Day: March 16, 2022

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. 70227-50-8, name is 2-(tert-Butyl)-4-chloro-5-nitropyrimidine, molecular formula is C8H10ClN3O2, 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 2-(tert-Butyl)-4-chloro-5-nitropyrimidine

Compound 3.4 was dissolved in MeOH (1 mL) and ammonium hydroxide solution (1.5 mL) was added. The reaction mixture was stirred overnight. After removal of excess ammonia and MeOH, the mixture was extracted with chloroform. After drying with anhydrous sodium sulfate and removal of the solvent, compound 3.5 (89 mg, ~78%) was obtained and used without further purification.

With the rapid development of chemical substances, we look forward to future research findings about 70227-50-8.

Reference:
Patent; SUNESIS PHARMACEUTICALS, INC.; WO2006/65703; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 395082-55-0, 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.395082-55-0, name is 2-Chloro-4-iodopyrimidine, molecular formula is C4H2ClIN2, molecular weight is 240.43, as common compound, the synthetic route is as follows.

A solution of 3-aminoindazole (670.5 mg, 5.0 mmol) and 2-chloro-3-iodopyrimidine (1.202 g, 5 mmol)((Chem Eur J 15, 1468 (2009)), in dry dioxan (25 mL), containing CuI (47.5 mg, 0.25 mmol) trans-1,2-diaminocyclohexane (114 mg, 1.0 mmol) and K3PO4 (1.06 g, 5 mmol) is refluxed under N2 for 24 hrs. (Bioorg Med Chem Letters 22, 4358 (2012)) The mixture is cooled to 25 C and quenched with water (50 mL) and extracted with ethyl acetate (3 x 25 mL), washed with water (2 x 25 mL) and saturated brine (25 mL), and dried over MgSO4. The solvent is removed under reduced pressure, and the residue is purified by column chromatography (Pet/EtOAc 10/1) to afford 3-amino-1-(2-chloropyrimidin-4-yl)-1H-indazole as a white solid.

Statistics shows that 395082-55-0 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-4-iodopyrimidine.

Reference:
Patent; CS PHARMASCIENCES, INC.; SONG, Yuntao; BRDIGES, Alexander, James; (524 pag.)WO2017/120429; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 53557-69-0, 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 53557-69-0, name is 6-Iodopyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

6-iodopyrimidin-4-amine (prepared as described in WO 2016071214, 5.83 g, 26.4 mmol) and (1,1,2,2,2Pentafluoroethy)(1,1OphenanthroNneKN1,KN1O)copper (15.1 g, 39.6 mmol) was suspended in dimethylformamide (95.0 mL) in a dried vial under argon. The resulting mixture was heated to 90C over night. The reaction mixture was cooled down to room temperature and filtered over Celite. The filter cake was rinsed with ethyl acetate and the resulting green suspension was washed with aqueous saturated sodium bicarbonate and ammonium hydroxide solution, and then brine. Drying over sodiumsulfate, filtration and concentration in vacuo gave the crude product which was purified by chromatography over silica gel to afford 6-(1,1,2,2,2-pentafluoroethyl)pyrimidin-4-amine. LC-MS: 214 (M+H), Rt: 0.67 min, 1H NMR (400 MHz, Chloroform) delta ppm 5.41 (br s, 2 H) 6.82 (d, J=1 .10 Hz, 1 1-1) 8.71 (s, 1 H)

According to the analysis of related databases, 53557-69-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; EDMUNDS, Andrew; RENDLER, Sebastian; MUEHLEBACH, Michel; EMERY, Daniel; (109 pag.)WO2018/206348; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 30129-57-8, 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 30129-57-8, name is 6-Methyl-1H-pyrazolo[3,4-d]pyrimidin-4(7H)-one. This compound has unique chemical properties. The synthetic route is as follows.

3-Iodo-6-methyl-1 ,5-dihydro-4H-pyrazolo[3,4-dJpyrimidin-4-one. To a stirred20 suspension of 6-methyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one (80.0 g, 533 mmol) in dimethylacetamide (800 mL) was added N-iodosuccinimide (180 g, 799 mmol) portion-wise over aperiod of 30 min. The reaction mixture vas heated to 130C for 3 hours. The reaction mixturewas cooled to 0C and poured into a saturated aqueous solution ofNa2S203 (1.8 L) with stining.The mixture was allowed to settle for 3 h and the precipitated brown solid was filtered. The25 isolated brown solid was suspended in THF:Cf:bCN:MeOH:FhO (3:3:2:3) and stirred for 16 h.The resulting solid was filtered and dried under vacuum to provide the title compound (60 g,41 ~o) as a brown solid. 1H NNIR (400 NIHz, DMSO-do) 8 13.02 (s, 1H), 12.04 (s, 1H), 2.32 (s,3H). [M+H] ‘” 276.9.

According to the analysis of related databases, 30129-57-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DART NEUROSCIENCE, LLC; GOMEZ, Laurent; VERNIER, William, Francois; (104 pag.)WO2018/125810; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 959236-97-6 , The common heterocyclic compound, 959236-97-6, name is 4-Bromo-2-(methylthio)pyrimidine, molecular formula is C5H5BrN2S, 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 stirred 30% H202 (6g, 29.4 mmol, 1 eq) was added ammonium molybdate tetrahydrate (1.09g, 0.88mmol, 0.03eq) at 0C portion wise then stirred for 20min., and then a solution of 4-bromo-2-(methylthio)pyrimidine (6g, 29.41mmol, leq) slowly added at 0C then allowed to RT for 3h. Monitored by TLC, the reaction mixture was concentrated to crude residue, which was diluted with cold water then extracted with DCM (3X100mL). The combined organic layer was washed with 5% H2SC>4 solution and water then dried over Na2SC>4 and concentrated to crude compound. The crude compound was purified by column chromatography (silica gel, 100-200 mesh) using 0-40% EtOAc in pet ether as eluent to afford 4-bromo-2- (methylsulfonyl)pyrimidine (6g, 86%) as off-white solid. LCMS: [M+H]+ 238.84.

The synthetic route of 959236-97-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ONTARIO INSTITUTE FOR CANCER RESEARCH (OICR); AL-AWAR, Rima; ZEPEDA-VELAZQUEZ, Carlos Armando; PODA, Gennady; ISAAC, Methvin; UEHLING, David; WILSON, Brian; JOSEPH, Babu; LIU, Yong; SUBRAMANIAN, Pandiaraju; MAMAI, Ahmed; PRAKESCH, Michael; STILLE, Julia Kathleen; (1053 pag.)WO2017/147700; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature 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;,
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.313339-35-4, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid, molecular formula is C6H4Cl2N2O2S, molecular weight is 239.08, as common compound, the synthetic route is as follows.name: 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid

Thionyl chloride (1.6 mL, 22.1 mmol) and DMF (0.025 mL) were added to 4,6-dichloro-2-(methylthio)-pyrimidine-5-carboxylic acid (528 mg, 2.21 mmol) obtained in Reference Example 4, and the mixture was stirred at 90C for 4 hours. The mixture was concentrated under reduced pressure, and the residue was dried for 12 hours under reduced pressure. The resulting residue was dissolved in dichloromethane (11 mL), and the mixture was stirred at -78C for 30 minutes after triethylamine (0.25 mL, 1.76 mmol), and a dichloromethane (11 mL) solution of the (S)-2-(aminomethyl)pyrrolidine-1-carboxylic acid tert-butyl ester (295 mg, 1.47 mmol) obtained in Reference Example 6 were added at -78C. Thereafter, a saturated aqueous ammonium chloride solution and ethyl acetate were added to separate the organic layer. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give (S)-N-[(1-tert-butoxycarbonylpyrrolidin-2-yl)methyl]-4,6-dichloro-2-methylthiopyrimidine-5-carboxylic acid amide (538 mg, 87%). ESI-MS: m/z 421 [M + H]+. 1H-NMR (CDCl3) delta(ppm): 1.43 (s, 9H), 1.70-2.00 (m, 3H), 2.08 (m, 1H), 2.58 (s, 3H), 3.32-3.46 (m, 3H), 3.60 (m, 1H), 4.10 (m, 1H), 8.24 (brs, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,313339-35-4, 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2163554; (2010); 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. 55405-67-9, name is 3-Bromopyrazolo[1,5-a]pyrimidine, molecular formula is C6H4BrN3, 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. Product Details of 55405-67-9

PREPARATION 107 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyrimidine [Show Image] A mixture of 3-bromopyrazolo[1,5-a]pyrimidine (1.00 g, 5.1 mmol), potassium acetate (1.78 g, 18.1 mmol) and bis(pinacolato)diboron (5.77 g, 22.7 mmol) in 1,4-dioxane (20 mL) contained in a Schlenck vessel was submitted to three vacuum-argon cycles and bis(triphenylphosphine)palladium(II) dichloride (0.180 g, 0.26 mmol) was then added. The mixture was further submitted to three vacuum-argon cycles, sealed and then was stirred and heated to 100 C. After 20 hours, the reaction mixture was cooled, evaporated and then taken up in pentane and filtered through diatomaceous earth (Celite) and the filter cake was washed with a mixture of ethyl acetate/ether (3:2). The combined filtrate and washings were evaporated and the residue was stirred with n-pentane (15 mL) at -40 C for 30 minutes. The solid was filtered, washed with cold pentane and dried in vacuo to give the title compound (1.66 g, >100%) as a solid which was used without further purification. LRMS (m/z): 246 (M+1)+.1H NMR (300 MHz, CDCl3) delta ppm 1.26 (s, 12H), 6.89 (dd, 1H), 8.44 (s, 1H), 8.63 – 8.83 (m, 2H).

With the rapid development of chemical substances, we look forward to future research findings about 55405-67-9.

Reference:
Patent; Almirall, S.A.; EP2397482; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 14001-69-5, Adding some certain compound to certain chemical reactions, such as: 14001-69-5, name is 2-Methoxy-5-nitropyrimidine,molecular formula is C5H5N3O3, 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 14001-69-5.

Under 2 atmosphere, a suspension of 2-methoxy-5-nitropyrimidine (180 mg, 1.16 mmol, 1.00 equiv) and 5% Rh/C (13.8 mg, 0.60 moll Rh) in THF (11.6 mL, 0.100 M) was stirred at 23 C. Hydrazine monohydrate (69.7 mg, 1.39 mmol, 1.20 equiv) was added dropwise. The reaction 15 mixture was stirred at 23 C for 20 min. NaHCC>3 (117 mg, 1.39 mmol, 1.20 equiv) was added, followed by dropwise addition of a solution of acetyl chloride (109 mg, 1.39 mmol, 1.20 equiv) in THF (11.6 mL, 0.120 M) . The reaction mixture was stirred at 23 C for 30 min and then filtered through a short pad of celite. The celite was washed 20 with EtOAc. The combined organic solution was concentrated in vacuo. . The residue was purified by chromatography on silica gel, eluting with hexanes : EtOAc (2:1 to 0:1 (v/v)), to afford the title compound as a gray gum (125 mg, 0.682 mmol, 59% yield). Rf = 0.33 (EtOAc). NMR Spectroscopy: NMR (700 MHz, (CD3)2SO, 25 C, delta) : 10.93 (br. s, 1H) , 25 8.81 (s, 2H) , 3.91 (s, 3H) , 2.22 (br. s., 3H) . 13C NMR (175 MHz, (CD3)2SO, 25 C, delta) : 170.7, 161.8, 151.0, 131.8, 54.9, 21.6. Mass Spectrometry: HRMS (ESI-TOF) (m/z): calcd for C7H10N3O3 ( [M + H] + ), 184.0717, found, 184.0718.

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. 14001-69-5, 2-Methoxy-5-nitropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE RESEARCH FOUNDATION FOR THE STATE UNIVERSITY OF NEW YORK; NGAI, Ming-Yu; HOJCZYK, Katarzyna, N.; (214 pag.)WO2016/57931; (2016); 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 85989-61-3, name is 5,7-Dichloroimidazo[1,2-c]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 85989-61-3

Example 17A; N6-{2-[7-Chloroimidazo[1,2-c]pyrimidin-5-yl)amino]ethyl}-3-nitropyridine-2,6-diamine 800 mg (4.13 mmol) of 5,7-dichloroimidazo[1,2-c]pyrimidine (Example 11A) are suspended in 20 ml of DMSO, and 1.62 g (4.54 mmol) of N6-(2-aminoethyl)-3-nitropyridine-2,6-diamine trifluoroacetate (Example 15A) and 1.6 g (12.38 mmol) of DIPEA are added. The mixture is heated at 120 C. for 16 h. After this time, water is added, and the precipitate which has separated out is filtered off with suction. It is washed with a little 2-propanol/water and the resulting solid is dried under high vacuum. 1.34 g (92% of theory) of the product are obtained as a solid.LCMS (method 7): Rt=1.44 min. (m/z=349 (M+H)+)1H-NMR (400 MHz, DMSO-d6): delta=8.29 (t, 1H), 8.15 (s, br, 1H), 8.09 (t, 1H), 7.95 (s, 1H), 7.93 (s, 1H), 7.69 (s, br, 1H), 7.50 (d, 1H), 6.92 (s, 1H), 5.92 (d, 1H), 3.67 (m, 4H).

With the rapid development of chemical substances, we look forward to future research findings about 85989-61-3.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; US2010/113441; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia