Tag: M.W:200-300

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. 51940-64-8, name is Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate, molecular formula is C7H6Cl2N2O2, 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. Application In Synthesis of Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate

DIPEA (8.76 mL, 50.31 mmol) was added dropwise to a mixture of (ls,4s)-4-amino-1-methylcyclohexan-1-ol (5.00 g, 38.70 mmol) and ethyl2,4-dichloropyrimidine-5-carboxylate (8.55g, 38.70 mmol) in acetonitrile (143 mL) at -5C over a period of 15 min under air. The reaction5 mixture was stirred for 2 h, then was slowly allowed to warm tort, concentrated in vacuo, dilutedwith EtOAc (200 mL), and washed with water then with sat. brine. The organic layer was driedover MgS04, filtered and concentrated in vacuo. The resulting crude mixture was suspended inDCM (20 mL ), and the resulting solid was isolated by filtration and was washed with DCM ( 5 mL)to afford title compound (3.8 g). The filtrate was purified by fcc, elution gradient 0 to 70% EtOAc10 inn-heptane, to afford additional title compound (5.3 g). Both batches were combined to afford thetitle compound (9.10 g, 75%) as a white solid; 1H NMR (400 MHz, DMSO) 1.13 (3H, s), 1.32 (3H,t), 1.43 (2H, td), 1.53 – 1.61 (2H, m), 1.69 (4H, tt), 3.85- 3.99 (lH, m), 4.15 (lH, s), 4.32 (2H, q),8.27 (lH, d), 8.62 (lH, s); m/zMH+ 314.

With the rapid development of chemical substances, we look forward to future research findings about 51940-64-8.

Reference:
Patent; ASTRAZENECA AB; CANCER RESEARCH TECHNOLOGY LIMITED; FINLAY, Maurice, Raymond, Verschoyle; GOLDBERG, Frederick, Woolf; HOWARD, Martin, Richard; TING, Attilla, Kuan, Tsuei; (145 pag.)WO2019/238929; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 6214-47-7, Adding some certain compound to certain chemical reactions, such as: 6214-47-7, name is Ethyl 2-(4-chloropyrimidin-5-yl)acetate,molecular formula is C8H9ClN2O2, 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 6214-47-7.

To a nitrogen de-gassed solution of ethyl 2-(4-chloropyrimidin-5-yi)acetate {1108) (0.823 g, 4.10 mmol) in dry DMF (15 mL) were added triethylamine (1.715 mL, 12.31 mmoi) followed by triphenylphosphine (0.124 g, 0.473 mmol), trans- dichlorobis(triphenyl-phosphine)pailadium(ll) (0.144 g, 0.205 mmoi), Cu(l)l (0,078 g, 0.410 mmol) and finally (triethyisilyi)acetylene (1.470 mL, 8.204 mmol). The reaction mixture was then heated under microwave irradiation at 120 C for 25 minutes, concentrated in vacuo and purified by silica gel chromatography (isoiera Biofage, 40 g Si cartridge, 0-30% EtOAc in petroleum benzine 40-60 C) to give the title compound (1109) (1.176 g, 94% yield) as a yellow-orange oil; 1H NMR (400 MHz, CDCI3) delta 9.08 (s, 1 H), 8.68 (s, 1 H), 4.18 (q, J = 7.1 Hz, 2H), 3.80 (s, 2H), 1.26 (t, J = 7.1 Hz, 3H), 1.10 – 1.01 (m, 9H), 0.77 – 0.67 (m, 6H) LCMS Method C: rt 6.64 min; m/z 305.1 [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. 6214-47-7, Ethyl 2-(4-chloropyrimidin-5-yl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CANCER THERAPEUTICS CRC PTY LTD; DEVLIN, Mark Graeme; STREET, Ian Philip; TONG, Warwick Bonner; WO2014/27199; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1260169-02-5, 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 1260169-02-5, name is Ethyl 2-aminopyrazolo[1,5-a]pyrimidine-3-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

2-Aminopyrazolo [1,5-a] pyrimidine-3-carboxylic acidEthyl ester (1.60 g, 7.76 mmol),4-dimethylaminopyridine (0.19 g, 1.55 mmol)And triethylamine (3.25 mL, 23.28 mmol)Dissolved in dichloromethane (15 mL)And di-tert-butyl dicarbonate (3.30 mL, 15.52 mmol) was added thereto.After the resultant reaction solution was stirred at room temperature for 3 hours,Concentrate under reduced pressure.The resulting residue was purified by silica gel column chromatography (100% dichloromethane)The title compound was obtained as a yellow solid (1.24 g, 52.1%).

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 1260169-02-5, Ethyl 2-aminopyrazolo[1,5-a]pyrimidine-3-carboxylate.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; (88 pag.)CN104650092; (2017); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 659729-09-6, 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.659729-09-6, name is 4-Chloro-6-(4-(trifluoromethyl)phenyl)pyrimidine, molecular formula is C11H6ClF3N2, molecular weight is 258.63, as common compound, the synthetic route is as follows.

EXAMPLE 4 N-(5,6,7,8-Tetrahydronaphthalen-1-yl)-6-(4-(trifluoromethyl)phenyl)-pyrimidin-4-amine A mixture of 4-chloro-6-(4-(trifluoromethyl)phenyl) pyrimidine, Example 1(a), (0.26 g, 1.0 mmol) and 1,2,3,4-tetrahydro-1-naphthylamine (0.15 g, 1.0 mmol, Aldrich) in EtOH (1 mL) was heated in a microwave synthesizer at 120 C. for 15 min. The reaction mixture was evaporated under reduced pressure and the residue was dissolved in DCM. The DCM solution was washed with 10% sodium carbonate, dried over sodium sulfate and filtered. The filtrate was evaporated under reduced pressure and the residue purified by silica gel column chromatography (2:1:1 hexane/EtOAc/CHCl3) to give the title compound as an off-white amorphous solid. MS (ESI, pos. ion) m/z: 370.

The chemical industry reduces the impact on the environment during synthesis 659729-09-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Doherty, Elizabeth M.; Katon, Jodie; Norman, Mark H.; Retz, Daniel M.; Wang, Xianghong; Bo, Yunxin Y.; Tamayo, Nuria; Nishimura, Nobuko; Liao, Hongyu; US2006/241296; (2006); A1;,
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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. 444731-75-3, name is N-(2-Chloropyrimidin-4-yl)-N,2,3-trimethyl-2H-indazol-6-amine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 444731-75-3

A 250-mL 3-necked flask equipped with a magnetic stir bar, thermometer, reflux condenser, and nitrogen inlet/outlet was charged with ethanol (60 mL, 10 volumes), the product of Intermediate Example 4 (6.00 g, 20.85 mmol, 1.0 equiv) and 5-amino-2- methylbenzenesulfonamide (4.00 g, 21.48 mmol, 1.03 equiv) with stirring. The reaction mixture was heated to 70 0C. After stirring the reaction mixture at 68 – 72 0C for 3 hrs, 4M HCI in dioxane (0.11 mL, 0.44 mmol, 0.02 equiv) was charged over ca. 2 min. The reaction mixture was stirred at 68 – 72 0C until < 1.5% by area of the starting product of Intermediate Example 4 was remaining by HPLC analysis (Typically, this reaction is complete in > 8 hrs). The reaction mixture was cooled to 20 0C over ca. 30 min and stirred at 20 – 22 0C for 40 min. The product was then isolated by filtration and the filter cake washed with ethanol (20 mL, 3.3 volumes). The wet cake was dried under vacuum at 45 – 50 0C. The monohydrochloride salt of 5-({4-[(2,3-dimethyl-2/-/-indazol- 6-yl)(methyl)amino]-pyrimidin-2-yl}amino)-2-methylbenzenesulfonamide (9.52 g, 96.4%) was isolated as a white solid. 1H NMR (400 MHz, d6DMSO+NaHCO3) delta 9.50 (br s, 1 H), 8.55 (br s, 1 H), 7.81 (d, J = 6.2 Hz, 1 H), 7.75 (d, J = 8.7 Hz, 1 H), 7.69 (m, 1 H), 7.43 (s, 1 H), 7.23 (s, 2H), 7.15 (d, J = 8.4 Hz1 1 H), 6.86 (m, 1 H)1 5.74 (d, J = 6.1 Hz, 1 H), 4.04 (s, 3H), 3.48 (s, 3H), 2.61 (s, 3H)1 2.48 (s, 3H). MS (ES+, m/z) 438 (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, 444731-75-3, N-(2-Chloropyrimidin-4-yl)-N,2,3-trimethyl-2H-indazol-6-amine.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/20564; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 22276-95-5, name is 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 22276-95-5

N,O-Bis(trimethylsilyl)acetamide (BSA, 0.56 mL, 2.27 mmol) was added to a stirred suspension of 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (480 mg, 2.06 mmol) in dry acetonitrile (15 mL). After stirring at rt for 10 min, 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-d-ribofuranose (1.16 g, 2.31 mmol) was added, followed by the addition of trimethylsilyl trifluoromethanesulfonate (0.41 mL, 2.25 mmol). The reaction mixture was stirred at rt for 15 min, after which the flask was transferred to a preheated 80 C oil bath. After stirring for 1 h at 80 C, the reaction mixture was cooled to rt and diluted with EtOAc (75 mL). The organic phase was sequentially washed with aqueous saturated NaHCO3 solution and brine, dried (Na2SO4), filtered, and concentrated under reduced pressure to afford the crude nucleoside. Purification by flash column chromatography (silica gel, 20-100% EtOAc/hexanes gradient) provided (1) as a colorless foam (870 mg, 63%). TLC (silica gel, hexanes/ethyl acetate 3:1): Rf = 0.45. LRMS (ESI): 677.3, 675.2 and 673.2 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 22276-95-5.

Reference:
Article; Yu, Wenyu; Smil, David; Li, Fengling; Tempel, Wolfram; Fedorov, Oleg; Nguyen, Kong T.; Bolshan, Yuri; Al-Awar, Rima; Knapp, Stefan; Arrowsmith, Cheryl H.; Vedadi, Masoud; Brown, Peter J.; Schapira, Matthieu; Bioorganic and Medicinal Chemistry; vol. 21; 7; (2013); p. 1787 – 1794;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 36082-45-8, Adding some certain compound to certain chemical reactions, such as: 36082-45-8, name is 2-Amino-5-bromo-4-methoxypyrimidine,molecular formula is C5H6BrN3O, 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 36082-45-8.

Method 15; Synthesis of 4-methoxy-5-(4,4,5,5-tetramethyl- (1,3 ,2-dioxaborolan-2-yl))pyrimidine-2-ylamine; [0256] To a dry 200-mL flask was added 5-bromo-4-methoxypyrimidine-2- ylamine (2.88 g, 14.1 mmol), potassium acetate (4.16 g, 42.4 mmol), 4,4,5,5-tetramethyl- 2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l,3,2-dioxaborolane (3.76 g, 14.8 mmol) and dioxane (75 mL). Argon was bubbled through the solution for 15 minutes, at which time 1 , l’-bis(diphenylphosphino)ferrocene palladium(II) chloride dichloromethane adduct (0.58 g, 0.71 mmol). The reaction was refluxed in a 115 0C oil bath for 21 hours under argon. After cooling to room temperature, the dioxane was removed in vacuo. EtOAc (500 mL) was added and the resulting slurry was sonicated and filtered. Additional EtOAc (500 mL) was used to wash the solid. The combined organics were concentrated and the crude material was purified by silica gel chromatography (EtOAc as eluent) yielding 2.4 g of an off white solid. By 1H NMR the material was a 1 :1 mixture of boronate ester and 4-methoxypyrimidine-2-ylamine. The material was used as is in subsequent Suzuki reactions. LCMS (m/z): 170 (MH+ of boronic acid, deriving from in situ product hydrolysis on LC); 1H NMR (CDCl3): delta 8.42 (s, IH), 5.22 (bs, 2H), 3.90 (s, 3H), 1.34 (s, 12H).

According to the analysis of related databases, 36082-45-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS VACCINES AND DIAGNOSTICS, INC.; WO2008/98058; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 129872-81-7, 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 129872-81-7, name is 2,4-Dichloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: An oven-dried 15 mL pressure tube cooled under nitrogen, charged with 123 mg (0.61 mmol) of 2,6 dichloro-7-methyl-7H-purine (See US 20110086840 A1 for synthesis) and anhydrous ethanol/ DMF (0.5 mL/0.3 mL, 0.76M). N,N-diisopropylethylamine (0.130 mL,0.73mmol) was added via syringe followed by morpholine (0.064 mL, 0.73 mmol). The pressure tube was flushed with nitrogen and the septa replaced by a Teflon screw cap. The reaction mixture stirred overnight at room temperature. The reaction mixture was poured into 50 % ether/ethyl acetate and washed 1x with 50% brine and 1x with brine.The organic layer was dried (MgSO4), filtered , concentrated to yield 119 mg of crude product (77.6%) which was taken directly into the next step. 1H NMR (400MHz, DMSO d6) d 8.44 (s, 1H), 3.96 (s, 3H), 3.80 – 3.71(m, 4H), 3.53 – 3.44 (m, 4H). LC/MS-m/z FontWeight=”Bold” FontSize=”10″ 254.5 (M+H)+.

According to the analysis of related databases, 129872-81-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lee, Wendy; Ortwine, Daniel F.; Bergeron, Philippe; Lau, Kevin; Lin, Lichuan; Malek, Shiva; Nonomiya, Jim; Pei, Zhonghua; Robarge, Kirk D.; Schmidt, Stephen; Sideris, Steve; Lyssikatos, Joseph P.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 18; (2013); p. 5097 – 5104;,
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.36822-08-9, name is Benzo[4,5]thieno[3,2-d]pyrimidin-4(3H)-one, molecular formula is C10H6N2OS, molecular weight is 202.2324, as common compound, the synthetic route is as follows.Safety of Benzo[4,5]thieno[3,2-d]pyrimidin-4(3H)-one

Benzo[4,5]thieno[3,2-d]pyrimidin-4(3H)-one (10.78 g, 26.7 mmol) was treated with pyridine (2.68 mL, 33.3 mmol) and phosphoryl trichloride (53.4 mL, 573 mmol), then heated to reflux at 110 C. for 1 hr. Excess POC3was removed and cautiously quenched with ice water in an ice bath. The pH was adjusted to 5 with ammonium hydroxide. Solid was collected by filtration washed with water. The solid was dried to give 4-chlorobenzo[4,5]thieno[3,2-d]pyrimidine (10 g, 85% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,36822-08-9, Benzo[4,5]thieno[3,2-d]pyrimidin-4(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Universal Display Corporation; Joseph, Scott; Kwang, Raymond; Lee, Chi Hang; Shia, Chuan Jun; Ram, SiV Cheung; (131 pag.)KR2015/9461; (2015); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1044767-99-8, 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. 1044767-99-8, name is 5-Bromo-4-chloropyrimidin-2-amine. A new synthetic method of this compound is introduced below.

Step a: 5-bromo-4-chloropyrimidine-2-amine (2) (370.27 mg, 2.94 mmol), and 2-furancarbohydrazide (3a) (300 mg, 1.44 mmol), dissolved in 10 mL n-butanol At 120 C under nitrogen, the reaction was refluxed for 12 hours, concentrated under reduced pressure to remove the solvent, and subjected to silica gel column chromatography (CH2Cl2: MeOH = 10: 1) to obtain N ‘-(2-amino-5-bromopyrimidin-4-yl ) furan-2-carbohydrazide (4a)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1044767-99-8, 5-Bromo-4-chloropyrimidin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; Fudan University; Chang Jun; Wang Meiling; Jin Lin; Zhang Heyanhao; Niu Tong; (9 pag.)CN111018858; (2020); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia