Pyrimidines

Electric Literature of 1780-26-3, 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.1780-26-3, name is 2-Methyl-4,6-dichloropyrimidine, molecular formula is C5H4Cl2N2, molecular weight is 163.0047, as common compound, the synthetic route is as follows.

To 12 ml of 1,4-dioxane, 0.75 g of phenylboronic acid, 1.67 g of potassium carbonate, 0.13 g of dichlorobis (triphenylphosphine) palladium and 1 g of 4,6- dichloro-2-methylpyrimidine were added. This mixture was stirred at 60C for 3 hours and then stirred at 800C for 6 hours. The reaction mixture was left standing to cool to room temperature, poured into an aqueous saturated ammonium chloride solution and then extracted three times with tert- butyl methyl ether. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography to obtain 0.64 g of 4-chloro-2-methyl- 6-phenylpyrimidine.4-chloro-2-methyl-6-rhohenylpyrimidine 1 H-NMR : 2 . 78 ( s , 3H ) , 7 . 49-7 . 56 (m, 4H ) , 8 . 04 -8 . 07 (m, 2H )

Statistics shows that 1780-26-3 is playing an increasingly important role. we look forward to future research findings about 2-Methyl-4,6-dichloropyrimidine.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; MIZUNO, Hajime; WO2010/134478; (2010); A1;,
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. 7752-72-9, name is 5-Chloro-6-methylpyrimidin-4(3H)-one. This compound has unique chemical properties. The synthetic route is as follows. name: 5-Chloro-6-methylpyrimidin-4(3H)-one

14.5g (0.1mol) 4- hydroxy-5-chloro-6-methylpyrimidine dissolved in 50ml of toluene, was added dropwise with stirring to the reaction flask 50ml phosphorus oxychloride, after dropwise addition the reaction heated at reflux for 5-7 hours, TLC monitored after completion of the reaction. Toluene was evaporated under reduced pressure and excess phosphorus oxychloride, with stirring the reaction was poured into ice water, the aqueous phase was extracted with ethyl acetate (3 × 50ml), the combined organic phase was dried over anhydrous magnesium sulfate, filtered, and dissolved. The residue was purified by column chromatography (eluent, ethyl acetate and petroleum ether (boiling range 60-90 deg. C), the volume ratio of 1: 4) was isolated as a yellow liquid 14.43g, yield 88.5%.

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, 7752-72-9, 5-Chloro-6-methylpyrimidin-4(3H)-one.

Reference:
Patent; Sinochem Agrochemicals R & D Co., Ltd.; Guan, Aiying; Yang, Fan; Wang, Junfeng; Chen, Wei; Fan, Xiaoxi; Wang, Xiuli; Chen, Xuanming; Li, Keke; Li, Zhinian; Liu, Zhangling; (73 pag.)CN105732585; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1224944-77-7 ,Some common heterocyclic compound, 1224944-77-7, molecular formula is C9H8ClN3O2, 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.

ompound 4 (2 g, 10.5 mmol) and Compound 7 (2.4 g, 10.5 mmol)Add to n-butanol (50 mL) in turn, then add diisopropylethylamine (10.8 g, 84 mmol).The temperature was raised to 120 C and stirred overnight, and TLC showed that the starting material disappeared.N-butanol is removed under reduced pressure,Water (50 mL) was added to the residue.Extracted with ethyl acetate (50 mL*3).The organic phases were combined and dried over anhydrous magnesium sulfate.Filtration, concentration, silica gel column chromatography (PE: EA = 1:1)Obtained a white solid 8 (3.1 g),The generation rate is 97%.

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. 1224944-77-7, Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhengzhou Taijihongnuo Pharmaceutical Co., Ltd.; Wu Yusheng; Zhi Wubin; Li Jingya; Wang Xin; Wu Shiyong; Liang Apeng; Guo Ruiyun; (31 pag.)CN109516999; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 3073-77-6, 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 3073-77-6, name is 2-Amino-5-nitropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 3. Synthesis of N-f4-(3-Pyrrolidin-l-vI-Propane-l-Sulfonvn-Phenvn- Pyrimidi?e-2,5-Diamine (Intermediate 2)[0127] To a solution of 2-amino-5-nitropyrimidine (840 mg, 6.0 mmol) in 50 mL anhydrous 1,4-dioxane were added l-[3-(4-bromo-benzenesulfonyI)-propyl]-pyrrolidine (2.9 g, 8.7 mmol), Xantphos, (690 mg, 1.2 mmol), Pd2(dba)3 (559 mg, 0.61 mmol) and CS2CO3 (5.8 g, 18 mmol). The reaction mixture was stirred at 1000C for 5 h under argon. The solvent was removed under reduced pressure. The resulting solution was extracted with CHCI3 (3 x 50 mL) and sat. NaHCO3 (50 mL). The organic layer was separated, washed with brine, dried over Na2SO4 and filtered. The organic solvent was removed and the crude product was purified by silica gel column with 20% CH3OH / CHCl3 as an eluent. The precipitated yellow solid was isolated by washed with acetone and dried in vacuo (1.2 g, 52%). The above product was hydrogenated in 100 mL methanol/ethyl acetate (v/v: 1:1) using Pd/C (10%, 1 g) for 2 h. The palladium catalyst was removed by filtration, and the solvent was evaporated. The pale yellow solid was isolated by washed with acetone/methanol (v/v 5:1) and dried in vacuo (550 mg, 49%).[0128] 1H NMR (DMSOd6): delta 1.60-1.68 (m, 6H), 2.10-2.35 (m, 4H), 2.40-2.50 (m, 2H), 3.05-3.25 (m, 2H)5 5.02 (br s, 2H), 7.68 (d, J= 9.0 Hz, 2H), 7.87 (d, J= 9.0 Hz, IH)5 8.02 (s, 2H), 9.68 (s, IH).

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 3073-77-6, 2-Amino-5-nitropyrimidine.

Reference:
Patent; TARGEGEN, INC.; WO2008/8234; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 32779-36-5, 5-Bromo-2-chloropyrimidine, 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, 32779-36-5, blongs to pyrimidines compound. SDS of cas: 32779-36-5

A mixture of 5-bromo-2-chloropyrimidine (1 g, 5.18 mmol), dimethylamine hydrochloride (1.26 g, 15.6 mmol) and K2C03 (2.16 g, 15.6 mmol) in EtOH (15 mL) was heated to 120C for 16h. After cooling, the solvent was evaporated off and the residue was used for next step without further purification. LCMS (m/z): 202.1/203.1 [M+H]”7 [M+2H]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,32779-36-5, its application will become more common.

Reference:
Patent; EPIZYME, INC.; DUNCAN, Kenneth, W.; CHESWORTH, Richard; MUNCHHOF, Michael, John; JIN, Lei; WO2014/100695; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1436686-17-7 ,Some common heterocyclic compound, 1436686-17-7, molecular formula is C9H8BrN3O2, 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 0.28 g (1 .14 mmol) of compound 1-2 in 1.5 mL of EtOH were added 0.31 g (1 .14 mmol) of compound 2-2 and 0.026 g (0.23 mmol) of TFA at room temperature. The mixture in a sealed tube was stirred at 90 C overnight under N2atmosphere and cooled to rt. It was diluted with 10 mL of ethyl acetate and 50 mL of water, and extracted with three 50 mL portions of ethyl acetate. The combined organic extracts were washed with brine, and dried over anhydrous Na2S04. After filtration, the filtrate was concentrated to afford a residue, which was purified by chromatography on silica gel column eluted with 50% of ethyl acetate in petroleum ether to afford compound 1-3. LC-MS: m/e = 435 [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,1436686-17-7, its application will become more common.

Reference:
Patent; ANGEX PHARMACEUTICAL, INC.; WU, Wen-Lian; YANG, Zhiqiang; LEE, Francis; TAN, John Qiang; (112 pag.)WO2019/94143; (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.5177-27-5, name is 5-Amino-2,4-dichloropyrimidine, molecular formula is C4H3Cl2N3, molecular weight is 163.9927, as common compound, the synthetic route is as follows.SDS of cas: 5177-27-5

To a mixture containing 2,4-dichloropyrimidin-5-amine (900 mg, 5 5 mmol), 4- ethynyl-l,2~dimethoxy benzene (980 mg, 6.0 mmol), copper(I) iodide (105 mg, 0 55 mmol) and Pd(Ph3P)4 (190 mg, 0 17 mmol) in a screw cap vial was added nitrogen gas purged TEA (15 mL). The vial was fitted with a Teflon lined septum cap. The system was evacuated under vacuum (via a needle from a mtrogen/vacuum manifold line) and backfilled with nitrogen gas. The needle was removed and the vial was heated at 100 C for 3 h. The reaction mixture was cooled to room temperature and concentrated. The resulting slurry was dissolved in THF/DCM/MeOH mixture and adsorbed to 10 g silica and transferred to an empty cartridge. The cartridge was fitted to a Teledyne ISCO CombiFlash Rf chromatography system and purified on a 24 g ISCO silica gel column which was eluted over a 15 min gradient with 5%-100% hexanes/EtOAc to afford 2- chloro-4-((3,4-dimethoxyphenyl)ethynyl)pyrimidin-5-amine (1.3 g, 4.5 mmol, 82 % yield), MS m/z (290, M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5177-27-5, 5-Amino-2,4-dichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DYCKMAN, Alaric J.; DODD, Dharmpal S.; MUSSARI, Christopher P.; WHITELEY, Brian K.; KUMAR, Sreekantha Ratna; RAMACHANDRA REDDY, Anupama Kandhi; (134 pag.)WO2019/126083; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 51940-64-8, 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. 51940-64-8, name is Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate, molecular formula is C7H6Cl2N2O2, 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.

A solution of 2,4-dichloropyrimidine-5-carbonyl chloride (1.00 g, 4.76 mmol) in ethanol (6.0 mL) was added DIPEA (2.5 raL, 14,4 mmol) slowly at 0 C under nitrogen. After 30 mm, hex-5-yn-1-amine (0.476 g, 4.91 mmol) was added in one portion. The reaction mixture was stirred at room temperature for 3.5 h, then was added dropwise to a solution of 6-azidohexan-1-amine (0.801 g, 5.64 mmol) in ethanol (4.0 mL) at 50 C After the reaction was complete (monitored by LCMS), the mixture was diluted with water (10 mL) and concentrated under a reduced pressure and filtered. The yellow solid was washed with water and dried under vacuum to be used in the next step without further purification (0.723 g, 39% over 3 steps).

According to the analysis of related databases, 51940-64-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; WANG, Xiaodong; ZHANG, Weihe; KIREEV, Dmitri; LIU, Jing; MCIVER, Andrew Louis; WO2014/85225; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 4983-28-2, 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. 4983-28-2, name is 2-Chloro-5-hydroxypyrimidine, molecular formula is C4H3ClN2O, 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.

b) 7.2 g (59 mmol) R-2,2-difluoro-cyclopropanecarboxylic acid are added to 100 mL THF, chilled to 0°C and 35 mL (77 mmol) lithium aluminum hydride solution (2.2 M in 2-methyltetrahydrofuran) are added dropwise. The mixture is stirred at r.t. over night. After that the mixture is chilled to 0°C and quenched by the addition of 3 ml water and 3 ml aq. NaOH solution (c= 4 mol/L) slowly. The resulting mixture is stirred for 30 min, filtered, washed with THF and the filtrate is concentrated by evaporation. The residue is added to Et2O, dried over Na2SO4, filtered and the solvent is removed in vacuo. C4H4F2O(M= 108.1 g/mol) Rt (GC):15.4 min (method a) c) ) 2.16 g (20.0 mmol) of the above mentioned product, 2.75 g (20 mmol) 1-chloro-5- hydroxypyrimidine and 6.56 g (25 mmol) triphenylphosphine are added to 20 ml THF and cooled to 0 °C. Then 11.5 mL (25 mmol) diethylazocarboxylate (40 percent in toluene) are added carefully at constant temperature. Then cooling is removed and the mixture is stirred at r.t. for 3 h. Afterwards the solvent is removed in vacuo, diethylether is added and the mixture is filtered. The solvent is removed in vacuo and the residue is purified by flash chromatography (silica gel, PE/EtOAc) C8H7CIF2N2O (M= 220.60 g/mol) ESI-MS: 221 [M+Hf Rt (HPLC): 0.91 min (method I)

According to the analysis of related databases, 4983-28-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FLECK, Martin; HEIMANN, Annekatrin; HEINE, Niklas; NOSSE, Bernd; ROTH, Gerald Juergen; WO2014/170197; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 17321-93-6 ,Some common heterocyclic compound, 17321-93-6, molecular formula is C5H6BrN3, 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.

[0244] To a dry 1 L flask was added 5-bromo-4-methylpyrimidine-2~ylamine(18.8 g, 100 mmol), potassium acetate (29.45 g, 300 mmol), 4,4,5,5-tetramethyl-2- (4,4,5 ,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l,3,2-dioxaborolane (26.7 g, 105 mmol) and dioxane (500 mL). Argon was bubbled through the solution for 15 minutes, at which time l,r-bis(diphenylphosphino)ferrocene palladium(II) chloride dichloromethane adduct (4.07 g, 5 mmol) was added. The reaction was refluxed in a 115 0C oil bath for 18 hours under argon. After cooling to room temperature, EtOAc (500 mL) was added and the resulting slurry was sonicated and filtered. Additional EtOAc (500 mL) was used to wash the solid. The combined organic extracts were washed with H2O (2×300 mL), NaCl(sat.) (30O mL), dried over Na2SO4, concentrated and purified by SiO2 chromatography (EtOAc eluent) yielding 18.1 g of an off-white solid. By 1H NMR the material was a 5:1 mixture of boronate ester and 4-methylpyrimidine-2-ylamine as a 7 001708byproduct. The material was used as is in subsequent Suzuki reactions. LCMS {m/z): 154 (MH+ of boronic acid, deriving from in situ product hydrolysis on LC). 1H NMR (CDCl3): delta 8.52 (s, IH), 5.14 (bs, 2H), 2.56 (d, 3H), 1.32 (s, 12H).

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. 17321-93-6, 2-Amino-5-bromo-4-methylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; WO2007/84786; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia