Pyrimidines

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.5018-38-2, name is 4,6-Dichloro-5-methoxypyrimidine, molecular formula is C5H4Cl2N2O, molecular weight is 179, as common compound, the synthetic route is as follows.Recommanded Product: 4,6-Dichloro-5-methoxypyrimidine

To a solution of 4-hydroxyphenylethylamine hydrochloride (300 mg) in Nu,Nu-dimethyl formamide (DMF, 5 mL) was added diisopropylethylamine (355 mg, 2 equiv.). The solution was stirred for 5 min before the addition of 4,6-dichloro-5-methoxypyrimidine (249 mg, 1 equiv.). The reaction mixture was then stirred for 16 h at room temperature before it was concentrated in vacuo. The residue was dissolved in DMF (10 mL) and was stirred with sodium hydride (66 mg, 2.2 equiv.) for 20 min at room temperature. Another portion of 4,6-dichloro-5-methoxypyrimidine (269 mg, 1 .2 equiv.) was introduced into the reaction mixture, which was then left to stir at room temperature for 48 h. The DMF was then removed in vacuo and the product was purified by flash silica column chromatography to afford 178 mg (31 % yield) of the product as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5018-38-2, 4,6-Dichloro-5-methoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BASF SE; BASF SCHWEIZ AG; GRAMMENOS, Wassilios; CRAIG, Ian Robert; BOUDET, Nadege; MUeLLER, Bernd; DIETZ, Jochen; LAUTERWASSER, Erica May Wilson; LOHMANN, Jan Klaas; MONTAG, Jurith; WO2013/113863; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1445-39-2, 2-Amino-5-iodopyrimidine, 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, 1445-39-2, blongs to pyrimidines compound. COA of Formula: C4H4IN3

g) N-(3-((2-aminopyrimidin-5-yl)ethynyl)-2-chlorophenyl)-5-chloro-2-methoxypyridine-3-sulfonamide A mixture of 5-chloro-N-(2-chloro-3-ethynylphenyl)-2-methoxypyridine-3-sulfonamide (185 mg), 5-iodopyrimidin-2-amine (149 mg), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (17.4 mg), copper(I) iodide (9.9 mg), triethylamine (0.72 mL) and DMSO (1.83 mL) was stirred under microwave irradiation at 100 C. for 1 hr. After cooling to room temperature, the mixture was diluted with water/saturated brine and extracted 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. The obtained crude purified product of the title compound was subjected to silica gel column chromatography (NH, methanol/ethyl acetate) to elute a byproduct. Silica gel supporting the title compound was added to ethyl acetate (20 mL), acetic acid (4 mL) and water (20 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 (6 mL/1.2 mL) to elute the object product. The organic layer was collected from the filtrate, and the organic layer was washed with water and 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 subjected to ethyl acetate/hexane and the precipitate was collected by filtration to give the title compound (31 mg). 1H NMR (300 MHz, DMSO-d6) delta 3.88 (3H, s), 7.24 (2H, brs), 7.31-7.38 (2H, m), 7.44-7.52 (1H, m), 8.03 (1H, d, J=2.6 Hz), 8.42 (2H, s), 8.48-8.52 (1H, m), 10.37 (1H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1445-39-2, its application will become more common.

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;,
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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 175791-49-8, name is 5-Bromo-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. name: 5-Bromo-7H-pyrrolo[2,3-d]pyrimidine

[00303] Step 1: Synthesis of 5-bromo-7-(methylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine. To a solution of 5-bromo-7H-pyrrolo[2,3-d]pyrimidine (or any other suitable aromatic halide, 1 mmol) in DMF (5 mL) was added NaH (43 mg, 60%, 1.1 mmol) at 0oC, After 5 min., MsCl* (114 mg, 1.0 mmol) was added and the mixture was stirred at 0oC for 1h. The mixture was diluted with EtOAc (20 mL), successively washed with water (20 mL) and brine (20 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by chromatographic column on silicagel to give 5-bromo-7-(methylsulfonyl)- 7H- pyrrolo[2,3-d]pyrimidine (265 mg, 95% yield). ESI- LCMS (m/z): 275.9 [M+1]+.[00304] *Alternatively, other alkylating, acylating, carbamoylating, or sulfonylating agents can be employed is similar manner.

With the rapid development of chemical substances, we look forward to future research findings about 175791-49-8.

Reference:
Patent; EPIZYME, INC.; CHESWORTH, Richard; MORADEI, Oscar, Miguel; SHAPIRO, Gideon; JIN, Lei; BABINE, Robert, E.; (495 pag.)WO2016/44641; (2016); A2;,
Pyrimidine | C4H4N2 – PubChem,
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Adding a certain compound to certain chemical reactions, such as: 1012785-51-1, 2,4-Dichloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine, 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, 1012785-51-1, blongs to pyrimidines compound. Application In Synthesis of 2,4-Dichloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine

[00491] A mixture of 2,4-dichloro-5-iodo-7H-pyrrolo[2,3-djpyrimidine (0.66 g, 2.1 mmol, 1.0 eq), 4- methylbenzenesulfonyl chloride (0.46 g, 2.4 mmol, 1.1 eq), triethylamine (0.40 mL, 29 mmol, 1.4 eq), and DMAP (0.033 g, 0.27 mmol, 0.13 eq) in 4 mL of dichloromethane was stirred at room temperature for 1 hr. The reaction mixture was diluted with dichloromethane and washed with iN HC1 (2X), followed by a wash with saturated aqueous sodium bicarbonate. The worked-up solution was dried over MgSO4, filtered, rotary evaporated, and dried under vacuum giving 1.1 g of yellow solid as the crude 2,4-dichloro-5-iodo-7-tosyl- 7H-pyrrolo [2,3 -d]pyrimidine. LC-MS: M+H=467. 7.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1012785-51-1, its application will become more common.

Reference:
Patent; PHARMACYCLICS LLC; CHEN, Wei; JIA, Zhaozhong, J.; THOMAS, William, D.; WONE, David; (190 pag.)WO2017/205762; (2017); A1;,
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Pyrimidine – Wikipedia

Related Products of 57489-77-7, 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. 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.

Under nitrogen protection, 60% NaH (1.36g, 34mol) was slowly added to 60mL of cold N, N-dimethylformamide.The temperature was controlled to about 0 C, and 2-isopropylsulfonylaniline (4.10 g, 20.6 mmol) was slowly added, and the mixture was kept under stirring for 0.5 hours.To the above solution was added a solution of 5,7-dichloropyrazolo [1,5-a] pyrimidine (3.20 g, 17.0 mmol) in 10 mL of N, N-dimethylformamide,The reaction solution was slowly raised to room temperature and heated to 60 C for 8 hours.The reaction solution was poured into ice water, a solid was precipitated, and the crude product was filtered and dried.The crude product was recrystallized from isopropanol to obtain 4.10 g of 5-chloro-N- [2- (isopropylsulfonyl) phenyl] pyrazolo [1,5-a] pyrimidin-7-amine (c),The yield was 68.7%.

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 57489-77-7, 5,7-Dichloropyrazolo[1,5-a]pyrimidine.

Reference:
Patent; Liaoning University; Liu Ju; Shi Jiantao; Chen Ye; Ding Shi; Wang Yang; Gong Yilin; Wang Zhen; Li Jie; (16 pag.)CN110483526; (2019); A;,
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. 17573-78-3, name is 4,5,6-Trifluoropyrimidine. A new synthetic method of this compound is introduced below., name: 4,5,6-Trifluoropyrimidine

Example 1-3; 0.5 g of 4,5,6-trifluoropyrimidine, 0.38 g of 2-pentyn-l-ol and 0.62 ml of triethylamine were added to 1 ml EPO of toluene, then the mixture was stirred at room temperature for 1 hour. Then the reaction mixture was subjected to silica gel column chromatography to obtain 0.53 g of 4,5-difluoro-6-(2-pentynyloxy)pyrimidine. 1H-NMR: 1.15(t,3H), 2.26(qt,2H), 5. ll(t,2H) , 8.26(s,lH)

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, 17573-78-3, 4,5,6-Trifluoropyrimidine.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2006/51891; (2006); 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. 22325-27-5, name is 2-Mercapto-4,6-dimethylpyrimidine, molecular formula is C6H8N2S, 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. COA of Formula: C6H8N2S

General procedure: The intermediates M1-4 were synthesized according to previously reported methods [8,9]. A solution of thiol (1 mmol) was prepared in 1% aqueous NaOH (5 mL). Then, we added, dropwise, 1 mL of halogenated-methyl flavonoids, M1-4 (1 mmol), in DMF. The mixture was heated to 90 C in an oil bath; alternatively it was sealed, and then irradiated in a Smith Creator microwave at 50-100 W to 90 C. After completion of the reaction, the mixture was diluted with water (40 mL) and the precipitate was filtered. Finally, the precipitate was recrystallized from an appropriate solvent to give the title compounds, 5-8.

With the rapid development of chemical substances, we look forward to future research findings about 22325-27-5.

Reference:
Article; Huang, Wei; Chen, Qiong; Yang, Wen-Chao; Yang, Guang-Fu; European Journal of Medicinal Chemistry; vol. 66; (2013); p. 161 – 170;,
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Pyrimidine – Wikipedia

Related Products of 1421372-67-9, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 1421372-67-9 as follows.

Compound 7 from the previous step, iron (12.8 g), and ammonium chloride (1.42 g) were heated in ethanol (100 mL) and water (30 mL) at reflux for 1.5 h. The mixture was cooled and filtered. The solids were rinsed with DCM. The filtrate was concentrated to approximately 20 mL and NaOH (1 N, 50 mL) was added. The gray precipitates were filtered off and rinsed with DCM. The mixture was partitioned and the organic layer was washed with NH4OH (50 mL), brine (100 mL) and concentrated to a brown foam (compound 8, 12 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1421372-67-9, its application will become more common.

Reference:
Patent; NEUFORM PHARMACEUTICALS, INC.; CHAORAN, Huang; CHANGFU, Cheng; (85 pag.)WO2017/117070; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 13509-52-9, 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. 13509-52-9, name is 1,3,6-Trimethylpyrimidine-2,4(1H,3H)-dione. A new synthetic method of this compound is introduced below.

1,3,6-Trimethylpyrimidine-2,4(1H,3H)-dione (step 1) (5 g, 32.4 mmol) and chlorobenzene (50 mL) were charged to a 3 necked flask, and the vessel evacuated with nitrogen. Benzoyl chloride (commercial) (11.2 mL, 97 mmol) was added followed by zinc (II) chloride (5 g, 36.7 mmol) in one portion and the reaction was then heated to 110 C. for 16 h. The reaction was cooled to RT then poured into water (100 mL) and EtOAc (100 mL). The layers were separated and the aqueous extracted with EtOAc (2×150 mL). The combined organics were washed with water (100 mL) and dried (Na2SO4), filtered under reduced pressure and evaporated to leave an orange solid. The solid was washed with hexane followed by hot diethyl ether, affording the product as an off white solid. The mother liquors were further purified by chromatography on silica, eluting with 10%-100% EtOAc/hexane. The title product was obtained as a pale orange solid; [1758] 1H NMR (400 MHz, CDCl3) delta 7.89 (2H, dd), 7.60 (1H, t), 7.48 (2H, t), 3.52 (3H, s), 3.38 (3H, s), 2.26 (3H, s); [1759] LCMS Rt=0.80 min [M+H]+ 259 (Method 2minLC_v003).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13509-52-9, 1,3,6-Trimethylpyrimidine-2,4(1H,3H)-dione, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; AHMED, Mahbub; ASHALL-KELLY, Alexander; GUERITZ, Louisa; MCKENNA, Jeffrey; MCKENNA, Joseph; MUTTON, Simon; PARMAR, Rakesh; SHEPHERD, Jon; WRIGHT, Paul; US2014/171417; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 57489-77-7, 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 57489-77-7, name is 5,7-Dichloropyrazolo[1,5-a]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Example 7 Synthesis of 5-chloro-N-cyclopropylpyrazolo[1,5-a]pyrimidin-7-amine To 5,7-dichloropyrazolo[1,5-a]pyrimidine (200 mg, 1.06 mmol) in ACN was added Et3N (148 mul, 1.06 mmol) and cyclopropylamine (75 mul, 1.06 mmol). The reaction was refluxed at 80 C. overnight. The mixture was concentrated under reduced pressure, dissolved in DCM, and washed with water. The resulting organic layer was dried over Na2SO4 and concentrated under reduced pressure to afford 156 mg of 5-chloro-N-cyclopropylpyrazolo[1,5-a]pyrimidin-7-amine (70% yield). LCMS (M+1=209)

According to the analysis of related databases, 57489-77-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SENHWA BIOSCIENCES, INC.; Haddach, Mustapha; Tran, Joe A.; Pierre, Fabrice; Regan, Collin F.; Raffaele, Nicholas; Ravula, Suchitra; Ryckman, David M.; (417 pag.)US9303033; (2016); B2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia