Day: June 17, 2021

Application of 1254710-16-1, Adding some certain compound to certain chemical reactions, such as: 1254710-16-1, name is 8-Bromo-7-chloro-2-phenyl-[1,2,4]triazolo[1,5-c]pyrimidine,molecular formula is C11H6BrClN4, 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 1254710-16-1.

General procedure: A mixture of 5a (0.16 g, 0.5 mmol), the appropriate amine (1.5mmol, 3.0 equiv), and Et3N (0.51 g, 5 mmol) in anhydrous MeOH(15 mL) was stirred under reflux for 24 h until full consumption ofthe substrates. The progress of the reaction was monitored by TLC(eluent: PE-EtOAc, 3:1). Then, the mixture was concentrated underreduced pressure. The residue was directly subjected to columnchromatography on silica gel using PE-EtOAc (8:1) as the eluent toafford, respectively, the desired 7,8-bis(amino)-substituted[1,2,4]triazolo[1,5-c]pyrimidines 6g and 6h.

According to the analysis of related databases, 1254710-16-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Tang, Caifei; Wang, Chao; Li, Zhiming; Wang, Quanrui; Synthesis; vol. 46; 20; (2014); p. 2734 – 2746;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 17119-73-2, 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 17119-73-2, name is 4-Chloro-6-methyl-2-(methylthio)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

[00195] Ethyl 3-iodo-i-methylcyclopentanecarboxylate (5.60 g, 19.9 mmol) was dissolved in dimethylacetamide (66 mL) in a pressure vessel under a stream of nitrogen. Rieke Zinc (28.6 mL of a 5Omg/mL suspension in THF, 21.8 mmol) was added quickly via syringe. The vessel was capped and stirred at ambient temperature for 15 minutes. The vessel was opened under a stream of nitrogen and 4-chloro-6-methyl-2- (methylthio)pyrimidine (4.16 g, 23.8 mmol) was added followed by PdCl2dppf (1.09 mg, 1.49 mmol). The vessel was capped and heated to 80 C for 2 h. The reaction mixture was then cooled to room temperature, diluted with ethyl acetate, and filtered through celite. The filtrate was transferred to a separatory funnel and washed with water (3x), brine, and dried over sodium sulfate. The dried solution was filtered, and the filtrate was concentrated. The residue was purified by flash-column chromatography on silica gel (gradient elution, 0 to 100% ethyl acetate-hexanes) to give ethyl 1-methyl- 3 -(6-methyl-2-(methylthio)pyrimidin-4-yl)cyclopentane- 1 -carboxylate (2.1 g, 36%) as a mixture of cis and trans isomers. The isomers were separated by preparative HPLC (column: Phenomenex Gemini C18 250*5Omm*10 um; mobile phase: 45-70% water [0.05% ammonia hydroxide v/v]-ACN) to give ethyl (1R,3R and 1S,3S)-1-methyl-3-(6- methyl-2-(methylthio)pyrimidin-4-yl)cyclopentane- 1 -carboxylate (700 mg) as a colorless oil. MS (ES+) C,5H22N2025 requires: 294, found: 295 [M+H]. ?H NMR (400 IVIFIz, CDC13): ppm 6.67 (s, 1H), 4.17 (q, J= 7.2 Hz, 2H), 3.27-3.18 (m, 1H), 2.61- 2.53 (m, 4H), 2.42 (s, 3H), 2.30-2.23 (m, 1H), 2.14-2.05 (m, 1H), 2.02-1.91 (m, 1H),1.8 1-1.72 (m, 2H), 1.38 (s, 3H), 1.29 (t, J= 7.2 Hz, 3H).

According to the analysis of related databases, 17119-73-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; BRUBAKER, Jason, D.; DIPIETRO, Lucian, V.; (105 pag.)WO2018/22761; (2018); 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. 49845-33-2, name is 2,4-Dichloro-5-nitropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 49845-33-2

(a) ChlorobonitrQineTo a solution of 2,4-dichloro-5-nitro-pyrimidine (1.00 g; 5.2 mmol) in methanol (30 mL) was added dropwise a solution of sodium methoxide (278 mg, 5.2 mmol) in methanol (5mL) at-10 C. The reaction mixture was stirred for 10 minutes at -10 C. Acetic acid (5 mL) wasadded and the mixture was allowed to warm to room temperature. After evaporation of themixture, the residue was partitioned between 5% NaHCO3-solution and ethyl acetate. The ethyl acetate layer was washed with water, brine, dried over sodium sulfate and evaporated in vacuo. The residue was purified by column chromatography (heptane/ethyl acetate 4/1 v/v%) to obtain 281.9 mg (29%) of 2-chloro-4-methoxy-5-nitro-pyrimidine.

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, 49845-33-2, 2,4-Dichloro-5-nitropyrimidine.

Reference:
Patent; NETHERLANDS TRANSLATIONAL RESEARCH CENTER B.V.; DE MAN, Adrianus Petrus Antonius; BUIJSMAN, Rogier Christian; STERRENBURG, Jan Gerard; UITDEHAAG, Joost Cornelis Marinus; DE WIT, Joeri Johannes Petrus; ZAMAN, Guido Jenny Rudolf; WO2015/155042; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.504-17-6, name is 4,6-Dihydroxy-2-mercaptopyrimidine, molecular formula is C4H4N2O2S, molecular weight is 144.1518, as common compound, the synthetic route is as follows.Application In Synthesis of 4,6-Dihydroxy-2-mercaptopyrimidine

General procedure: A mixture of aldehyde (0.25 mmol), 2-thiobarbituric acid(0.5 mmol), ammonium acetate (0.3 mmol) and CuFe2O4 (10 mol%)in distilled H2O was stirred for an appropriate time. After completionof the reaction (monitored by TLC), the resulted precipitatewasfiltered and dissolved in hot methanol and the catalyst was separatedand collected by an external magnetic and washed withacetone and EtOH several times and dried in an oven at 70 C toreuse in next reactions. The pure solid product was obtained viaevaporation the 2/3 of methanol and filtration. The solid productwas recrystallized from water/ethanol as solvent to afford the pureproducts. All of the products were identified by physical andspectroscopic data. White powder; M.P: 240 C decompose. IR (KBr) n (cm1): 3432(NH), 3108 (CeH, sp2 stretch), 1623, 1687 (C]O), 1433, 1544 (C]C,Ar). 1H NMR (DMSO-d6, 400 MHz) d (ppm): 6.01 (s, 1H), 6.91e7 (m,3H), 7.08e7.12 (m, 4H), 11.49e11.75 (m, 4H), 17 (s, 1H). 13C NMR(DMSO-d6, 100 MHz) d (ppm): 26.88, 95.44, 115.26, 123.60, 127.61,130.05, 130.48, 159.60, 162.03, 163.32, 173.24. Anal. Calcd forC15H12FN5O2S2: C, 47.74; H, 3.20; N, 18.56, %; Found C, 47.76; H,3.24; N, 18.60%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,504-17-6, 4,6-Dihydroxy-2-mercaptopyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Naeimi, Hossein; Didar, Asieh; Journal of Molecular Structure; vol. 1137; (2017); p. 626 – 633;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 187035-79-6, 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. 187035-79-6, name is Ethyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate. A new synthetic method of this compound is introduced below.

The intermediate 8-(((tert-butyldiphenylsilyl)oxy)methyl)- 1 -isopropyl-7- (methylsulfonyl)- l,2,3,4-tetrahydropyrazino[l,2-a]indole was prepared following a procedure analogous to that described in Preparation 4. The mixture of compound 8-(((tert- butyldiphenylsilyl)oxy)methyl)- l-isopropyl-7-(methylsulfonyl)-l, 2,3,4- tetrahydropyrazino[l,2-a] indole (0.19 mmol), ethyl 2-chloro-4-(trifluoromethyl)pyrimidine- 5-carboxylate (97 mg, 0.38 mmol) and DIEA (100 mu,, 0.57 mmol) in j-PrOH / CH2C12 (1 mL / 0.5 mL) was stirred at 50C for 8 h. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel eluting with EtOAc/hexanes (1/1) to give racemic ethyl 2-(8-(hydroxymethyl)- l-isopropyl-7-(methylsulfonyl)-3,4- dihydropyrazino[ 1 ,2-a]indol-2( lH)-yl)-4-(trifluoromethyl)pyrimidine-5-carboxylate. LC- MS m/z 563 [M+Na]+. 1H NMR (400 MHz, CD3OD): delta 9.31 (s, 1H), 8.11 (s, 1H), 7.80 (s, 1H), 6.55 (s, 1H), 6.02 – 5.92 (m, 1H), 5.23 – 5.17 (m, 1H), 5.07 (s, 2H), 4.52 – 4.47 (m, 1H), 4.34 (q, J = 7.2 Hz, 2H), 4.19 – 4.06 (m, 1H), 4.00 – 3.93 (m, 1H), 3.27 (s, 3H), 2.42 – 2.32 (m, 1H), 1.36 (t, J = 7.2 Hz, 3H), 1.18 (d, J = 6.8 Hz, 3H), 1.03 (d, J = 6.8 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,187035-79-6, Ethyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; DONG, Chengguo; FAN, Yi; LEFTHERIS, Katerina; LOTESTA, Stephen; SINGH, Suresh, B.; TICE, Colin; ZHAO, Wei; ZHENG, Yajun; ZHUANG, Linghang; WO2013/138568; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 353272-15-8, 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. 353272-15-8, name is 6-Chloro-5-iodopyrimidin-4-amine, molecular formula is C4H3ClIN3, 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 mixture of (5 -2-(l-amiiioethyl)-5-chloro-3-cyclopropylquinazolin-4(3H)- one (50 mg, 0.189 mmoi ), 6-chloro-5-iodopyrimidin-4-amine (48 mg, 0.189 mmoi) and DIPEA (49 mg, 0.379 mmoi) in n-BuOH (1 mL) was heated to reflux and stirred further for 16 hours, then cooled to rt, and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/MeOH (v/v) = 100/1 ) to give the title compound as a yellowish solid (49 mg, yield 53%). MS (ESI, pos. ion) m/z: 483.0 [M+H]+; FontWeight=”Bold” FontSize=”10″ H NMR (400 MHz, CDC13) delta (ppm): 7.98 (s, 1H), 7.55-7.53 (m, 2H), 7.43-7.41(dd, J = 3.6, 5.6 Hz, 1H), 6.41-6.39 (d, J= 7.8 Hz, 1H), 6.12-6.05 (m, 1H), 5.04 (s, 2H), 3.05-3.03 (m, 1H), 1.59- 1.57 (d, J= 6.2 Hz, 3H), 1.43-1.41 (m, 2H), 1.14-1.10 (m, 1H), 0.95-0.86 (m,lH).

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 353272-15-8, 6-Chloro-5-iodopyrimidin-4-amine.

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD.; XI, Ning; WANG, Liang; WANG, Tingjin; WU, Weibin; (123 pag.)WO2015/175579; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 90914-41-3, name is 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C5H2BrClN4

Bromopyrazolopyrimidine (8) To a 25 mL recovery flask were added 6 (230 mg, 0.708 mmol, 1.05 eq.), THF (10 mL), Et3N (470 muL, 3.37 mmol, 5.0 eq.), and chloropyrazolopyrimidine 7 EPO (157 mg, 0.674 mmol, 1.0 eq.). The reaction mixture was stirred at reflux for 1.5h. The reaction was concentrated and diluted with EtOAc (50 mL) and NaHCO3 (sat’d aq., 50 niL). The organic layer was washed with H2O (50 mL) and brine (50 mL). The combined aqueous layers were extracted with EtOAc (2 x 50 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated to give a light-brown oil that slowly solidified to a white solid (308 mg crude). The crude material was purified via flash chromatography (10% to 20% CH3OH/CH2C12) to give a colorless oil (205 mg, 58%).Observed M+H: 523.1 (Br isotope)NMR, DMSO-d6, HCl salt : deltaltheta.40 (s, IH), 8.30 (s, IH), 7.49 (d, 2H), 7.26 (d, 2H), 4.88 (s, IH), 4.59 (m, 2H), 4.50 (obs m, 2H), 3.34-3.23 (m, 4H), 3.07-3.03 (m, 2H), 2.73 (s, 6H), 1.94 (d, 2H), 1.38-1.34 (m, 2H) ppm.

With the rapid development of chemical substances, we look forward to future research findings about 90914-41-3.

Reference:
Patent; EXELIXIS, INC.; WO2006/71819; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 3680-71-5 , The common heterocyclic compound, 3680-71-5, name is 1,7-Dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one, molecular formula is C6H5N3O, 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: Preparation of 5-bromo-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one: (0344) [00156] To a stirred solution of 3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one (5.5 g, 40.7 mmol) in N,N-dimethyl formamide (100 mL), N-(bis-trimethylsilyl)acetonitrile(18.22 g, 89.55 mmol) and N-bromo succinimide (7.24 g, 40.7 mmol) were added and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was quenched with cold water (1000 mL) and stirred for 30 minutes. The precipitated solid was filtered and dried under suction to afford title compound 5-bromo-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one (6.26 g, crude) as brown solid. Calculated (M+H): 213.9; Found (M+H): 214.0

The synthetic route of 3680-71-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LUC THERAPEUTICS; ANDERSON, David, R.; VOLKMANN, Robert, A.; MENNITE, Frank, S.; FANGER, Christopher; (390 pag.)WO2017/100591; (2017); 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. 14001-67-3, name is 5-Bromo-2-methylthiopyrimidine, molecular formula is C5H5BrN2S, 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 5-Bromo-2-methylthiopyrimidine

Step 1: 2-Methylsulfanyl-5-phenylethynyl-pyrimidine Bis-(triphenylphosphine)-palladium(II)dichloride (120 mg, 0.16 mmol, 0.05 equiv.) were dissolved in 50 ml THF and 5-bromo-2-methylsulfanyl-pyrimidine (840 mg, 4.1 mmol) and phenylacetylene (410 mu, 4.1 mmol, 1 equiv.) were added at room temperature. Triethylamine (1.36 ml, 12.3 mmol, 3 equiv.), triphenylphosphine (28 mg, 0.12 mmol, 0.03 equiv.) and copper(I)iodide (19 mg, 0.08 mmol, 0.03 equiv.) were added and the mixture was stirred for 3 hours at 65C. The reaction mixture was cooled and extracted once with saturated NaHCC”3 solution and three times with ethyl acetate. The organic layers were combined, dried with sodium sulfate, filtered and evaporated to dryness. The crude product was purified by flash chromatography on silicagel (heptane: ethyl acetate 100:0 -> 50:50). The desired 2- Methylsulfanyl-5-phenylethynyl-pyrimidine was obtained as a light yellow solid (400 mg, 44%), MS: m/e = 227.3 (M+H+).

With the rapid development of chemical substances, we look forward to future research findings about 14001-67-3.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; JAESCHKE, Georg; LINDEMANN, Lothar; RICCI, Antonio; RUEHER, Daniel; STADLER, Heinz; VIEIRA, Eric; WO2013/50460; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 6623-81-0 , The common heterocyclic compound, 6623-81-0, name is 2,4-Dihydroxy-5-methoxypyrimidine, molecular formula is C5H6N2O3, 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 compound 104 (2.8 g, 20 mmol) in dry acetonitrile (30 ml_) was added BSA (21 g, 1 00 mmol, 5 eq). The reaction mixture was stirred at 60 C for 4 h and cooled to room temperature. To this reaction mixture were added compound 1 03 (1 0.1 g, 20 mmol), TMSOTf (10.8 m l_, 60 mmol, 3eq), and the resulted reaction mixture was stirred at 60 C for 4 h. Upon completion of the reaction as monitored by TLC, the reaction mixture was treated with methylene chloride and saturated sodium bicarbonate. The organic phase was separated, and the aqueous phase was extracted with dichloromethane. The combined organic phase was dried over anhydrous Na2S04. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The crude product was purified by flash chromatography on a silica gel column giving 1 1 g desired compound 105 in 95% yield.

The synthetic route of 6623-81-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MODERNA THERAPEUTICS, INC.; ROY, Atanu; CONLEE, Christopher, R.; DE FOUGEROLLES, Antonin; FRALEY, Andrew, W.; WO2014/93924; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia