Tag: M.W:100-200

Synthetic Route of 3680-69-1, 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.3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H4ClN3, molecular weight is 153.5691, as common compound, the synthetic route is as follows.

Preparation 109; 4-Chloro-5-iodo-7H-pyrrolo|”2.3-Patent; ELI LILLY AND COMPANY; WO2008/140947; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 944129-00-4, Adding some certain compound to certain chemical reactions, such as: 944129-00-4, name is Methyl 6-amino-2-chloropyrimidine-4-carboxylate,molecular formula is C6H6ClN3O2, 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 944129-00-4.

6-Amino-2-chloropyrimidine-4-carboxylic acid methyl ester (2.25 g, 12 mmol, 4-chloro-2-fluoro-3-methoxyphenylboronic acid (3.27 g, 16 mmol), and bis(triphenylphosphine)palladium(II) dichloride (842 mg, 1.2 mmol) were combined in 12 mL of 1,2-dimethoxyethane and 12 mL of water. The reaction mixture was heated at 80 C. for 2 h and the cooled reaction mixture was partitioned between ethyl acetate and water. The organic phase was washed with water, dried, and concentrated under vacuum. The product was purified by flash chromatography on silica gel to yield the title compound (2.0 g, 53.5% yield): mp 188-190 C.: 1H NMR (CDCl3) delta 7.66 (dd, 1H), 7.22 (dd, 1H), 7.14 (s, 1H), 5.25 (br s, 2H), 4.0 (s, 3H), 3.99 (s, 3H).

According to the analysis of related databases, 944129-00-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dow AgroSciences LLC; US2009/88322; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 55583-59-0, 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. 55583-59-0, name is 2,5-Diamino-4,6-dichloropyrimidine. A new synthetic method of this compound is introduced below.

In a reaction vessel, 4,6-dichloropyrimidine-2,5-diamine (358 mg, 2.00 mmol), 5′-m-terphenylboronic acid (1.22 g, 4.45 mmol), sodium carbonate (1.06 g) Add ethanol (5 mL) and distilled water (5 mL) to a solution of 10.0 mmol) and tetrakis (triphenylphosphine) palladium (0) (116 mg, 0.100 mmol) in toluene (20 mL) at After stirring for 20 hours under heating and reflux conditions under an argon atmosphere, the reaction solution was cooled to room temperature. Distilled water (5 mL) was added and stirred, and the separated aqueous layer was extracted three times with ethyl acetate (10 mL). Thereafter, the whole organic layer is combined, saturated aqueous sodium chloride solution (10 mL) is added thereto, the mixture is stirred and washed, anhydrous sodium sulfate is added to the separated organic layer for dehydration and the filtrate after filtration is concentrated under reduced pressure The The concentrate thus obtained is purified by flash column chromatography (silica gel, n-hexane / ethyl acetate),4,6-Di ([1,1 ‘: 3′, 1′-terphenyl] -5’-yl) pyrimidine-2,5-diamine(1.01 g, 90% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,55583-59-0, 2,5-Diamino-4,6-dichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Microbial Chemistry Research Foundation; Kumagai, Naoya; Noda, Hidetoshi; Asada, Yasuko; Shibazaki, Masakatsu; (48 pag.)JP2019/64981; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 2927-71-1, 2,4-Dichloro-5-fluoropyrimidine, 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, Formula: C4HCl2FN2, blongs to pyrimidines compound. Formula: C4HCl2FN2

A solution of 3-nitroaniline and 2,4-dichloro-5-fluoro-pyrimidine in MeOH was stirred for 2 hours at 70 C. The mixture was diluted with water and the resulting precipitate was filtered to give 2-chloro-N4-(3-nitrophenyl)-5-fluoro-2,4-pyrimidineamine as a pale brown solid. 1H NMR (DMSO): delta 10.34 (s, 1H), 8.73 (d, 1H, J=2.4 Hz), 7.66-8.29 (m, 4H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2927-71-1, 2,4-Dichloro-5-fluoropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; Singh, Rajinder; Argade, Ankush; Payan, Donald; Molineaux, Susan; Holland, Sacha; Clough, Jeffrey; Keim, Holger; Bhamidipati, Somasekhar; Sylvain, Catherine; Li, Hui; Rossi, Alexander; US2015/266828; (2015); 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.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.COA of Formula: C5H4Cl2N2

Example 7; Preparation of 7-(4-chlorophenyl)-5-methyl-8-(pyridin-4-yl)-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one; A. Preparation of 4-chloro-6-hydrazinyl-2-methylpyrimidine; To a stirred solution of 4,6-dichloro-2-methylpyrimidine (1.63 g, 10.0 mmol) in THF (25 mL) at room temperature under argon was added H2NNH2 (0.64 g, 20.0 mmol). The reaction mixture was stirred at room temperature under argon overnight. Analysis by HPLC/MS indicated that the reaction was complete. The solvent was evaporated, and the residue was coevaporated with toluene (2¡Á5 mL) then THF (5 mL), and then dried under vacuum. The crude title compound was used directly in the next step. HPLC/MS: retention time=0.77 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1780-26-3, 2-Methyl-4,6-dichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Wu, Gang; Mikkilineni, Amarendra B.; Sher, Philip M.; Murugesan, Natesan; Gu, Zhengxiang; US2006/287341; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 3680-69-1, 4-Chloro-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, 3680-69-1, blongs to pyrimidines compound. Formula: C6H4ClN3

Step C: 4-Chloro-7-{[2-(trimethylsilyl) ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine To a suspension of sodium hydride (36.141 g, 903.62 mmol) in N,N-dimethylacetamide (118 mL) at -5 C. (ice/salt bath) was added a dark solution of 4-chloropyrrolo[2,3-d]pyrimidine (119.37 g, 777.30 mmol) in N,N-dimethylacetamide (237 mL) slowly. The flask and addition funnel were rinsed with N,N-dimethylacetamide (30 mL). A large amount of gas was evolved immediately. The mixture became a slightly cloudy orange mixture. The mixture was stirred at 0 C. for 60 min to give a light brown turbid mixture. To the mixture was slowly added [2-(trimethylsilyl)ethoxy]methyl chloride (152.40 g, 914.11 mmol) and the reaction was stirred at 0 C. for 1 h. The reaction was quenched by addition of 12 mL of H2O slowly. More water (120 mL) was added followed by methyl tert-butyl ether (MTBE) (120 mL). The mixture was stirred for 10 min. The organic layer was separated. The aqueous layer was extracted with another portion of MTBE (120 mL). The organic extracts were combined, washed with brine (120 mL*2) and concentrated under reduced pressure to give the crude product 4-chloro-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine as a dark oil. Yield: 85.07 g (97%); LC-MS: 284.1 (M+H)+. It was carried to the next reaction without purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3680-69-1, its application will become more common.

Reference:
Patent; Incyte Corporation; Vaddi, Krishna; US2015/246046; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 22536-65-8, 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. 22536-65-8, name is 2-Chloro-5-methoxypyrimidine, molecular formula is C5H5ClN2O, 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.

General procedure: To a solution of 1.0 eq. of VII and 1.20 eq. of a 2-halopyrimidine in H20 and dioxane was added 2.0 eq. of potassium fluoride. The mixture was subjected to microwave irradiation maintaining a reaction temperature of 120 C for 1 h. The solvent was removed in vacuo, andthe residue was purified by chromatography.

According to the analysis of related databases, 22536-65-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARBUTUS BIOPHARMA CORPORATION; COLE, Andrew, G.; DORSEY, Bruce, D.; KAKARLA, Ramesh; KULTGEN, Steven; QUINTERO, Jorge; (353 pag.)WO2018/172852; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 874-14-6, 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. 874-14-6, name is 1,3-Dimethyluracil, molecular formula is C6H8N2O2, 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.

0.14 g (1.0 mmol) of 1,3-dimethyluracil was weighed and placed in a 50 ml two-neck flask equipped with a magnetic rotor and the atmosphere in the flask was replaced with argon. The following materials were added thereinto: 2.0 ml of a 1N dimethyl sulfoxide solution of sulfuric acid, 1.0 ml of a 3.0 mol/l dimethyl sulfoxide solution of trifluoromethyl iodide, 0.2 ml of a 30percent hydrogen peroxide aqueous solution and 0.3 ml of a 1.0 mol/l aqueous solution of ferric sulfate. The mixture was stirred at 40 to 50¡ãC for 20 minutes and then the resulting solution was cooled to room temperature. Formation of 1,3-dimethyl-5-trifluoromethyluracil (19F-NMR yield: 78percent) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard. 1,3-Dimethyl-5-trifluoromethyluracil was obtained as a white solid (0.12 g, yield: 44percent) by preparative thin-layer chromatography. 1H-NMR (deuterated acetone): delta3.25(s, 3H), 3.51(s, 3H), 8.23(q, JHF=1.05Hz, 1H). 13C-NMR (deuterated acetone): delta27.8, 37.6, 102.9(q, JCF=32.3Hz), 123. 8 (q, JCF=268.4Hz), 146.4 (q, JCF=5. 91Hz), 151.9, 159.5. 19F-NMR (deuterated acetone): delta-60.6. MS (m/z): 208[M]+.

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 874-14-6, 1,3-Dimethyluracil.

Reference:
Patent; Tosoh Corporation; Tosoh F- Tech Inc.; SAGAMI CHEMICAL RESEARCH CENTER; EP1947092; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 933702-55-7 ,Some common heterocyclic compound, 933702-55-7, molecular formula is C5H3ClN2O, 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.

Dissolve 2-chloropyrimidine5-carhaldehyde (0.5 g, 3.5 mmol) in chloroform (10 mL), add diethyiaminosuifur trioxide (567 mg, 3,5 mmoi), then reflux for 1 hour. Cool the mixture to ambient temperature and quench with 1-120. Separate the layers, wash the organic fraction with 1-120 (2x), dry over Mg504, filter, collect the filtrate, and concentrate the filtrate under reduced pressure to provide the title product (327 mg, 51%),

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. 933702-55-7, 2-Chloropyrimidine-5-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; ESCRIBANO, Ana Maria; GONZALEZ, Maria Rosario; LAFUENTE BLANCO, Celia; MARTIN-ORTEGA FINGER, Maria Dolores; WILEY, Michael R.; (82 pag.)WO2016/187384; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 10325-70-9, 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.10325-70-9, name is 5-Acetylpyrimidine, molecular formula is C6H6N2O, molecular weight is 122.1246, as common compound, the synthetic route is as follows.

Preparation 84 (R)-N-((5)-2-(2,4-difluorophenyl)-4-oxo-4-(pyrimidin-5-yl)butan-2-yl)-2-methylpropane- 2-sulfinamide To a solution of l-(pyrimidin-5-yl)ethanone (2.072 g, 16.97 mmol) in DMF (40 mL) was added 60 % wt aH (0.747 g, 18.66 mmol) at 0 C under nitrogen. The mixture was stirred at 0 C for 30 min. A solution of (R,¡ê)-N-(l-(2,4-difluorophenyl)ethylidene)-2- methylpropane-2-sulfinamide from preparation 73 (2.2 g, 8.48 mmol) in DMF (4 mL) was slowly added at -10 C under nitrogen. The mixture was stirred from -10 C to -5 C over 1.5 h. The reaction was quenched with water, and extracted with 2×250 mL of ethyl acetate. The combined organic layers were removed, dried over sodium sulfate, and concentrated. The residue was purified via silica gel chromatography (gradient elution using ethyl acetate to 10% methanol in ethyl acetate) to give (R)-N-((5)-2-(2,4- difluorophenyl)-4-oxo-4-(pyrimidin-5-yl)butan-2-yl)-2-methylpropane-2-sulfinamide (1.5 g, 3.93 mmol, 46.4 % yield). MS (M+H)+ = 382.05. 1H NMR (500MHz, CHLOROFORM-d) delta 9.37 (s, 1H), 9.18 (s, 2H), 7.61 (td, J=9.3, 6.5 Hz, 1H), 6.97 – 6.89 (m, 1H), 6.74 (ddd, J=12.9, 8.4, 2.6 Hz, 1H), 5.32 (s, 1H), 4.21 (dd, J=18.6, 1.4 Hz, 1H), 3.91 (dd, J=18.6, 2.9 Hz, 1H), 1.86 (s, 3H), 1.34 (s, 9H).

The chemical industry reduces the impact on the environment during synthesis 10325-70-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WU, Yong-Jin; GUERNON, Jason M.; WO2014/98831; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia