Tag: M.W:100-200

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. 23956-12-9, name is 5-(2-Hydroxyethyl)pyrimidine-2,4(1H,3H)-dione. A new synthetic method of this compound is introduced below., Formula: C6H8N2O3

On the basis of the modification of the 5-position of the uracil. The preparation of hydroxyethyluracil 28 is possible on a large scale according to a known method (J. D. Fissekis, A. Myles, G. B. Brown, J. Org. Chem. 1964, 29, 2670. g-Butyrolactone 25 was formylated with methyl formate, the sodium salt 26 was reacted to give the urea derivative 27 and this was cyclized to the hydroxyethyluracil 28 (Scheme 1). [C00006] [C00007] [00083] Hydroxyethyluracil 28 was methylated with methanesulphonyl chloride in pyridine to give 29 (J. D. Fissekis, F. Sweet, J. Org. Chem. 1973, 38, 264). [00084] The following stages have been newly invented: using sodium azide in DMF, 29 was reacted to give the azide 30 and this was reduced with triphenylphosphine in pyridine to give the aminoethyluracil 31. The amino function in 31 was finally protected with N-ethoxycarbonylphtalimide (Scheme 2). Nucleosidation of ribose tetrabenzoate 33 with N-phtaloylaminoethyluracil 32 produced the ribose tribenzoate 34 in good yields. The anomeric centre of the pyranose ring is in the beta configuration, as can be clearly seen from the coupling constants between H-C(1′) and H-C(2′) of J=9.5 Hz. Subsequent removal of the benzoate protective groups using NaOMe in MeOH yielded the linker triol 35. 35 was reacted with benzoyl chloride at -78 C. in pyridine/dichlormethane 1:10 in the presence of DMAP. In this process, in addition to the desired 2′-benzoate 36 (64%), 2′,4′-dibenzoylated product (22%) was also obtained, which was collected and converted into the triol 35 analogously to the methanolysis of 34 to 35. The 2′-benzoate 36 was tritylated with dimethoxytrityl chloride in the 4′-position in yields of greater than 90% in the presence of Huenig’s base in dichloromethane. The rearrangement of 4′-DMT-2′-benzoate 37 to the 4′-DMT-3′-benzoate 38 was carried out in the presence of DMAP, p-nitrophenol and Huenig’s base in n-propanol/pyridine 5:2. After chromatography, 38 is obtained. 4′-DMT-3′-benzoate 38 was finally reacted with ClP (OAll)N(iPr)2 to give the phosphoramidite 39 in the presence of Hunig’s base (Scheme 3). This can be employed for the automated oligonucleotide synthesis without alteration of the synthesis protocols.

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, 23956-12-9, 5-(2-Hydroxyethyl)pyrimidine-2,4(1H,3H)-dione.

Reference:
Patent; Nanogen Recognomics GmbH; US6699978; (2004); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 271-70-5, Adding some certain compound to certain chemical reactions, such as: 271-70-5, name is 7H-Pyrrolo[2,3-d]pyrimidine,molecular formula is C6H5N3, 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 271-70-5.

5-Bromo-7H-pyrrolo[2,3-d]pyrimidine (7) is prepared by dissolving 7H-pyrrolo[2,3-d]pyrimidine (6) in chloroform and slowly adding Br2 in carbon tetrachloride at 0 C. After stirring for 1-2 hours, the reaction may be quenched in aqueous hydrochloric acid. Isolation by conventional means (e.g. extraction and silica gel chromatography) provides compound 7.

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. 271-70-5, 7H-Pyrrolo[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ibrahim, Prabha N.; Bremer, Ryan; Zhang, Jiazhong; Nespi, Marika; Cho, Hanna; US2009/286782; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 54660-78-5 ,Some common heterocyclic compound, 54660-78-5, molecular formula is C4H4ClN3, 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.

General procedure: In a sealed tube and under argon atmosphere, the appropriate diazine (1.0equiv) and the corresponding boronic ester (3.0equiv) were dissolved in a mixture of dioxane/water 12:1 (7.7mL/mmol of diazine), then K3PO4 (3.0 or 5.0equiv) and palladium catalyst (Pd(PPh3)4 8molpercent or Pd(OAc)2 5molpercent+S-Phos 10molpercent) were added. The reaction mixture was refluxed overnight and then cooled to room temperature. The crude product was evaporated to dryness and purified using column chromatography or precipitated in MeOH/water (2:1) (20mL/mmol of diazine).

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. 54660-78-5, 4-Chloropyrimidin-5-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Fresneau, Nathalie; Cailly, Thomas; Fabis, Fre?de?ric; Bouillon, Jean-Philippe; Tetrahedron; vol. 69; 26; (2013); p. 5393 – 5400;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 99469-85-9, 4,5-Dichloro-2-(methylthio)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, Safety of 4,5-Dichloro-2-(methylthio)pyrimidine, blongs to pyrimidines compound. Safety of 4,5-Dichloro-2-(methylthio)pyrimidine

Compound 51. To a mixture of compound 49 (976 mg, 5.13 mmol, 2 eq.), compound 50 (0.5 g, 2.56 mmol, 1 eq.) , Pd(PPh3)2Cl2 (360 mg, 512 mumol, 0.2 eq.), and CuI (244 mg, 1.28 mmol, 0.5 eq.) in THF (10 mL) was added TBAF (1 M, 2.56 mL, 1 eq.) in one portion at 0 C under N2. The reaction mixture was stirred at 60 C under N2 for 10 h. The mixture was partitioned between H2O(100 mL) and EtOAc(200 mL). The combined organic phase were washed with brine (200 mL), dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, PE/EtOAc: 1/0 to 50 /1) and prep- TLC (PE/EtOAc: 20:1) to afford compound 51 (0.3 g, 1.26 mmol, 49% yield) as a brown oil. 1H NMR (CDCl3, 400 MHz) delta 8.47 (s, 1H), 2.61 (d, J = 5.9 Hz, 2H), 2.56 (s, 3H), 1.13-1.03 (m, 1H), 0.61-0.52 (m, 2H), 0.36 (q, J = 4.9 Hz, 2H).

The synthetic route of 99469-85-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM LTD.; SNIR-ALKALAY, Irit; VACCA, Joseph; BEN-NERIAH, Yinon; (238 pag.)WO2019/155468; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 20781-06-0, 2,4-Diaminopyrimidine-5-carboxaldehyde, 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: C5H6N4O, blongs to pyrimidines compound. Formula: C5H6N4O

General procedure: Appropriate substituted benzoyl hydrazine 4 (1 equiv) was added to a solution of intermediate 2 (1mmol) in ethanol (10mL). The reaction mixture was stirred for 3h at reflux under the condition of the presence of acetic acid as catalyzer, then poured into cold water and the resulting solid was collected by filtrated, washed with EtOH (10mL), and dried in the atmospheric pressure to give the desired title compounds A, B, and C.

The synthetic route of 20781-06-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; He, Haifeng; Xia, Hongying; Xia, Qin; Ren, Yanliang; He, Hongwu; Bioorganic and Medicinal Chemistry; vol. 25; 20; (2017); p. 5652 – 5661;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 4316-97-6, 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.4316-97-6, name is 4,6-Dichloro-5-methylpyrimidine, molecular formula is C5H4Cl2N2, molecular weight is 163.01, as common compound, the synthetic route is as follows.

1-Methyl-1 ,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole bis-hydrochloride salt (2.00 g,10.2 mmol) and 4,6-dichloro-5-methylpyrimidine (1.66 g, 10.2 mmol) were suspended tetrahydrofuran (51 ml.) at room temperature. To this was added triethylamine (4.41 ml_, 31.6 mmol), which caused cloudiness in the mixture and led to a brown solid sticking to the flask walls. This mixture was stirred at room temperature for 4 hours and then heated 50 degrees Celsius for an additional 19 hours. The reaction mixture was cooled to room temperature and diluted with water (100 ml_). This mixture was extracted with ethyl acetate (3 x 100 ml_). The organic extracts were pooled, washed with brine, dried over sodium sulfate, and filtered. The filtrate was reduced to dryness under vacuum to yield the title compound as a light brown solid (1 .95 g, 78%), which was used in the next step without further purification.1 H NMR (500 MHz, deuterochloroform) delta 2.54 (s, 3 H) 3.88 (s, 3 H) 4.90 (app. d, J=3.66 Hz, 4 H) 7.28 (s, 1 H) 8.29 (s, 1 H).

The chemical industry reduces the impact on the environment during synthesis 4316-97-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PFIZER INC.; MASCITTI, Vincent; MCCLURE, Kim Francis; MUNCHHOF, Michael John; ROBINSON, Ralph Pelton, Jr.; WO2012/69948; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 347418-42-2 ,Some common heterocyclic compound, 347418-42-2, molecular formula is C4H2ClFN2, 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.

A mixture of N-(5-(4-acetylpiperazin- l-yl)pyridin-2-yl)-2-(4-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)acetamide 196-1 (30 mg, 0.065 mmol), 4-chloro-5- fluoropyrimidine 196-2 (28 mg, 0.21 mmol) Pd(PPh3)4 (12 mg, 0.01 mmol) and K3PO4 (90 mg, 0.424 mmol) in dioaxane (0.6 mL) was flushed with nitrogen and heated to 110C for 2 hours. The salt was removed by filtration and the filtrate was taken to dryness by rotary evaporation. The residue was purified by reverse phase HPLC to give N-(5-(4-acetylpiperazin-l-yl)pyridin-2- yl)-2-(4-(5-fluoropyrimidin-4-yl)phenyl)acetamide 196. MS m/z 435.10 (M + 1). 1H NMR 400 MHz (DMSO-d6) deltaltheta.54 (s, IH), 9.06 (d, IH), 8.90 (d, IH), 7.98 (m, 3H), 7.86 (d, IH), 7.49 (d, 2H), 7.37 (m, IH), 3.73 (s, 2H), 3.50 (m, 4H), 3.09 (t, 2H), 3.02 (t, 2H), 1.97 (s, 3H).

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. 347418-42-2, 4-Chloro-5-fluoropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; IRM LLC; CHENG, Dai; ZHANG, Guobao; HAN, Dong; GAO, Wenqi; PAN, Shifeng; WO2010/101849; (2010); 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.56621-90-0, name is 5-Amino-2-chloropyrimidine, molecular formula is C4H4ClN3, molecular weight is 129.5477, as common compound, the synthetic route is as follows.Quality Control of 5-Amino-2-chloropyrimidine

To a solution of triphosgene (1.38 g, 4.65 mmol) in Ethyl acetate (20 ml) at 0 C. a solution of 2-chloro-5-aminopyrimidine (1 g, 7.75 mmol)/DIPEA (8 ml, 4.65 mmol) in ethyl acetate (40 ml) was slowly added (20 minutes) and the reaction mixture was stirred for 15 minutes at the same temperature. Maintaining the reaction mixture at 0 C., vacuum was applied (10 minutes) for removing the excess of phosgene. A solution of DMAP (0.945 g, 7.75 mmol) in ethyl acetate/dichloromethane 1:1 (8 ml) was added and the reaction mixture was stirred for 5 minutes at the same temperature. A solution of methyl (R)-2-amino-2-methyl-butyrate hydrochloride (2.59 g, 15.5 mmol) in ethyl acetate (30 ml) was slowly added (15 minutes) at 0 C. and the reaction mixture was stirred for 30 minutes at the same temperature. The reaction was quenched with aqueous buffer (pH3) while the pH was allowed to reach 5-6 and two phases were separated. The organic layer was washed with aqueous buffer (pH3) (2×20 ml) and then brine (20 ml), dried (Na2SO4), filtered and evaporated affording the urea intermediate as orange foam. The urea was dissolved in MeOH (20 ml), NaOMe (0.41 g, 7.75 mmol) was added and the reaction mixture was stirred for 15 minutes at r.t. The mixture was quenched with an aqueous saturated solution of ammonium chloride (25 ml) and diluted with ethyl acetate (50 ml). Two phases were separated and the organic layer was washed with brine (2×20 ml), dried (Na2SO4), filtered and evaporated. The residue was triturated with Et2O (10 ml) and the solid collected affording the title compound (1.22 g) as a beige solid. LC/MS: QC-3_MIN: Rt=1.341 min; 255 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,56621-90-0, 5-Amino-2-chloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Alvaro, Giuseppe; Marasco, Agostino; US2014/323508; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 22536-65-8, 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 22536-65-8, name is 2-Chloro-5-methoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Example 72 N-[1-(5-methoxypyrimidin-2-yl)piperidin-4-yl]-6-[5-(methylsulfonyl)-2,3-dihydro-1H-indol-1-yl]-N-(trifluoromethyl)pyrimidin-4-amine; [Show Image] 6-[5-(Methylsulfonyl)-2,3-dihydro-1H-indol-1-yl]-N-(piperidin-4-yl)-N-(trifluoromethyl)pyrimidin-4-amine (100 mg, 0.227 mmol) obtained in Reference Example 34 and 2-chloro-5-methoxypyrimidine (131 mg, 0.906 mmol) were dissolved in NMP (5.0 mL). Cesium carbonate (295 mg, 0.906 mmol) was added thereto, and the mixture was stirred at 80°C for 74 hr. After cooling to room temperature, the mixture was diluted with ethyl acetate, and water was added thereto. The organic layer was washed with water and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=6:4 (volume ratio)–>hexane:ethyl acetate=2:8 (volume ratio)], and the obtained solid was suspended in diisopropyl ether. The precipitate was collected by filtration, washed with diisopropyl ether and dried under reduced pressure to give the title compound (17.8 mg, yield 14percent) as a white solid. 1H-NMR (300 MHz, CDC13) delta:1.90 – 2.03 (m, 2 H), 2.04 – 2.24 (m, 2 H), 2.93 (t, J=12.7 Hz, 2 H), 3.04 (s, 3 H), 3.32 (t, J=8.7 Hz, 2 H), 3.81 (s, 3 H), 4.12 (t, J=8.9 Hz, 2 H), 4.69 – 4.88 (m, 3 H), 6.24 – 6.31 (m, 1 H), 7.73 (d, J=1.1 Hz, 1 H), 7.80 (dd, J=8.7, 1.9 Hz, 1H), 8.10 (s, 2 H), 8.56 (d, J=8.7 Hz, 1 H), 8.62 (d, J=1.1 Hz, 1 H).

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; Takeda Pharmaceutical Company Limited; EP2399914; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 90213-66-4, 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. 90213-66-4, name is 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H3Cl2N3, 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.

Example 2 (1 g, 5.318 mmol) and powdered KOH (446 mg, 7.978 mmol) was dissolved in 4 mL anhydrous DMSO. After 1 h at RT, the reaction mixture was quenched with water and the aqueous layer was extracted with EtOAc (2x).The organics were combined, dried (MgSO4), filtered and the volatiles were removed in vacuo. The residue was purified by flash chromatography (Sitheta2, hexanes/EtOAc, 2:1 ) to provide the desired product (892 mg, 83%) as a colourless solid. 1H NMR (CZ6-DMSO) delta 7.76 (1 H, d, J = 3.6 Hz), 6.70 (1 H, d, J= 3.6 Hz), 3.82 (3H, s).

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 90213-66-4, 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; VERNALIS (R & D) LTD.; WO2009/37467; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia