Category: pyrimidines

Reference of 40497-30-1, 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. 40497-30-1, name is 2-Methylpyrimidine-4,6(1H,5H)-dione. A new synthetic method of this compound is introduced below.

4,6-dichloro-2-methylpyrimidine (1.63 g, 10.0 mmol) prepared based on the method described in Production Example 2A above using 2-methyl-1H-pyrimidine-4,6-dione instead of the 2-ethyl-1H-pyrimidine-4,6-dione, was slowly added to a 2-ethoxyethanol (5.0 mL) solution of 3-aminophenol (1.09 g, 10.0 mmol) and the reaction mixture heated for 4 hours at 130C. The reaction was monitored by thin layer chromatography and, following the end of the reaction, the reaction mixture was cooled to room temperature and the precipitated white powder filtered off. The crude product filtered off was used in the subsequent reaction without further purification (1.76 g, crude yield 75%).1H NMR spectrum (DMSO, 400 MHz), delta : 2.42(3H, s), 6.50(1H, m), 6.73(1H, s), 7.05(1H, m), 7.12(1H, m), 7.19(1H, s), 10.00(1H, s). Mass spectrum (EI), m/z: 234 (M-H+)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,40497-30-1, its application will become more common.

Reference:
Patent; Sankyo Company, Limited; EP1473289; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 115932-00-8 , The common heterocyclic compound, 115932-00-8, name is Ethyl pyrazolo[1,5-a]pyrimidine-3-carboxylate, molecular formula is C9H9N3O2, 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 a solution of pyrazolo [1,5-a] pyrimidine-3-carboxylic acid ethyl ester (3.15 g, 16.4 mmol)In ethanol (50 mL) and water (40 mL)Aqueous potassium hydroxide (2M, 40 mL) was added,The resulting reaction was stirred at 50 C for 2 hours,Cool to room temperature and concentrate under reduced pressure. A 1 M aqueous solution of dilute hydrochloric acid was added to the resulting reaction mixture to adjust to pH = 2. A white solid appeared and was filtered. The filter cake was collected to give the title compound as a white solid (2.6 g, 97%).

The synthetic route of 115932-00-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; (88 pag.)CN104650092; (2017); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 6960-17-4, 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. 6960-17-4, name is 2,5-Dimethoxypyrimidin-4-amine, molecular formula is C6H9N3O2, 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.

To the filtrate was added 1.3 g of 2,5-dimethoxy-4-aminopyrimidine,Reacting at 20 C to 30 C for 5 to 8 hours,HPLC analysis,After completion of the reaction,crystallization,To give yellow crystals of ethyl 4- [4- (2,5-dimethoxypyrimidinyl)] – 3-thiourea,2.3 g, purity 99%Yield of about 92%.

According to the analysis of related databases, 6960-17-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jiangsu Fuding Chemical co., LTD; LIU, DONG WEI; (6 pag.)CN103739606; (2016); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 85989-61-3, 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. 85989-61-3, name is 5,7-Dichloroimidazo[1,2-c]pyrimidine. A new synthetic method of this compound is introduced below.

5,7-Dichloroimidazo[1,2-f]pyrimidine (100 mg, 0.5 mmol) and 3-amino-5-methyl pyrazole (52 mg, 0.5 mmol) were stirred in ethanol (1 ml) at 60 C. for 15 minutes. Alternatively, the pyrimidine and the pyrazole can be reacted in DMF at 100-150 C. for 15-30 minutes. The solvent was evaporated and the residue purified by flash chromatography using 1:1 EtOAc:Hexane then 1:10 MeOH/DCM. Evaporation of the solvent revealed 7-chloro-N-(5-methyl-1H-pyrazol-3-yl)imidazo[1,2-f]pyrimidin-5-amine (100 mg, 75%). 1H NMR (400 MHz, DMSO) delta 10.54 (s, 1H) 8.37 (s, 1H) 7.57 (s, 1H) 7.07 (s, 1H) 6.48 (s, 1H) 2.28 (s, 3H). [M+H] calc’d for C10H9ClN6, 249; found, 249.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,85989-61-3, its application will become more common.

Reference:
Patent; Dong, Qing; Hosfield, David J.; Paraselli, Bheema R.; Scorah, Nicholas; Stafford, Jeffrey A.; Wallace, Michael B.; Zhang, Zhiyuan; US2006/84650; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1513-69-5, 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. 1513-69-5, name is 2-Amino-4-hydroxy-6-(trifluoromethyl)pyrimidine. A new synthetic method of this compound is introduced below.

Example 15: 4-chloro-6-(trifluoromethyl)pyrimidin-2-amine (24)2-Amino-6-(trifluoromethyl)pyrimidin-4-ol (200 mg, 1.1 mmol) is dissolved in POCI3 (3 eq., 0.3 ml_, 3.3 mmol) and dimethylaniline (0.28 ml_, 2 eq.) is added. The reaction mixture is heated at 7O0C for 4 h. The resulting mixture is poured into a mixture of ice-water, and the resulting precipitate is collected to yield the desired compound 24 in 59%. ESI-MS m/z 198 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1513-69-5, 2-Amino-4-hydroxy-6-(trifluoromethyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; COVALYS BIOSCIENCES AG; WO2006/114409; (2006); 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.13040-89-6, name is 5-Chloro-6-methylpyrimidin-4-amine, molecular formula is C5H6ClN3, molecular weight is 143.57, as common compound, the synthetic route is as follows.Product Details of 13040-89-6

To a solution of 1,1-dimethylethyl (25)-2-(3-bromo-2-oxopropyl)-l-piperidinecarboxylate D2 (0.10 g, 0.31 mmol) in DMF (1.50 ml) was added 5-chloro-6-methyl-4-pyrimidinamine (available from Chemstep No.19785) (0.049 g, 0.34 mmol) and the reaction mixture was stirred at 80 0C for 4 h. The solvent was removed under reduced pressure and the residue was taken-up in Et2O. The organic phase was washed with water, dried (Na2SO4), filtered and evaporated under reduced pressure. The residue was eluted through a SCX column to afford a crude material (0.021 g) containing the title compound D7, the corresponding N- Boc protected derivative and some residual 5-chloro-6-methyl-4-pyrimidinamine. [N-Boc derivative data. UPLC: rt = 0.71 min, peaks observed: 365 (M+l, 100%) and 367 (M+l, 33%). C18H25ClN4O2 requires 364]. The crude was dissolved in DCM (1 ml) and TFA (2 ml) was added dropwise. The reaction was left under stirring for 1 h at room temperature. Volatiles were removed under reduced pressure and the residue eluted through a SCX column (500 mg) to afford the title compound D7 (0.018 g)contaminated with some residual 5-chloro-6-methyl-4-pyrimidinamine. UPLC: rt = 0.40 min, peaks observed: 265 (M+l, 100%) and 267 (M+l, 33%). C13Hi7ClN4 requires 264.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13040-89-6, 5-Chloro-6-methylpyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/3997; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 96225-80-8, 6-Morpholinopyrimidin-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, SDS of cas: 96225-80-8, blongs to pyrimidines compound. SDS of cas: 96225-80-8

2-(6-Morpholin-4-yl-pyrimidin-4-ylamino)-thiazole-5-carbonitrile (22-9) 6-Morpholin-4-yl-pyrimidin-4-ylamine (185 mg, 1.03 mmol) was stirred in 5 mL anhydrous THF under N2. Sodium hydride (82 mg, 60% dispersion, 2.05 mmol) was added and the reaction was warmed to 45 C. for 5 minutes. 2-chloro-thiazole-5-carbonitrile (208 mg, 1.44 mmol) was added and the reaction was heated to reflux. After 30 minutes added additional 2-chloro-thiazole-5-carbonitrile (85 mg, 0.59 mmol). After an additional 1 hour the reaction was cooled to room temperature, quenched with water and the THF was removed in vacuo. The mixture was neutralized with 1 M HCL and the resulting precipitate was filtered and washed with water. The solid was suspended in DMSO, filtered and washed with EtOAc to provide the title compound. 1-NMR (400 MHz, CD3OD) 8.44 (1H,s), 7.95 (1H,s), 6.13 (1H,s), 3.81 (t, 4H, J=5.0 Hz), 3.63 (t, 4H, J=4.9 Hz). M+1=289.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,96225-80-8, 6-Morpholinopyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; Bilodeau, Mark T.; Hartman, George D.; Hoffman JR., Jacob M.; Sisko, John T.; Manley, Peter J.; Smith, Anthony M.; Tucker, Thomas J.; Lumma JR., William C.; Rodman, Leonard; US2002/137755; (2002); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 22404-46-2, 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 22404-46-2 as follows.

A 100 mL round-bottomed flask was charged with 3- (4- (piperidin-1-yl) styryl) -2-fluoro-5- (4, 4, 5, 5-tetramethyl- 1, 3, 2-dioxaborolan-2-yl) pyridine (199 mg, 0.49 mmol), A- chloro–7~methylpyrimidin-2-amine (146 mg, 1.016 mmol) and EPO Pd(PPh3)^ (59 mg, 50.9 mumol) . Then toluene (20 mL) , EtOH (10 rtiL) and 2M aq. K2CO3 (1.53 mL, 3.05 mmol) were added and the reaction mixture was immersed in an oil bath at 120 0C for 1 h. The reaction mixture was partitioned between EtOAc (30 mL) and water ( 50 mL) and the organic layer was dried (MgSO4), filtered and concentrated and then quickly filtered through silica ( MeOH/CH?C^ gradient) . After evaporation of volatiles the residue was dissolved in dioxane (8 mL) and water (3 mL) and concentrated HCl (0.66 mL) was added. The reaction mixture was heated to 110 0C for 70 min and then evaporated. Purification by reverse phase preparative HPLC (eluting with aq. TFA/MeCN) gave the title compound (40 mg, 21%) as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22404-46-2, its application will become more common.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2007/27528; (2007); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 6312-72-7, name is 2,6-Diamino-5-bromopyrimidin-4(1H)-one. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 2,6-Diamino-5-bromopyrimidin-4(1H)-one

(p). diethyl N-(6-[([2,6-diamino-4(3H)-oxopyrimidin-5-yl]thio)methyl]-4,5,6,7-tetrahydrobenzothieno-2-yl)glutamate This material was prepared using the procedure described in example 2(g). From diethyl N-[6-(thiomethyl)-4,5,6,7-tetra-hydrobenzothieno-2-yl]glutamate 8(o) (3.00 g, 7.3 mmol) and 5-bromo-2,6-diamino-4(3H)-pyrimidinone (1.44 g, 7.0 mmol) there was obtained a yellow solid (712 mg, 19%) melting at 122-128. The following analyses indicated that the product was diethyl N-(6-[([2,6-diamino-4(3H)-oxopyrimidin-5-yl]thio)methyl]-4,5,6,7-tetrahydrobenzothieno-2-yl)glutamate. NMR (DMSO-d6) delta=9.92 (1H, s), 8.53 (1H, d, J=7.5 Hz), 7.54 (1H, s), 6.28 (4H, br s), 4.34 (1H, ddd, J=5.3, 7.5, 9.4 Hz), 4.08 (2H, q, J=7.1 Hz), 4.03 (2H, q, J=7.1 Hz), 3.07 (1H, dd, J=4.4, 16.6 Hz), 2.66-2.43 (5H, m), 2.40 (2H, t, J=7.4 Hz), 2.09-1.89 (3H, m), 1.83-1.73 (1H, m), 1.48-1.37 (1H, m), 1.17 (3H, t, J=7.1 Hz), 1.15 (3H, t, J=7.1 Hz)

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, 6312-72-7, 2,6-Diamino-5-bromopyrimidin-4(1H)-one.

Reference:
Patent; Agouron Pharmaceuticals, Inc.; US5726312; (1998); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 911461-47-7, 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 911461-47-7, name is 4,6-Dichloropyrimidine-5-carboxamide. This compound has unique chemical properties. The synthetic route is as follows.

4, 6-DICHLORO-PYRIMIDINE-5-CARBALDEHYDE (15.0 g, 84,75 mmol, 1.0 equivalent) was dissolved in ethyl acetate (150 mL), mixed with hydroxylamine hydrochloride in water (30ML) and added sodium acetate. Reaction was at left room temperature for 1.5 hours. Worked up with ethyl acetate, sodium bicarbonate, dried with magnesium sulfate, rotovaped and dried and high vacuum to afford a white solid (14.593 g). The white solid (iminohydroxy intermediate) was added to thionyl chloride (100 mL) at 0 C with stirring and allowed to warm to room temperature for 3 hours. The reaction was quenched in ice (500G), and the precipitated was filtered off, washed with cold water, and dried under high vacuum to afford a white solid as product (10. 739g, 72. 8%). 1H NMR 400MHZ CDC13 B (ppm): 8. 95 (s, LH, pyrimidine).

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 911461-47-7, 4,6-Dichloropyrimidine-5-carboxamide.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2005/7647; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia