 1H), 6.50 (br. s, 1H), 5.97 (s, 1H), 3.25 (dd, J = 7.3, 5.5 Hz, 2H), 1.26-1.13 (m, 1H), 0.74-0.65 (m, 2H), 0.37 (q, J= 5.0 Hz, 2H); MS ESI [M + H]+ 301.0, calcd for [Ci0Hi0BrClN4 + H]+ 301.0.

The synthetic route of 114040-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY HEALTH NETWORK; LAUFER, Radoslaw; NG, Grace; LI, Sze-Wan; PAULS, Heinz W.; LIU, Yong; PATEL, Narendra Kumar B.; WO2015/70349; (2015); A1;,
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Application of 2802-62-2, Adding some certain compound to certain chemical reactions, such as: 2802-62-2, name is 4,6-Difluoropyrimidine,molecular formula is C4H2F2N2, 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 2802-62-2.

4-Amino-phenol (0.135 g, 1.21 [MMOL)] is added in one portion to a suspension of NaH (60% free-flowing powder moistened with oil, 58.2 mg, 1.45 mmol, 1.2 equiv) in dioxane abs. (1.4 mL), under an argon atmosphere. When hydrogen evolution subsides, a solution of 4,6- [DIFLUORO-PYRIMIDINE] (0.141 g, 1.21 [MMOL)] in dioxane (0.4 mL) is added. The resulting dark mixture is stirred for 1.5 h at rt, quenched by addition of MeOH (2 mL) and concentrated in vacuo. After addition of CH2CI2, the resulting suspension is filtered and concentrated in vacuo. The residue is purified by silica gel column chromatography [(CH2CI2/ET2O,] 90/10, then 85/15) to afford the title compound as a white solid : ES-MS: 204.0 [M+H] [+] ; single peak at [TR=] 4. 96 min (System 2); Rf = 0.30 [(CH2CI2/ET20,] 85/15).

According to the analysis of related databases, 2802-62-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2003/99771; (2003); A2;,
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