Category: pyrimidines

Application of 2927-71-1, 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.2927-71-1, name is 2,4-Dichloro-5-fluoropyrimidine, molecular formula is C4HCl2FN2, molecular weight is 166.9685, as common compound, the synthetic route is as follows.

A solution of HOAc (2.4 g, 0.04 mol) in THF (15 mL) was added drop wise to a refluxing mixture of dichloro-5-fluoro-pyrimidine (3.34 g, 0.02 mol) and Zn (7.8 g, 0.02 mol) in THF (40 mL) over a 1-hour period. The mixture was refluxed for another 9 h. After cooling to room temperature, the solution was filtered to remove an insoluble solid. The solution containing 2-chloro-5-fluoro-pyrimidine was used directly in the next step reaction.

Statistics shows that 2927-71-1 is playing an increasingly important role. we look forward to future research findings about 2,4-Dichloro-5-fluoropyrimidine.

Reference:
Patent; Kalypsys, Inc.; US2005/234046; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 939979-43-8, name is 5,7-Dichloro-3-methylpyrazolo[1,5-a]pyrimidine, the common compound, a new synthetic route is introduced below. COA of Formula: C7H5Cl2N3

5,7-Dichloro-3-methyl-pyrazolo[l,5-a]pyrimidine (190 mg, 938.52 mupiiotaomicron, 1 eq), (5-fluoro-3- pyridyl)boronic acid (138.86 mg, 985.45 muiotaetaomicron, 1.05 eq), Pd(dppf)Cl2 (68.67 mg, 93.85 muiotaetaomicron, 0.1 eq) and Cs2C03 (611.58 mg, 1.88 mmol, 2 eq) were taken up into a microwave tube in 1,4-dioxane (3 mL) and H20 (1 mL). The sealed tube was heated at 110 C for 1 h under microwave. The mixture was concentrated and water (10 mL) was added. The mixture was extracted with EtOAc (20 mL x 3). The combined organic layers were dried over Na2S04, filtered and concentrated to yield a residue which was purified on silica gel column chromatography (from PE/EtOAc = 1/0 to 10/3, TLC: PE/EtOAc = 3/1, Rf = 0.50) to yield 5-chloro-7-(5-fluoro-3-pyridyl)-3-methyl- pyrazolo[l,5-a]pyrimidine (130 mg, 494.92 mupiiotaomicron, 52.7% yield, 100.0%) purity) as a yellow solid. NMR (400 MHz, CDC13) delta ppm 8.97 (s, 1H), 8.69 (d, J = 2.7 Hz, 1H), 8.38-8.31 (m, 1H), 8.04 (s, 1H), 6.92 (s, 1H), 2.40 (s, 3H); ES-LCMS m/z 263.0, 265.0 [M+H]+.

The synthetic route of 939979-43-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KYN THERAPEUTICS; CASTRO, Alfredo C.; EVANS, Catherine Anne; (632 pag.)WO2018/195397; (2018); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 50270-27-4 ,Some common heterocyclic compound, 50270-27-4, molecular formula is C5HCl3N2O, 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 2,4,6-trichloropyrimidine-5-carbaldehyde (2 g, 9.46 mmol) in EtOH (25 mL) at -78 °C under argon were added tert-butylhydrazine hydrochloride (1.18 g, 9.46 mmol) and TEA (6 mL, 42.57 mmol) dropwise. The mixture was stirred at -78 °C for 2 h, then at 0 °C for 3 h. The mixture was then concentrated under reduced pressure onto Celite and purified by silica gel chromatography eluting with 0- 1percent) MeOH in DCM to afford l-tert-butyl-4,6-dichloro-lH-pyrazolo[3,4-d]pyrimidine (1.7 g, 73percent) as an oil that solidified upon standing. LCMS (ESI) m/z 245 (M + H)+.

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. 50270-27-4, 2,4,6-Trichloropyrimidine-5-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; CHAO, Qi; HADD, Michael, J.; HOLLADAY, Mark, W.; ROWBOTTOM, Martin; WO2012/30924; (2012); A1;,
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. 3177-24-0, name is 2,4-Dichloropyrimidine-5-carbonitrile. A new synthetic method of this compound is introduced below., COA of Formula: C5HCl2N3

Intermediate 14: Ethyl 3-[3-({[4-chloro-5-cyanopyrimidin-2-yllamino}methyl)-2- methylphenyllbenzoate:2,4-Dichloro-pyrimidine-5-carbonitrile (50 mg, 0.287 mmol, 1 .0 eq) was dissolved in DMF (1 ml) and intermediate 7 (77 mg, 0.287 mmol, 1.0 eq) was added to the solution, followed by DIEA (51 ul, 0.287 mmol, 1 .0 eq). The reaction mixture was stirred for 1 hour at room temperature, diluted with EtOAc (50 ml) and washed with water (50 ml x4). The organic fraction was dried over anhydrous Na2S04, filtrated and concentrated under reduced pressure and purified by preparative HPLC to yield the desired intermediate 14.

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, 3177-24-0, 2,4-Dichloropyrimidine-5-carbonitrile.

Reference:
Patent; AMAKEM NV; LEYSEN, Dirk; DEFERT, Olivier; BOLAND, Sandro; WO2012/156467; (2012); 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. 5993-98-6, name is 4-Chloro-2-methyl-6-(trifluoromethyl)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 4-Chloro-2-methyl-6-(trifluoromethyl)pyrimidine

To benzyl (7S)-7-methyl-5-(2-(1,3-thiazol-2-yl)benzoyl)-1,2,5-oxadiazepane-2-carboxylate (88 mg) obtained in Step A of Example 84 was added 5.1M hydrogen bromide acetic acid solution (2.0 mL), and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated under reduced pressure, and a mixture of the residue, ethanol (2.0 mL), acetic acid (0.012 mL) and 4-chloro-2-methyl-6-trifluoromethylpyrimidine (43.5 mg) was stirred in a microwave reactor at 150 C. for 0.5 hr. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate), and crystallized (hexane/diisopropyl ether) to give the title compound (45 mg). MS: [M+H]+ 464.0.

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, 5993-98-6, 4-Chloro-2-methyl-6-(trifluoromethyl)pyrimidine.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KAMEI, Taku; ARIKAWA, Yasuyoshi; OHASHI, Tomohiro; IMAEDA, Toshihiro; FUJIMORI, Ikuo; MIKI, Takashi; YONEMORI, Jinichi; OGURO, Yuya; SUGIMOTO, Takahiro; SETO, Masaki; NISHIDA, Goushi; KAMATA, Makoto; IMOTO, Hiroshi; (132 pag.)US2018/155333; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1224288-92-9, 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. 1224288-92-9, name is 5-Chloropyrazolo[1,5-a]pyrimidine-3-carbonitrile. A new synthetic method of this compound is introduced below.

To a mixture of 5-chloropyrazolo[1,5-ajpyrimidine-3-carbonitrile (40.00 mg, 223.99 umol, 1.00 eq) and 3- [(2R)-4,4-difluoropyrrolidin-2-ylj -5-fluoro-pyridine (61.62 mg, 223.99 umol, 1.00eq) in n-BuOH (2.00 mL) was added DIPEA (144.74 mg, 1.12 mmol, 5.00 eq). The resulting mixture was stirred at 100C for 16 hrs. The mixture was concentrated and the crude product was purified by acidic prep-HPLC (TFA system). (R)-5-(4,4-difluoro-2-(5-fluoropyridin-3 – yl)pyrrolidin- 1 -yl)pyrazolo [1 ,5-ajpyrimidine-3 -carbonitrile (48.70 mg, 85.09 umol, yield: 38%) was obtained as a brown solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1224288-92-9, its application will become more common.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; WENGLOWSKY, Steven, Mark; MIDUTURU, Chandrasekhar, V.; BIFULCO, Neil, Jr; KIM, Joseph, L.; (91 pag.)WO2017/87778; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 2434-53-9, 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. 2434-53-9, name is 6-Amino-1-methylpyrimidine-2,4(1H,3H)-dione, molecular formula is C5H7N3O2, 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.

6-Amino-1-methylpyrimidine-2,4-dione (10.0 g, 70.1 mmol) was dissolved in water (100 mL). Hydrochloric acid (7 mL, 84.0 mmol, 12 N) was added dropwise at 0C while stirring. Then sodium nitrite (5.80 g, 84.2 mmol) was dissolved in water (50 mL) and added dropwise to the reaction solution to give a purple precipitate. The reaction was stirred at 25C for 2 hours, filtered and washed with cold water to give a purple solid. The solid was dissolved in water (100 mL) and sodium hydrosulphite (18.7 g, 118 mmol) was added in batches while stirring, heated to 60C and stirred for 0.5 h, cooled to 25C and stirred for 16 h, filtered, washed with cold water (50 mL), ethanol (50 mL), acetone (50 mL) respectively, and dried to give 5,6-diamino-1-methylpyrimidine-2,4-dione (8.60 g, as a pale yellow solid) with a yield of 93%. 1H NMR (400 MHz, DMSO-d6) delta 10.49(br, 1H), 6.15(br, 2H), 3.25(s, 3H), 2.95(br, 2H). MS-ESI calcd. [M + H]+ 157, found 157.

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 2434-53-9, 6-Amino-1-methylpyrimidine-2,4(1H,3H)-dione.

Reference:
Patent; GUANGDONG ZHONGSHENG PHARMACEUTICAL CO., LTD; WU, Lingyun; CHEN, Xiaoxin; ZHANG, Peng; LIU, Xing; ZHANG, Li; LIU, Zhuowei; CHEN, Shuhui; LONG, Chaofeng; (160 pag.)EP3299371; (2018); A1;,
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. 137281-39-1, name is 4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid. A new synthetic method of this compound is introduced below., Recommanded Product: 4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid

General procedure: To a suspension of compound 6 (0.033 mmol) in N,N-dimethylformamide (5 mL), corresponding amine (RNH2) (0.033 mmol) and DIPEA (0.1 mmol) were added at about 10 C under nitrogen atmosphere. To this, diethylphosphorocyanidate(0.04 mmol) was added slowly over a period of 15 min. The resultant solution was stirred for 3 h at about 10 C. The reaction was complete by TLC (TLC system: 10% methanol in chloroform). Reaction was slowly quenched using saturated sodium-bi-carbonate solution and the resulted solid was stirred for 30min. Solid was collected by filtration and the wet cake was washed with saturated sodium-bi-carbonate solution. Upon drying the wet cake for an hour under vacuum, it was further suspended in methanol and stirred for 30 min, filtered, collected and dried to get respective pure compounds.

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, 137281-39-1, 4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid.

Reference:
Article; Balaraman, Selvakumar; Nayak, Nagaraj; Subbiah, Madhuri; Elango, Kuppanagounder P.; Medicinal Chemistry Research; vol. 27; 11-12; (2018); p. 2538 – 2546;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 111196-81-7, 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.111196-81-7, name is 2-Chloro-5-ethylpyrimidine, molecular formula is C6H7ClN2, molecular weight is 142.59, as common compound, the synthetic route is as follows.

General procedure: To a vial with septa containing tert-butyl 2-[(R)-5-bromo-2,3-dihydro-1H-inden-1-yl]-2,7-diazaspiro[3.5]nonane-7-carboxylate 3 (2.42 mmol) were added bis(pinacolato)diboron (2.61 mmol), potassium acetate (12.12 mmol), and Pd(dppf)Cl2 (0.039 mmol). The vial was purged with a stream of nitrogen, and anhydrous 1,4-dioxane (12 mL) was added. The resulting mixture was purged with nitrogen for three times, and the mixture was heated at 95 C for 1 h. The aryl halide 5 (2.61 mmol), Pd(dppf)Cl2 (0.062 mmol), and 9 ml of 2 M aqueous potassium carbonate solution (de-oxygenated by bubbling through N2 for 15 min) were added. The mixture was purged with N2 three times and heated at 95 C for 17 h. The mixture was cooled to room temperature and the organic layer was separated from the aqueous layer. The organic layer was filtered through a thin plug of silica gel, and rinsed with 5 mL of isopropyl alcohol followed by 5 mL of MeOH. The filtrate and the washings were concentrated under reduced pressure to give the crude product that was purified by silica gel chromatography eluting with a gradient of 010% MeOH in CH2Cl2 to give the desired product.

Statistics shows that 111196-81-7 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-ethylpyrimidine.

Reference:
Article; Fernando, Dilinie P.; Jiao, Wenhua; Polivkova, Jana; Xiao, Jun; Coffey, Steven B.; Rose, Colin; Londregan, Allyn; Saenz, James; Beveridge, Ramsay; Zhang, Yingxin; Storer, Gregory E.; Vrieze, Derek; Erasga, Noe; Jones, Ryan; Khot, Vishal; Cameron, Kimberly O.; McClure, Kim F.; Bhattacharya, Samit K.; Orr, Suvi T. M.; Tetrahedron Letters; vol. 53; 47; (2012); p. 6351 – 6354,4;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 46155-89-9, 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 46155-89-9, name is 1,3-Dimethyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione. This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 3 1 ,3,7-Trimethyl- lH-pyrrolo[3,2-^]pyrimidine-2,4(3H,5H)-dioneCH3CH3Step 1 l,3-Dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-l//-pyrrolo[3,2-c/]pyrimidine-7- carbaldehyde: At a temperature of 5-10C, phosphorous oxychloride (1.84 ml, 20.087 mmol) was mixed with iV.iV-dimethylformamide (2 mL). Then a solution of Intermediate 1 (600 mg, 3.348 mmol) in vV.jV-dimethylformamide (3 mL) was added while stirring. The reaction mixture was held for 2 h at 950C, cooled and poured onto ice (10 g). The precipitate formed was filtered off and recrystallised from water to give 300 mg of the product as an off-white solid; 1H NMR (delta ppm, 300 MHz, DMSO-^6) 3.25 (s, 3H), 3.75 (s, 3H), 8.06 (s, IH), 9.79 (s, IH), 13.15 (br s, IH); APCI-MS (m/z) 208.20 (M+H)+.

According to the analysis of related databases, 46155-89-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; CHAUDHARI, Sachin, Sundarlal; KUMAR, Sukeerthi; THOMAS, Abraham; PATIL, Nisha, Parag; KADAM, Ashok, Bhausaheb; DESHMUKH, Vishal, Govindrao; DHONE, Sachin Vasantrao; CHIKHALE, Rajendra, Prakash; KHAIRATKAR-JOSHI, Neelima; MUKHOPADHYAY, Indranil; WO2010/109287; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia