Tag: M.W:100-200

Synthetic Route of 13316-12-6, Adding some certain compound to certain chemical reactions, such as: 13316-12-6, name is 7-Chlorothiazolo[5,4-d]pyrimidine,molecular formula is C5H2ClN3S, 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 13316-12-6.

A solution of 4-[3-(1-aminoethyl)-5-chloro-2-ethoxy-6-fluorophenyl]pyrrolidin-2-one (30 mg, 0.333 mmol) and 7-chloro[1,3]thiazolo[5,4-d]pyrimidine (25.7 mg, 0.15 mmol) [AK-58025, Ark Pharm] in 1-butanol (6.6 mL) was treated with N,N-diisopropylethylamine (0.052 mL, 0.30 mmol) and heated at 114 C. for 2.5 h. The reaction mixture was then concentrated to a yellow residue. Purification by preparative LCMS (pH 2) afforded the title product (0.033 g, 60%) as a white solid as a mixture of four diastereoisomers. 1H NMR (300 MHz, DMSO-d6) delta 9.30 (s, 1H), 8.78 (d, J=8.4 Hz, 1H), 8.37 (d, J=1.8 Hz, 1H), 7.82 (s, 1H), 7.71 (d, J=8.3 Hz, 1H), 5.91-5.70 (m, 1H), 4.29-4.14 (m, 1H), 4.13-3.96 (m, 1H), 3.95-3.81 (m, 1H), 3.60 (dd, J=9.3, 9.3 Hz, 1H), 3.26 (dd, J=7.8, 7.3 Hz, 1H), 2.42-2.21 (m, 2H), 1.59-1.32 (m, 6H); LCMS calculated for C19H20ClFN5O2S (M+H)+: m/z=436.1. found: 435.9.

According to the analysis of related databases, 13316-12-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INCYTE CORPORATION; Li, Yun-Long; Combs, Andrew P.; US2015/361094; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1193-24-4 , The common heterocyclic compound, 1193-24-4, name is 4,6-Dihydroxypyrimidine, molecular formula is C4H4N2O2, 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.

EXAMPLE 21:; 6-(3-f4-(2-terf-Butvl-6-cvclobutvl-pvrimidin-4-vl)-piperazin-1-vn-propoxv)-pyrimidin-4-ol; 1.5 g of 2-tert-Butyl-4-[4-(3-chloro-propyl)-piperazin-1-yl]-6-cyclobutyl-pyrimidine (4.27 mmol), 0.72 g of pyrimidine-4,6-diol (6.4 mmol) and 1.31 g of triethylamine in 30 ml of dimethylformamide were stirred for 16 h at 80C. The mixture was extracted with water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated to dryness. The crude product was purified by chromatography on silica gel using dichloromethane-methanol (1-10%). Fractions containing the product were combined. The solvents were evaporated and the oily residue was treated with acetonitrile. The precipitate was collected by filtration and dried to yield 0.27 g of the title compound.MS (ESI) m/z: 427.2 [M+H]+1H-NMR (DMSO): 5 [ppm] 8.1 (s, 1H), 6.4 (s, 1H), 5.5 (s, 1H), 4.15 (m, 2H), 3.6 (m, 4H), 3.4 (m, 2H), 2.4 (m, 6H), 2.25 (m, 2H), 2.15 (m, 2H), 1.95 (m, 1H), 1.85 (m, 2H), 1.8 (m, 1H), 1.3 (s, 9H).

The synthetic route of 1193-24-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT GMBH & CO. KG; WO2006/15842; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 7752-82-1, 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. 7752-82-1, name is 5-Bromopyrimidin-2-amine. A new synthetic method of this compound is introduced below.

2-Amino-5-bromopyrimidine (210 mg, 1.21 mmol) was suspended in toluene (10 mL), the suspension was added with sodium t-butoxide (200 mg, 2.08 mmol), morpholine (2.99 g, 34.3 mmol), tris(dibenzylideneacetone)dipalladium(0) (31.2 mg, 0.03 mmol) and (2-biphenyl)di-t-butylphosphine (36.0 mg, 0.12 mmol), and the mixture was stirred at 110 C. for 66 hours in an argon atmosphere. The reaction mixture was directly separated by silica gel column chromatography, and then purified by preparative silica gel thin layer chromatography to obtain 2-amino-5-(4-morpholino)pyrimidine as pale yellow solid (43.6 mg, 20%).1H-NMR (CDCl3) delta: 3.02 (4H, t, J=4.6 Hz), 3.86 (4H, t, J=4.6 Hz), 4.80 (2H, br), 8.06 (2H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7752-82-1, 5-Bromopyrimidin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; Kowa Company, Ltd.; US2009/54474; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 32779-36-5 ,Some common heterocyclic compound, 32779-36-5, molecular formula is C4H2BrClN2, 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.

In a microwave vial were mixed: 1,1-dimethylethyl 1-piperazinecarboxylate (110 mg, 0.589 mmol, available from Fluke), 5-bromo-2-chloropyrimidine (95 mg, 0.491 mmol, available from Lancaster) and DIPEA (0.112 mL, 0.638 mmol) in tert-butanol (2 mL). The reaction was stirred and heated in an Emrys Optimizer microwave at 150 C. for 0.5 hr. The reaction mixture was partitioned between EtOAc (20 mL) and water (20 mL) and the organic layer washed with brine (20 mL) before being dried through an hydrophobic frit and concentrated to yield the desired product (162.3 mg)LCMS (Method C): Rt=1.26, MH+=343

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; Demont, Emmanuel Hubert; Garton, Neil Stuart; Gosmini, Romain Luc Marie; Hayhow, Thomas George Christopher; Seal, Jonathan; Wilson, David Matthew; Woodrow, Michael David; US2012/208798; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 10320-42-0, Adding some certain compound to certain chemical reactions, such as: 10320-42-0, name is 2-Chloro-5-nitropyrimidine,molecular formula is C4H2ClN3O2, 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 10320-42-0.

To a solution of 36 (400 mg, 2.5 mmol) in HOAc (5 mL) is added Fe (700 mg.12.5 mmoi). After stirring at 75 C for 2 hours, the mixture is cooled to room temperature, filtered, concentrated, and purified by silica gel column chromatography (F:A:PE == 1:5) to give 37 as as an oil (320 mg. 98% yield). (MS: [M+Hj 1300)

According to the analysis of related databases, 10320-42-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IMMUNE SENSOR, LLC; THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; ZHONG, Boyu; SUN, Lijun; SHI, Heping; LI, Jing; CHEN, Chuo; CHEN, Zhijian; (270 pag.)WO2017/176812; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 933702-55-7, 2-Chloropyrimidine-5-carbaldehyde, 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, 933702-55-7, blongs to pyrimidines compound. Application In Synthesis of 2-Chloropyrimidine-5-carbaldehyde

To a solution of 2-chloropyrirnidine-5-carbaldehyde (0.30 g, 2.11 mmol) in THE (10 mL) was added intermediate 74 (0.36 g, 1.75 mmoi) and the reaction mixture was stirred at ambient temperature for 1 h. To the resulting solution was added sodium cyanoborohydride (0.27 g, 4.38 mmoi) and MeOH (mu.) and stirring was continued for 14 h. The reaction mixture was dilutedwith water (20 mL) and extracted with 7% MeOH:DCM (3 x 30 mL), The combined organic layers were dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was triturated with DCM/n-hexane to obtain Intermediate 98 (0.45 g, 43.00%), ?Fl NMR (400 MHz, DMSO-d6) ppm 2.23 (s, 3 H), 2.59-2.67 (rn, 2 H), 3.17 (d, J 4.16 Hz, I H), 3.80 (s, I H), 4.57 (d, J= 4.65 Hz, I H), 5.01 (d, J= 3.67 Hz, I H), 5.38 (d, J= 3.42 Hz, 2El), 5.48 – 5.62 (m, I H). 7.56 – 7.74 (m, 2 H). 8.64 – 8.76 (m, 2 H). LCMS (Aithod-O): retention time 0.72 mm, [M+H1 334.5

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,933702-55-7, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GUNAGA, Prashantha; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; PANDA, Manoranjan; YADAV, Navnath Dnyanoba; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (321 pag.)WO2018/93569; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 13036-57-2, 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. 13036-57-2, name is 2-Chloro-4-methylpyrimidine. A new synthetic method of this compound is introduced below.

Step B: 2-Propen-1-yl {3-[(2-chloro-4-pyrimidinyl)acetyl]phenyl}carbamate; Ethyl 3-{[(2-propen-1-yloxy)carbonyl]amino}benzoate (20.0 g, 80.24 mmol) was dissolved in 1 M LiHMDS in THF (260 mL) and cooled to 0 C. A solution containing 2-chloro-4-methylpyrimidine (10.32 g, 80.24 mmol) in 20 mL dry THF was added to the reaction mixture. The reaction was stirred at 0 C. for 2 h, quenched with MeOH (100 mL), dried directly onto silica, and purified via flash chromatography EtOAc/CH2Cl2 0-100% gradient run over 60 min. The desired fractions were combined and the solvent was removed to give the title compound (13.6 g, 51% yield); ES-LCMS m/z 332 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13036-57-2, 2-Chloro-4-methylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Adams, Jerry Leroy; Dickerson, Scott Howard; Johnson, Neil W.; Kuntz, Kevin; Petrov, Kimberly; Ralph, Jeffrey M.; Rheault, Tara Renae; Schaaf, Gregory; Stellwagen, John; Tian, Xinrong; Uehling, David Edward; Waterson, Alex Gregory; Wilson, Brian; US2009/298815; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 582313-57-3, 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 582313-57-3 as follows.

This compound is synthesized using a procedure such as that described by ?.Vorbruggen and U. Niedballa in J. Org. Chem., 39: 3654-3660 (1974). The 4-chloro-5-fluoro-7H- pyrrolo[2,3-d]pyrimidine (1?) used in this transformation is prepared following the procedure described by A. B. Eldrup, et al. in J. Med. Chem.. 47: 5284 (2004).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,582313-57-3, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2006/65335; (2006); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 29274-24-6 ,Some common heterocyclic compound, 29274-24-6, molecular formula is C6H4ClN3, 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.

N-Iodosuccinimide (1.61 g, 7.16 mmol) was added to a solutionof 5-chloropyrazolo[1,5-a]pyrimidine (7) (1 g, 6.51 mmol) in anhydrousDMF (10 mL). After stirring at RT for 4 h the reaction was poured into 10% sodium thiosulfate (75 mL). The resulting precipitate was isolated via filtration and dried (Whatman PS1 filterpaper) to give 19 as a pale brown solid (1.62 g, 89%). 1H NMR deltaH (d6-DMSO, 300 MHz), 9.19 (d, J 7.2, 1H), 8.38 (s, 1H), 7.18 (d, J7.2, 1H). LC-MS tR 6.37 min; LC254 99%; m/z 280.1/282.0 [M+H].This was used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,29274-24-6, its application will become more common.

Reference:
Article; Phillipson, Louisa J.; Segal, David H.; Nero, Tracy L.; Parker, Michael W.; Wan, Soo San; De Silva, Melanie; Guthridge, Mark A.; Wei, Andrew H.; Burns, Christopher J.; Bioorganic and Medicinal Chemistry; vol. 23; 19; (2015); p. 6280 – 6296;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 62802-42-0, 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 62802-42-0, name is 2-Chloro-5-fluoropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Step 1: (0552) To 2-chloro-5-fluoropyrimidine (2 g, 15 mmol) in a 250-mL round bottom flask was added DMA (8 mL), tris(dibenzylideneacetone)dipalladium (0.544 g, 0.6 mmol), 1,1?-bis(diphenylphosphino)ferrocene (0.67 g, 1.2 mmol), zinc cyanide (1.15 g, 9.8 mmol), and zinc dust (0.237 g, 3.62 mmol). The flask was capped, flushed with nitrogen, and stirred for 2.5 h at 100 C. The reaction was cooled to room temperature, filtered through celite, and washed with DCM. The filtrate was poured into water and extracted with DCM. The combined organic layers were dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-10% EtOAc/hexanes over 20 minutes) to provide the nitrile compound (0.58 g, 31%).

According to the analysis of related databases, 62802-42-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; Scott, Jack D.; Stamford, Andrew W.; Gilbert, Eric J.; Cumming, Jared N.; Iserloh, Ulrich; Misiaszek, Jeffrey A.; Li, Guoqing; US2015/307465; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia