Tag: M.W:100-200

3934-20-1, 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 3934-20-1 as follows.

A solution of 2,4-dichloropyrimidine (0.500g, 3.36mmol) and N,N-diisopropylethylamine (0.818mL, 4.70mmol) in isopropanol (5mL) was stirred at 0C. Morpholine (0.319mL, 3.69mmol) was added dropwise and the solution continued to stir at 0C for 30min, and then room temperature for 12h. The reaction mixture was concentrated under reduced pressure and then partitioned between ethyl acetate and water. The organic layer was extracted three times, washed with brine, dried over sodium sulfate, and concentrated to dryness. The products were purified by silica column chromatography in hexanes and ethyl acetate to afford 4-(4-chloropyrimidin-2-yl)morpholine and 4-(2-chloropyrimidin-4-yl)morpholine in 7% and 92% yields, respectively. (0058) 4-(4-chloropyrimidin-2-yl)morpholine (15). (White solid, Yield: 7%). 1H NMR (500MHz, CDCl3) delta ppm 3.74 (m, 4H), 3.81 (m, 4H), 6.53 (d, J=4.9Hz, 1H), 8.16 (d, J=4.9Hz, 1H). LCMS found 200.0, [M+H]+. (0059) 4-(2-chloropyrimidin-4-yl)morpholine (16). (White solid, Yield: 92%). 1H NMR (500MHz, CDCl3) delta ppm 3.64 (br. s, 4H), 3.77 (m, 4H), 6.38 (d, J=5.9Hz, 1H), 8.07 (d, J=6.3Hz, 1H). LCMS found 200.0, [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 3934-20-1, I believe this compound will play a more active role in future production and life.

Reference:
Article; Woodring, Jennifer L.; Bachovchin, Kelly A.; Brady, Kimberly G.; Gallerstein, Mitchell F.; Erath, Jessey; Tanghe, Scott; Leed, Susan E.; Rodriguez, Ana; Mensa-Wilmot, Kojo; Sciotti, Richard J.; Pollastri, Michael P.; European Journal of Medicinal Chemistry; vol. 141; (2017); p. 446 – 459;,
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. 32779-36-5

To a solution of 5-bromo-2-chloro-pyrimidine (0.5 g, 2.58 mmol) in 1,4-dioxane (20 mL),tert-butyl piperazine-1-carboxylate (0.722 g, 3.88 mmol) and K2C03 (0.713 g, 5.17 mmol)were added at RT. The reaction mixture was refluxed for 4 h (TLC indicated complete consumption of starting material). The reaction mixture was brought toRT, diluted withwater (20 mL) and extracted with EtOAc (3 x 50 mL). The combined organic extracts werewashed with water (2 x 40 mL), brine (1 x 40 mL), dried over Na2S04 and concentratedunder reduced pressure to give the residue. The residue was further purified by columnchromatography (100-200 silica gel, 15 g, 10% EtOAc-Hexane) to afford tert-butyl4-(5-bromopyrimidin-2-yl)piperazine-l-carboxylate (0.7 g, 78%) as a white solid.1H NMR [400 MHz, CDCh]: J 8.29 (s, 2H), 3.75 (t, J = 4.8 Hz, 4H), 3.47 (t, J = 5.2 Hz,4H), 1.47 (s, 9H).LCMS: m/z: 287.44 [M-tBut.

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; MITOBRIDGE, INC.; TAKAHASHI, Taisuke; KLUGE, Arthur; LAGU, Bharat; JI, Nan; (162 pag.)WO2018/125961; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

611-08-5 , The common heterocyclic compound, 611-08-5, name is 5-Nitrouracil, molecular formula is C4H3N3O4, 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 suspension of 5-nitrouracil (10 g, 63 mmol) in POCl3 (100 mL) was refluxed for 5 h in the presence of N,N-dimethylaniline (10 mL), cooled to room temperature and poured on to crushed ice with vigorous stirring. The aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over MgSO4 and the solvent was evaporated under reduce pressure. The residue was purified by chromatography on silica gel (hexane/ethyl acetate; 1/1; v/v) to give the desired 2,4-dichloro-5-nitropyrimidine. LCMS: ret. time: 23.26 min.; purity: 95percent; 1H NMR (CDCl3): delta 9.16 (1H, s).

According to the analysis of related databases, 611-08-5, the application of this compound in the production field has become more and more popular.

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

3680-71-5 , The common heterocyclic compound, 3680-71-5, name is 1,7-Dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one, molecular formula is C6H5N3O, 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.

18D. 4-Chloro-7H-pyrrolor2,3-d]pyrimidine; To 7W-pyrrolo[2,3-cfjpyrimidin-4-ol (0.425 g, 3.14 mmol) was added phosphorus oxychloride (4 ml). The mixture was heated at reflux for 90 minutes and then cooled to room temperature. The solution was poured onto cracked ice, and extracted with chloroform (3 x 50 ml) and ethyl acetate (100 ml). The extracts were then dried and concentrated, and the residue obtained triturated with hot ethyl acetate (200 ml) to yield the desired product (0.204 g, 42percent).

According to the analysis of related databases, 3680-71-5, 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; WO2007/125315; (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. 74-69-1, name is 2-Methyl-4-pyrimidinamine. This compound has unique chemical properties. The synthetic route is as follows. 74-69-1

[00119] t-BuOK (1.00 M in THF, 84 mL, 84 mmol) was added to a stirring mixture of 2-bromo-4 chloropyridine (14.0 g, 72.7 mmol), 2-methylpyrimidin-4-amine (6.1 g, 55.9 mmol), Pd(dppf)C12 (0.82 g, 1.12 mmol), and dppf (2.48 g, 4.47 mmol) in toluene (204 mL). The reaction mixture was allowed to stir at 110 C for 16 h under a nitrogen atmosphere, then was allowed to cool to rt and concentrated. The crude compound was purified by column chromatography to provide N-(4-chloropyridin-2-yl)-2- methylpyrimidin-4-amine (10 g, 8 1%). LCMS (FA): m/z = 221.0 (M+H).

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, 74-69-1, 2-Methyl-4-pyrimidinamine.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; BHARATHAN, Indu T.; BLACKBURN, Chris; CIAVARRI, Jeffrey P.; CHOUITAR, Jouhara; CULLIS, Courtney A.; D’AMORE, Natalie; FLEMING, Paul E.; GIGSTAD, Kenneth M.; GIPSON, Krista E.; GIRARD, Mario; HU, Yongbo; LEE, Janice; LI, Gang; REZAEI, Mansoureh; SINTCHAK, Michael D.; SOUCY, Francois; STROUD, Stephen G.; VOS, Tricia J.; XU, He; YE, Yingchun; WO2015/108881; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

5750-76-5 , The common heterocyclic compound, 5750-76-5, name is 2,4,5-Trichloropyrimidine, molecular formula is C4HCl3N2, 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.

[00369] 245-trichloropyrimidine (54.2 g, 0296 mol, 1.0 eq.), (2arninophenyl)dimethyl..phosphine oxide (50.Og, 0.296 mole, 1.0 eq.), potassium carbonate (49.lg, 0355 mol, 1.2 eq.) and tetrabutylammonium bisuifate (10.2 g. 0.03 mole, 0.1 eq.) were combined in DMF (1050 mL), and heated at 65 C for -8.0-8.5 h. During the course of heating, an offwhite suspension formed. Upon coong, the mixture was cooled to rt and filtered. The coHected solids were rinsed with DMF (2 x 50 mL), and the combined filtrates were concentrated in vacuo. The resulting residue was dissolved in EtOAc (1 .3 L) and water (350 mL). The aqueous layer was isolated and extracted with EtOAc (2 x 250 mL). The combined organic layers were washed with brine (20% w/w, 500 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to afford (2..((25dichloropyriniidin4 yl)amino)phenyl)dimethylphosphine oxide as an offwhite solid.

According to the analysis of related databases, 5750-76-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; ROZAMUS, Leonard, W.; SHARMA, Pradeep; (190 pag.)WO2016/65028; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

90213-66-4, Adding some certain compound to certain chemical reactions, such as: 90213-66-4, name is 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine,molecular formula is C6H3Cl2N3, 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 90213-66-4.

Zinc powder (8700 ¡¤ 0g, 133piomicron1, 10 ¡¤ Oeq ?) was added portionwise to glacial acetic acid (3 ¡¤ 3L, 53 ¡¤ 2mo1.4 ¡¤ Oeq ¡¤) and acetonitrile (30 ¡¤ 0L) mixture was added to complete the reaction temperature was raised to 80 C for 14 hours, the reaction was complete by TLC.87] The reaction mixture was cooled to 25 C, suction filtration, the filtrate was concentrated under reduced pressure and added to 30L of ice water, precipitated a large number of pink solid, filtration, the filter cake washed with water (5L X 3), dried to give a white solid 1501.7g. Yield: 73.54%.

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 90213-66-4.

Reference:
Patent; Nanjing Furunkaide Bio-pharmaceutical Co., Ltd.; Rong Liang; Li Jin; Li Hui; Jie Yuanping; Wu Xihan; Yang Minmin; (12 pag.)CN105949196; (2016); A;,
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. 32779-36-5, name is 5-Bromo-2-chloropyrimidine. A new synthetic method of this compound is introduced below., 32779-36-5

Step 1: 1-(5-Bromopyrimidin-2-yl)piperidin-4-olA mixture of 5-bromo-2-chloropyrimidine (5 g, 25.8 mmol), piperidin-4-ol (2.88 g, 28.4 mmol) and triethylamine (5.40 mL, 38.8 mmol) in EtOH (51.7 mL) was heated at 90¡ã C. for 0.5 h. The solvent was evaporated, the residue was diluted with 1N HCl (20 mL) and extracted with EtOAc (3.x.15 mL). The combined organic fractions were dried over Na2SO4 and the solvent was evaporated. The product was recrystallized from CH2Cl2/hexanes, filtered and washed with hexanes to afford the title product.1H NMR (500 MHz, acetone-d6): delta 8.36 (s, 2H), 4.29 (dt, 2H), 3.94-3.87 (m, 1H), 3.38 (ddd, 2H), 1.91-1.85 (m, 2H), 1.51-1.42 (m, 2H) ppm. MS: m/z 258, 260 (MH+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,32779-36-5, 5-Bromo-2-chloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Leblanc, Yves; Powell, David; Ramtohul, Yeeman K.; Leger, Serge; US2008/182838; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

1193-24-4, 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. 1193-24-4, name is 4,6-Dihydroxypyrimidine, molecular formula is C4H4N2O2, 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.

212 g of triphosgene (content 99%, 0.71 mol) was dissolved in 500 mL of nitrobenzene for use.In a device equipped with a reflux condenser, a thermometer, a stirrer and a constant pressure dropping funnel,Add 4,6-dihydroxypyrimidine (114 g, content 98%, 1 mol), triphenylphosphine oxide (8.4 g, content 99%,0.03 mol), cobalt phthalocyanine (0.57 g, 0.001 mol), stirred and mixed evenly,The temperature was raised to 90-95 C, and a solution of triphosgene in nitrobenzene was added dropwise.After 5 hours of reaction, the sample was analyzed, and the content of 4,6-dihydroxypyrimidine was 0.25% and the content of 4,6-dichloropyrimidine was 98.2% by HPLC. The reaction was completed.Vacuum distillation reaction mixture (oil bath temperature 95 C, vacuum -0.095 Mpa),143.8 g (content 99.7%) of 4,6-dichloropyrimidine was obtained in a yield of 96.2% (based on 4,6-dihydroxypyrimidine).

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. 1193-24-4, 4,6-Dihydroxypyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chongqing Ziguang Chemical Co., Ltd.; Ding Yongliang; Zhang Fei; Chen Xiaojian; Zhong Xianwei; Chen Yirou; (6 pag.)CN108341784; (2018); A;,
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. 32779-36-5, name is 5-Bromo-2-chloropyrimidine. A new synthetic method of this compound is introduced below., 32779-36-5

5-Bromo 2-chloro pyrimidine (2 g, 10.33 mmol, Combi-Blocks) was degassed for 30 mm. 1-Ethoxy vinyl tributyltin (4.1 mL, 11.3 mmol, Frontier Scientific) and bis(triphenylphosphine)palladium dichloride (0.36 g, 0.51 mmol) were added at rt. The resulting mixture was stirred overnight at 90 C. It was cooled to rt and filtered through celite. An aqueous HCI solution (6 N, 10 mL) was added and the mixture was stirred for1 hour at rt. It was neutralized with sat.NaHCO3 solution (15 mL), extracted with DCM (50 mL), dried over anhydrous Na2504 and concentrated. The crude product was purified by flash column chromatography to afford the title compound (pale yellow solid). 1H NMR (400 MHz, DMSO-d6): 6 8.90 (s, 2H), 2.65 (s, 3H). LCMS: (Method B) 162.0 (M+H), Rt. 4.6 mm, 98.01% (Max).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,32779-36-5, 5-Bromo-2-chloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; KULKARNI, Santosh, S.; GIRI, Awadut Gajendra; TORONTO, Dawn, V.; CROWE, David, Malcolm; (150 pag.)WO2017/144637; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia