Pyrimidines

Adding a certain compound to certain chemical reactions, such as: 1780-31-0, 2,4-Dichloro-5-methylpyrimidine, 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, Application In Synthesis of 2,4-Dichloro-5-methylpyrimidine, blongs to pyrimidines compound. Application In Synthesis of 2,4-Dichloro-5-methylpyrimidine

A solution of concentrated NH4OH (4.4 mL) in water (20 mL) was added to a suspension of compound XIII-A-59 (2 g) and Zn (2.4 g) in benzene (8 mL). The mixture was heated to reflux overnight. After cooling to room temperature, the solution was filtered and extracted twice with ether. The combined ether solution was dried and concentrated to give 1.0 g of crude product that was more than 90percent pure thus used directly in the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1780-31-0, 2,4-Dichloro-5-methylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Kalypsys, Inc.; US2005/234046; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 22536-61-4, 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 22536-61-4, name is 2-Chloro-5-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

[000121] To a stirring solution of 2-chloro-5-methylpyrimidine 80 (5 g, 38.89 mmol) in CC (250 mL) under inert atmosphere were added N-bromosuccinimide (6.92 g, 38.89 mmol) and benzoyl peroxide (706 mg, 2.91 mmol) at RT; heated to 85 °C and stirred for 16 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was filtered. The filtrate was concentrated in vacuo to obtain the crude. The crude was purified through silica gel flash column chromatography using 7percent EtOAc/ hexanes to afford crude compound 81 (5 g, mixture of SM and product in the ratio of ~1: 1) as pale yellow solid. TLC: 20percent EtOAc/ hexanes (R/. 0.5); LC-MS: 55.30percent; 208.8 (M++l); (column; Ascentis Express C18, (50 chi 3.0 mm, 2.7 muiotaeta); RT 1.79 min. 0.025percent Aq. TFA + 5percent ACN: ACN + 5percent 0.025percent Aq. TFA, 1.2 mL/min);

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 22536-61-4, 2-Chloro-5-methylpyrimidine.

Reference:
Patent; ASSEMBLY BIOSCIENCES, INC.; INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION; TURNER, William; ARNOLD, Lee, Daniel; MAAG, Hans; BURES, Mark; (99 pag.)WO2017/48954; (2017); A1;,
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. 151266-23-8, name is 3-Iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine. A new synthetic method of this compound is introduced below., Recommanded Product: 3-Iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine

87D: Compound 87C (200 mg, 0.77 mmol), ,P0 (488 mg, 2.30 mmol), 4-phenoxybenzene boronic acid (491 mg, 2.32 mmol) and Tetrakis-(triphenylphosphine)palladium (124 mg, 0.1 1 mmol) were dissolved in 2.5 mL of dioxane in a microwave vial. The vial was sealed and the reaction mixture was heated to 180C for 10 min under microwave irradiation. The reaction mixture was partitioned between water and ethylacetate and the organic layer was separated, dried over anhydrous Na2S04, filtered and concentrated. The residue was purified by column chromatography on Si02 using MeOH/CH2C12 (0: 100 to 10:90). Compound 87D was obtained as a white powder (92 mg, 41% yield). NMR (ppm, DMSO): 8.21 (s, 1 H), 7.66 (d, J= 8.8 Hz, 2H), 7.43 (t, J= 7.9 Hz, 2H), 7.21-7.1 1 (m, 5H). LCMS (+esi): 304.2 (M+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, 151266-23-8, 3-Iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine.

Reference:
Patent; THE WALTER AND ELIZA HALL INSTITUTE OF MEDICAL RESEARCH; LUDWIG INSTITUTE FOR CANCER RESEARCH LIMITED; LESSENE, Guillaume Laurent; BAELL, Jonathan Bayldon; BURGESS, Antony Wilks; MARUTA, Hiroshi; WO2012/3544; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1224288-92-9, 5-Chloropyrazolo[1,5-a]pyrimidine-3-carbonitrile, 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, SDS of cas: 1224288-92-9, blongs to pyrimidines compound. SDS of cas: 1224288-92-9

A mixture of 5-chloropyrazolo[1,5-a]pyrimidine-3-carbonitrile (343 mg, 1.92 mmol) and 2-(2,5-difluorophenyl)pyrrolidine (Intermediate 2, 343 mg, 1.87 mmol) in DMSO (10 mL) was heated at 180 C. for 1 hour and cooled to room temperature. The reaction mixture was diluted with water and extracted with EtOAc twice. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on SiO2 (Hex:EtOAc=2:1 to 1:1) to afford 5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (611 mg, 98%) as a ivory solid. 1H-NMR (CDCl3, Varian, 400 MHz): delta 2.05-2.11 (3H, m), 2.47-2.55 (1H, m), 3.67-4.10 (2H, m), 5.20 (0.7H, s), 5.65 (0.3H, s), 5.96 (0.7H, s), 6.43 (0.3H, s), 6.69-6.73 (1H, m), 6.96-7.09 (2H, m), 8.01-8.31 (3H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1224288-92-9, 5-Chloropyrazolo[1,5-a]pyrimidine-3-carbonitrile, and friends who are interested can also refer to it.

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

Application of 582313-57-3, 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. 582313-57-3, name is 4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H3ClFN3, 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.

Vial A: Add to dry round bottom flask (purged by N2)(S,S)-DACH-naphthyltrozine ligand (1.13 g, 1.43 mmol) andPd2(dba)3.CHCl3 (493 mg, 0.48 mmol).The vial was purged four times with N2 and added DCE (50 mL,Sprayed by N2 for 30 minutes). The black solution was stirred for 30 minutes at 12°C,A red-brown solution was obtained at this time.Vial B: To dry round bottom flask(by N2 purification) BB-1 (7155 mg, 23.82 mmol) was added,4-chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine (4.5 g, 26.23 mmol) andCs2 CO3 (8.54 g, 26.2 mmol). The vial was purged with N2 five times and DCE (50 mL) was added followed by addition of the contents of vial A via syringe.The reaction was stirred at 12 °C under N2 for 24 hours. The reaction mixture was filtered and concentrated to a brown gum. The crude residue was purified by flash biotage (120 g, tannin, EtOAc/petroleum ether = 15percent) to give NN-1 (6.4 g, 76percent) as an off-white solid.

According to the analysis of related databases, 582313-57-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; KUMPF, ROBERT ARNOLD; MCALPINE, INDRAWAN JAMES; MCTIGUE, MICHELE ANN; PATMAN, RYAN; RUI, EUGENE YUANJIN; TATLOCK, JOHN HOWARD; TRAN-DUBE, MICHELLE BICH; WYTHES, MARTIN JAMES; (445 pag.)TW2018/2074; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 696-07-1, 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 696-07-1, name is 5-Iodouracil. This compound has unique chemical properties. The synthetic route is as follows.

A. Preparation of 5-iodo-2,4-dioxo-3,4-dihydro-2H-pyrimidine-l-carboxylic acid tert-butyl ester; A 500 ml single neck round bottom flask was charged with 5-iodouracil (5.0g, 21mmol) and dry acetonitrile (200ml). Dimethyl amino pyridine (26mg, 0.21mmol) was added in one portion followed by drop wise addition of di-t-butyl di carbonate (5.5g, 25.2mmol) at room temperature and stirred for 3h at room temperature. The reaction mixture was filtered and the organic layer was concentrated under vacuum. Yield = 7.1 (100%)The proton NMR data of the desired product, 5-iodo-2,4-dioxo-3,4-dihydro-2H- pyrimidine-1 -carboxylic acid tert-butyl ester, is provided below: 1H NMR (400 MHz, DMSO-d6, deltappm):CH3)

According to the analysis of related databases, 696-07-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JUBILANT BIOSYS LIMITED; WO2007/122634; (2007); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1445-39-2, 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. 1445-39-2, name is 2-Amino-5-iodopyrimidine. A new synthetic method of this compound is introduced below.

b) N-(3-((2-aminopyrimidin-5-yl)ethynyl)-2,4-difluorophenyl)-5-chloro-2-methoxypyridine-3-sulfonamide acetate A mixture of 5-chloro-N-(3-ethynyl-2,4-difluorophenyl)-2-methoxypyridine-3-sulfonamide (1.24 g), 5-iodopyrimidin-2-amine (1.15 g), dichlorobis(tricyclohexylphosphine)palladium(II) (170 mg), cesium carbonate (4.51 g) and DMSO (16.5 mL) was stirred under a nitrogen atmosphere at 120 C. for 3 hr. After cooling to room temperature, the mixture was diluted with water/saturated brine and extracted three times with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated to give a residue. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound as a crude purified product in a free form. The obtained title compound as a crude purified product in a free form was dissolved in DMF/toluene and subjected to silica gel column chromatography (NH, methanol/ethyl acetate) to elute a byproduct. Silica gel supporting a free form of the title compound was added to ethyl acetate (100 mL), acetic acid (18 mL) and water (100 mL), and the mixture was stirred at room temperature for 10 min. The mixture was filtered and silica gel on the filter was treated 4 times with ethyl acetate/acetic acid (30 mL/6 mL) to elute the object product. The organic layer was collected from the filtrate, and the organic layer was washed with water and saturated brine, dried over magnesium sulfate and concentrated to give a residue. The residue was dissolved in an ethyl acetate/THF/saturated aqueous sodium hydrogen carbonate solution, and the obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate and concentrated to give a residue. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) and washed with ethyl acetate to give the title compound as a crude purified product in a free form. The same reaction was performed at 4.05-fold amount and 4.12-fold amount. The obtained title compounds as crude purified products in a free form were collected, acetic acid (24.8 mL) was added and the mixture was heated to 50 C. To the mixture was added DMSO (66 mL) at 50 C. and dissolved therein. The mixture was filtered, and a trace amount of an insoluble material on the filter was washed with acetic acid (24.8 mL). The filtrate was heated to 50 C. and water (50 mL) was added dropwise. The mixture was cooled to room temperature over 30 min. The precipitate was collected by filtration, washed three times with ethanol/water (1/10, 33 mL) and dried at 50 C. under reduced pressure to give the title compound (5.53 g). 1H NMR (300 MHz, DMSO-d6) delta 1.91 (3H, s), 3.94 (3H, s), 7.14-7.37 (4H, m), 8.07 (1H, d, J=2.6 Hz), 8.43 (2H, s), 8.52 (1H, d, J=2.6 Hz), 10.46 (1H, s), 11.94 (1H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1445-39-2, 2-Amino-5-iodopyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; FUJIMOTO, Jun; LIU, Xin; KURASAWA, Osamu; TAKAGI, Terufumi; CARY, Douglas Robert; BANNO, Hiroshi; ASANO, Yasutomi; KOJIMA, Takuto; (159 pag.)US2019/169166; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 1439-10-7, 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. 1439-10-7, name is 4-Amino-5-bromopyrimidine, molecular formula is C4H4BrN3, 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.

Steps 1-3 A mixture of N-Boc-6-bromoindoline (0.66 g, 2.2 mmol), bis(pinacolato)diboron (1.118 g, 4.4 mmol), KOAc (0.65 g, 6.6 mmol.), and PdCl2(dppf) (0.069 g, 0.08 mmol) in dioxane (8 mL) was heated at 100 C. for 1.5 h in a 15 mL sealed tube and then cooled to RT. The reaction was treated with 4-amino-5-bromopyrimidine (0.76 g, 4.4 mmol) and aqueous K2CO3 (4 mL, 1M) and heated at 100 C. overnight. The mixture was diluted with aqueous K2CO3 and extracted with DCM. The organic extracts were dried over MgSO4 and concentrated. Chromatography (0-10% of (9:1 MeOH/NH3) in CH2Cl2) afforded 3A (657 mg) as a brown oil.

According to the analysis of related databases, 1439-10-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SCHERING CORPORATION AND PHARMACOPEIA, LLC; PHARMACOPEIA, INC.; US2010/197562; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 213265-83-9, name is 4,6-Dichloro-5-fluoropyrimidine, the common compound, a new synthetic route is introduced below. SDS of cas: 213265-83-9

Sodium hydride (90 mg, 60% oil dispersion) was added to a mixture of 5-{[(2R,5R)-2,5-dimethylpyrrolidin-1-yl]methyl}-4-[3-fluoro-5-(trifluoromethyl)phenyl]-1,3-thiazol-2-amine (300 mg), 4,6-dichloro-5-fluoropyrimidine (165 mg),and dehydrated tetrahydrofuran (6.0 mL) in an argon atmosphere under ice-methanol bath cooling, followed by stirringat 0C for 30 minutes. The resultant was extracted with ethyl acetate after adding ice water to the reaction mixture. Theorganic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated underreduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) toobtain 6-chloro-N-(5-{[(2R,5R)-2,5-dimethylpyrrolidin-1-yl]methyl}-4-[3-fluoro-5-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl)-5-fluoropyrimidin-4-amine (391 mg) as a solid.

The synthetic route of 213265-83-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Astellas Pharma Inc.; TAKAHASHI, Taisuke; TANAKA, Hiroaki; AKAIWA, Michinori; NEGORO, Kenji; MIHARA, Hisashi; FUJI, Hideyoshi; TAKAMATSU, Hajime; (133 pag.)EP3196200; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 10070-92-5, 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. 10070-92-5, name is Pyrimidine-5-carbaldehyde. A new synthetic method of this compound is introduced below.

Example P-5 A: Preparation of 5-propionyl-pyrimidine; 5.6 g of pyrimidine-5-carboxaldehyde in 100 ml of ether are slowly added dropwise, at 0-5C, to 18 ml of 3M ethylmagnesium bromide solution in ether. The yellowish suspension is stirred for 1 hour at 5C and then 30 ml of saturated NH4CI are added, with cooling. The phases are separated and the reaction solution is extracted 3 times with diethyl ether. The combined organic phases are washed with brine, filtered and concentrated. 3.14 g of a yellow oil are obtained, which-as the crude product-is reacted further. The intermediate is dissolved in 100 ml of methylene chloride and, after adding 10.26 g (1.2 eq. ) of pyridinium dichromate, is stirred for 20 hours at room temperature. The reaction mixture is filtered over Hyflo. The organic phase is washed with H2O/brine, dried and concentrated. After chromatography of the crude product on silica gel using ethyl acetate/hexane (1: 2), 0.95 g of the title product is obtained in the form of a colourless oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10070-92-5, Pyrimidine-5-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WO2005/47281; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia