Category: pyrimidines

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,
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;,
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.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;,
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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. 4316-94-3, name is 6-Chloro-5-nitropyrimidin-4-amine. A new synthetic method of this compound is introduced below., Computed Properties of C4H3ClN4O2

4-Amino-5-nitro-6- chloropyrimidine (5.0 g, 29 mmol), 4-(l-aminoethyl)phenol (4.3 g, 32 mmol) and Et3N (4.5 mL, 3.2 g, 32 mmol) were combined in anhydrous DMF (30 mL). After stirring 2 h at 25 0C, the mixture was poured into dilute citric acid (150 mL; pH ca. 3) and the precipitated product was collected by suction filtration and washed with H2O. The solid was recrystallized from a refluxing mixture Of H2O (100 mL) and EtOH (50 mL) to yield 6.6 g (84%).

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, 4316-94-3, 6-Chloro-5-nitropyrimidin-4-amine.

Reference:
Patent; DOW AGROSCIENCES LLC; BREWSTER, William; DEMETER, David; ERICKSON, W.; LOWE, Christian; KLITTICH, Carla; NUGENT, Jaime; RIEDER, Brent; SIDDALL, Thomas; YAO, Chenglin; YERKES, Carla; ZHU, Yuanming; WO2011/25505; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 2927-71-1, 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 2927-71-1, name is 2,4-Dichloro-5-fluoropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 1; 2-Chloro-5-fluoro-N-(5-methyl-lH-pyrazol-3-yl)pyrimidin-4-amineTo a solution of 5-methyl-lH-pyrazol-3-amine (612 mg, 6.0 mmol) in absolute EtOH (10 ml) was added triethylamine (1.1 ml) and 2,4-dichloro-5-fluoropyrimidine (1.0 g, 6.0 mmol) and the resulting solution was aged at room temperature for 12 hours. The mixture was partitioned between EtOAc and water. The organic layer was washed with brine and dried. The solvents were removed under reduced pressure to give the title compound as a solid (679 mg). LC-MS: 228 [M+eta].

According to the analysis of related databases, 2927-71-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/7753; (2009); A2;,
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. 26452-81-3, name is 4-Chloro-6-methoxypyrimidine. A new synthetic method of this compound is introduced below., Safety of 4-Chloro-6-methoxypyrimidine

Example 1 90 parts by weight of phosphorus oxychloride and 10 parts by weight of 4-chloro-6-methoxypyrimidine were introduced into a stirred vessel. The mixture was heated with stirring to 100° C. and, at this temperature, 6 parts by weight of water were metered in at a constant rate over the course of 4 hours. The mixture was then stirred at 100° C. for 1 hour. After cooling to room temperature, 99.6 parts by weight of a reaction mixture whose HPLC analysis showed contents of 0.2percent 4-chloro-6-methoxypyrimidine and 9.3 parts by weight of 4,6-dichloropyrimidine were obtained.

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, 26452-81-3, 4-Chloro-6-methoxypyrimidine.

Reference:
Patent; Bayer Akitnegesellschaft; US6441170; (2002); B1;,
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.13479-88-4, name is 5,7-Dichlorothiazolo[5,4-d]pyrimidine, molecular formula is C5HCl2N3S, molecular weight is 206.0525, as common compound, the synthetic route is as follows.Computed Properties of C5HCl2N3S

A 10 mL round-bottom flask, was charged withcompound 45.3 (500 mg, 2.27 mmol, 1.00 equiv) and acetic acid-d4 (5 mL). The reaction was stirred for 24 hours at 110 C. The solids were filtered out and solvents were removed under reduced pressure to provide 450 mg (89%) of intermediate 58.1 as a yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13479-88-4, 5,7-Dichlorothiazolo[5,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; NIMBUS IRIS, INC.; ROMERO, Donna L.; MASSE, Craig E.; ROBINSON, Shaughnessy; GREENWOOD, Jeremy Robert; HARRIMAN, Geraldine; WO2015/48281; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 2927-71-1, 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. 2927-71-1, name is 2,4-Dichloro-5-fluoropyrimidine, molecular formula is C4HCl2FN2, 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.

Preparation of compound 55a: 2-chloro-5-fluoro-4-methoxypyrimidine2,4-Dichloro-5-fluoropyrimidine (515 mg, 3.08 mmol) was weighed into a 150 mL RBF, and was suspended in THF (5.0 mL). The stirring suspension was cooled to -10 C. NaOMe (250 mg, 4.63 mmol) was added in one portion at -10 C. An additional 0.5 eq of NaOMe were added and the suspension was stirred at RT for 21 h. The suspension was diluted with MeOH, and the the solvents were removed in vacuo. The crude material was purified by flash chromatography (eluting with 100%o DCM) to give 2-chloro-5- fluoro-4-methoxypyrimidine (37 mg, 0.228 mmol, 7.38 %> ) as an amorphous white solid. MS (ESI, pos. ion) m/z: 162.9 (M+l). .H NMR (400 MHz, DMSO-d6) delta ppm 8.60 (d, J=2.7 Hz, 1 H), 4.04 (s, 3 H).

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 2927-71-1, 2,4-Dichloro-5-fluoropyrimidine.

Reference:
Patent; AMGEN INC.; WANG, Hui-Ling; CEE, Victor, C.; HERBERICH, Bradley, J.; JACKSON, Claire, L., M.; LANMAN, Brian, Alan; NIXEY, Thomas; PETTUS, Liping, H.; REED, Anthony, B.; WU, Bin; WURZ, Ryan; TASKER, Andrew; WO2012/129338; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 4595-59-9, 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. 4595-59-9, name is 5-Bromopyrimidine. A new synthetic method of this compound is introduced below.

To a solution of 5-bromopyrimidine (3 g, 18.87 mmol) in Et20 (120 mL) and THF (20ml) was added cyclopropylmagnesium bromide (39.6 mL, 19.81 mmol) at 0C. The resulting white suspension was stirred at rt for lh and quenched with water (0.340 mL, 18.87 mmol) followed by addition of DDQ (4.28 g, 18.87 mmol) in THF (10ml). The resulting black mixture was stirred at room temperature overnight. The reaction mixture was extracted with EtOAc. The aqueous layer was extracted with EtOAc and the combined organic layer was washed with NaOH (IN) and brine. The crude product was purified by Biotage (0-15% EtOAc/hexanes, 1.2L) to afford the title compound (700 mg, 20%) as a yellow solid. XH NMR (500 MHz, CC13D) delta ppm 8.87 (1 H, s), 8.66 (1 H, s), 2.40-2.56 (1 H, m), 1.13-1.32 (4 H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4595-59-9, 5-Bromopyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; VELAPARTHI, Upender; FRENNESSON, David B.; SAULNIER, Mark G.; AUSTIN, Joel F.; HUANG, Audris; BALOG, James Aaron; VYAS, Dolatrai M.; WO2012/9510; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 923282-64-8, 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. 923282-64-8, name is 7-Chloro-1H-pyrazolo[4,3-d]pyrimidine. A new synthetic method of this compound is introduced below.

Compound 66: 37 (0.67 g, 2.0 mmol) was added to a solution containing 28 (0.67 g, 2.0 mmol) and Hunig’s base (1.4 mL, 8.0 mmol) in DMF (15 mL). The reaction mixture was heated to 100 C. for 1 hour. The reaction was cooled to room temperature. The reaction mixture was diluted with H2O. Extracted the aqueous layer with EtOAc. Combined the organics, dried with MgSO4, filtered, and concentrated. The crude residue was purified by column chromatography on silica gel using 10% MeOH in DCM to afford 66 (0.45 g, 54%), ES (+) MS m/e=416 (M+1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,923282-64-8, its application will become more common.

Reference:
Patent; Sunesis Pharmaceuticals, Inc.; US2007/27166; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia