Pyrimidines

5177-27-5, 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. 5177-27-5, name is 5-Amino-2,4-dichloropyrimidine, the common compound, a new synthetic route is introduced below.

A solution of 3.2 g of 5-amino-2,4-dichloropyrimidine in 50 ml of ethyl acetate was added to a mixture of 25 ml of a saturated aqueous solution of sodium hydrogencarbonate and 25 ml of water. A solution of 4.9 g of 3,5-dimethyl-4-methoxybenzoyl chloride was added at room temperature over a period of 15 min, and the mixture was mixed intensively for 4 h. Then the layers were separated and the aqueous layer was extracted twice with ethyl acetate. After drying over sodium sulfate and filtration the solvent was removed in vacuo to give 7.54 g of raw product. The raw product was triturated with 25 ml of isopropanol. After filtration and washing with 10 ml of isopropanol 2.74 g of the title compound were obtained as a white solid.

Statistics shows that 5177-27-5 is playing an increasingly important role. we look forward to future research findings about 5-Amino-2,4-dichloropyrimidine.

Reference:
Patent; SANOFI; Kadereit, Dieter; Schaefer, Matthias; Hachtel, Stephanie; Dietrich, Axel; Huebschle, Thomas; Hiss, Katrin; US2013/72502; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

5413-85-4, 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. 5413-85-4, name is 5-Amino-4,6-dichloropyrimidine, molecular formula is C4H3Cl2N3, 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.

Synthesis of Compound 11.1. A mixture of 4,6-dichloropyrimidin-5-amine (10 g, 6.09 mmol) and methyl amine (20 mL, 40% solution in water) in 1,4 dioxane was heated (80 C.). After 16 hr, the reaction mixture was cooled (0 C.), the solid was filtered, washed with water (2¡Á100 mL), and dried to afford compound 11.1 (8 g, 83%) as white solid. 1H-NMR (200 MHz, DMSO-d6) delta 7.73 (s, 1H), 6.82 (bs, 1H), 4.92 (bs, 2H), 2.87 (d, J=4.4 Hz, 3H). MS m/z 159 [M+1]+.

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. 5413-85-4, 5-Amino-4,6-dichloropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sunesis Pharmaceuticals, Inc; US2009/5359; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

2435-50-9, 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 2435-50-9 as follows.

To a stirred mixture of pyrimidine-4-carbaldehyde (2 g, 18.5 mmol, 1.0 eq.) and hydrazinecarbothioamide (2.02 g, 22.2 mmol, 1.2 eq.) in ethanol (20 mL) and water (20 mL) was added concentrated hydrochloric acid (100 iL) and the reaction heated at 70 C for 4 hours. After cooling to room temperature the precipitate was collected by filtration, washed with ethanol and then dried in air to afford 2-(pyrimidin-4- ylmethylene)hydrazinecarbothioamide as a brown solid (2.1 g, 62% yield). NMR (400 MHz, DMSO) 11.93 (IH, s), 9.21 (IH, d, J=1.3 Hz), 8.86 (IH, d, J=5.3 Hz), 8.59 (IH, s), 8.43 (IH, s), 8.39 (IH, dd, J=1.3, 5.3 Hz), 8.03 (IH, s).

The chemical industry reduces the impact on the environment during synthesis 2435-50-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GENKYOTEX SA; MACHIN, Peter; SHARPE, Andrew; LOCK, Christopher James; CHAMBERS, Mark S; HODGES, Alastair; ALLEN, Vivienne; ELLARD, John M; (189 pag.)WO2016/98005; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

49845-33-2 , The common heterocyclic compound, 49845-33-2, name is 2,4-Dichloro-5-nitropyrimidine, molecular formula is C4HCl2N3O2, 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 2,4-dichloro-5-nitropyrimidine (500 mg, 2.5 mmol) dissolved in tetrahydrofuran (10 mL), sodium hydroxide (238 mg, 2.8 mmol) and aqueous ammonia (0.3 mL) was added, and reacted for 2 hrs at 55¡ãC. The solvent was removed under reduced pressure, and the residue was separated by flash column chromatography (dichloromethane: methanol=100:1), to obtain Compound w: 2-chloro-5-nitro-4-aminopyrimidine as a white solid (0.47 g, yield 84percent). MS(ESI)m/z: [M+H]+=175.

According to the analysis of related databases, 49845-33-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Huilun Life Science & Technology Co., Ltd; FAN, Xing; QIN, Jihong; (43 pag.)EP3284743; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 5305-59-9, 6-Chloropyrimidin-4-amine, 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, 5305-59-9, blongs to pyrimidines compound. 5305-59-9

A mixture of 6-chloropyrimidin-4-amine (6.5 g, 0.050 mol), 4,4,5, 5-feframethyl-2-vinyl-l,3,2-dioxaborolane (9.24 g, 0.060 mol), fefrafc(triphenylphosphine)- palladium(O) (3.9 g, 0.0030 mol) and sodium carbonate (21 g, 0.20 mol) in dioxane (300 mL) and H20 (30 mL) was stirred at 90 C under nitrogen for 15 hours. The mixture was concentrated under reduced pressure and the residue was partitioned between EtOAc (400 mL) and water (150 mL). The organic layer was separated, dried over Na2S04, and concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with DCM/MeOH (20: 1) to give the desired product as a white solid (4.8 g, 80% yield). LCMS (ESI) m/z: 122.1 [M+H+].

With the rapid development of chemical substances, we look forward to future research findings about 5305-59-9.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLENCH, Toby; ELLWOOD, Charles; GOODACRE, Simon; LAI, Yingjie; LIANG, Jun; MACLEOD, Calum; MAGNUSON, Steven; TSUI, Vickie; WILLIAMS, Karen; ZHANG, Birong; WO2012/35039; (2012); 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. 1753-50-0, name is 2-Chloropyrimidine-5-carbonitrile. A new synthetic method of this compound is introduced below., 1753-50-0

To a solution of (S)-2-amino-4-(((S)-2-fluoro-3-methoxypropyl) (4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl) butyl)amino) butanoic acid hydrochloride (120 mg, 277 mumol) in THF (2 mL) and H2O (0.5 mL) was added NaHCO3 (70 mg, 831 mumol), and then 2-chloropyrimidine-5-carbonitrile (43 mg, 305 mol) and the resulting mixture was stirred at 70 C. for 1 h and then allowed to cool to rt. The mixture was adjusted to pH=6 by the addition of 1 M aq. HCl and then concentrated in vacuo. The crude residue was purified by reverse phase prep-HPLC to give the title compound. LCMS (ESI+): m/z=500.2 (M+H)+. 1H NMR (400 MHz, Methanol-d4) delta ppm 8.56 (br s, 1H) 8.45 (br s, 1H) 7.42 (br d, J=7.28 Hz, 1H) 6.52 (d, J=7.50 Hz, 1H) 4.75 (br d, J=3.31 Hz, 1H) 4.51 (t, J=5.84 Hz, 1H) 3.57 (d, J=3.97 Hz, 1H) 3.49-3.53 (m, 1H) 3.37-3.46 (m, 2H) 3.33-3.37 (m, 3H) 2.84-2.96 (m, 2H) 2.65-2.83 (m, 8H) 2.15-2.24 (m, 1H) 2.04-2.14 (m, 1H) 1.87-1.94 (m, 2H) 1.81 (br dd, J=13.78, 6.73 Hz, 2H) 1.58-1.69 (m, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1753-50-0, 2-Chloropyrimidine-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Pliant Therapeutics, Inc.; CHA, Jacob; DONG, Chengguo; HOM, Timothy; JIANG, Lan; LEFTHERIS, Katerina; LI, Hui; MORGANS, JR., David J.; MUNOZ, Manuel; REILLY, Maureen; ZHENG, Yajun; (232 pag.)US2019/276449; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

135481-57-1, Adding a certain compound to certain chemical reactions, such as: 135481-57-1, 6-Benzyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4(1H,3H)-dione, 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, 135481-57-1, blongs to pyrimidines compound.

6-Benzyl-5,6,7,8-tetrahydropyrido-[4,3-d]pyrimidine-2,4 (1H, 3H) -dione (30.0 g, 0.116 mol) prepared according to Process Step 1 was mixed with phosphorus oxychloride (300 mL), followed by stirring with heating for five hours. After checking the completion of the reaction by thin layer chromatography, excess phosphorus oxychloride was distilled off under reduced pressure. The residue was mixed with isopropyl alcohol (300 mL) for crystallization. The suspension containing the precipitated crystals was stirred under reflux for one hour and was further stirred at room temperature for one hour. The precipitated crystals were collected by filtration, were dried under reduced pressure and thereby yielded 6-benzyl-2,4-dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimid ine hydrochloride (33 g, in a yield of 85%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,135481-57-1, its application will become more common.

Reference:
Patent; KYOWA HAKKO KOGYO CO., LTD.; EP1552842; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

5413-85-4 , The common heterocyclic compound, 5413-85-4, name is 5-Amino-4,6-dichloropyrimidine, molecular formula is C4H3Cl2N3, 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.

2C. 5,6-Diamino-4-chloropyrimidine; A mixture of 4,6-dichloro-5-aminopyrimidine (Aldrich Chemical Co.) (2.0 g, 12.2 mmol) and concentrated aqueous ammonia (20 ml) was heated to 100 0C in a sealed glass tube with vigorous stirring for 18 hours. The cooled tube was recharged with concentrated aqueous ammonia (8 ml), aggregates were broken up, and the mixture was reheated at 100 0C for a further 28 hours. The mixture was evaporated to dryness and the solids were washed with water (20 ml) and dried to give the product as yellow crystals (1.71 g, 97percent). LC/MS (LCTl): Rt 1.59 [M+H]+ 147, 145.

According to the analysis of related databases, 5413-85-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; THE INSTITUTE OF CANCER RESEARCH:ROYAL CANCER HOSPITAL; CANCER RESEARCH TECHNOLOGY LIMITED; ASTRAZENECA AB; WO2008/75110; (2008); 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. 934524-10-4, name is 2,4-Dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below., 934524-10-4

To a solution of the 2,4-dichloro-N-tosylpyrrolopyrimidine 3 (1.00 g, 2.92 mmol) in 1,4-dioxane (40 mL) and H2O (10 mL) was added phenylboronic acid (430 mg, 3.50 mmol) and Na2CO3 (620 mg, 5.84 mmol), and the mixture was degassed under argon. To this mixture was added Pd(PPh3)4 (100 mg, 6 mol %) and the reaction mixture was heated at reflux for 1 h, then cooled to room temperature and the solvent was removed in vacuo. The residue was dissolved in EtOAc (50 mL) and washed with H2O (2 * 30 mL), brine (2 * 30 mL), dried, filtered and the solvent was removed in vacuo to give a yellow residue. The residue was purified by flash chromatography (10% EtOAc/Hexanes) and recrystallised from EtOH to give 5d (600 mg, 55%) as a white solid; mp 151-155 C; deltaH (CDCl3): 8.14 (2H, d, J 8.0 Hz), 7.97 (2H, dd, J 6.0, 2.0 Hz), 7.75 (1H, d, J 4.0 Hz), 7.52-7.51 (3H, m), 7.34 (2H, d, J 8.0 Hz), 6.87 (1H, d, J 4.0 Hz), 2.41 (3H, s); deltaC (CDCl3): 160.6, 155.3, 152.9, 146.3, 136.0, 134.2, 131.1, 129.9, 129.0, 128.8, 127.1, 116.3, 104.1, 21.7; m/z (ESI): 384.0 (M[35Cl]H+), 386.0 (M[37Cl]H+); HRMS (ESI): M[35Cl]H+, found 384.0567. C19H15ClN3O2S+ requires 384.0569.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,934524-10-4, 2,4-Dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Article; O’Brien, Nathan J.; Brzozowski, Martin; Buskes, Melissa J.; Deady, Leslie W.; Abbott, Belinda M.; Bioorganic and Medicinal Chemistry; vol. 22; 15; (2014); p. 3879 – 3886;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding some certain compound to certain chemical reactions, such as: 871254-61-4, name is 2,4-Dichloropyrimidine-5-carbaldehyde, 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 871254-61-4. 871254-61-4

Example 18 6-Chloro-1H-pyrazolo[3,4-d]pyrimidine To a stirred solution of hydrazine (Aldrich, 64 mg, 2 mmol) in THF (5 mL), 2,4-Dichloro-pyrimidine-5-carbaldehyde (Example 17, 176 mg, 1 mmol) was added and the mixture was stirred at room temperature for 30 min. The mixture was poured into water and extracted with EtOAc. The extract was dried with sodium sulfate and the solvent was removed to give an orange solid. 128 mg, 82%. MS (M+H)+, 155.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 871254-61-4.

Reference:
Patent; Ding, Qingjie; Jiang, Nan; Roberts, John Lawson; US2005/277655; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia