Tag: M.W:200-300

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 941685-26-3, name is 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C12H18ClN3OSi

A 1000 mL round bottom flask was charged with 4-chloro-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (10.00 g, 35.23 mmol), 1-butanol (25.0 mL), 1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (15.66 g, 52.85 mmol), water (25.0 mL) and potassium carbonate (12.17 g, 88.08 mmol). This solution was degased 4 times, filling with nitrogen each time. To the solution was added tetrakis(triphenylphosphine)palladium(0) (4.071 g, 3.523 mmol). The solution was degased 4 times, filling with nitrogen each time. The mixture was stirred overnight at 100 C. After being cooled to room temperature, the mixture was filtered through a bed of celite and the celite was rinsed with ethyl acetate (42 mL). The filtrate was combined, and the organic layer was separated. The aqueous layer was extracted with ethyl acetate. The organic extracts were combined and concentrated under vacuum with a bath temperature of 30-70 C. to give the final compound 4-(1H-pyrazol-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine. Yield: 78%. LC-MS: 316.2 (M+H)+.

With the rapid development of chemical substances, we look forward to future research findings about 941685-26-3.

Reference:
Patent; Huang, Taisheng; Xue, Chu-Biao; Wang, Anlai; Kong, Ling Quan; Ye, Hai Fen; Yao, Wenqing; Rodgers, James D.; Shepard, Stacey; Wang, Haisheng; Shao, Lixin; Li, Hui-Yin; Li, Qun; US2011/224190; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 144927-57-1, Ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate, 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, Recommanded Product: Ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate, blongs to pyrimidines compound. Recommanded Product: Ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

To ethyl 4-chloro-7H-pyrrolo[2,3-if]pyrimidine-5-carboxylate (10.0 g, 44.3 mmol), (3-nitrophenyl)boronic acid (1 1.8 g, 70.9 mmol), PdCl2(dppf)-CH2Cl2 (3.62 g, 4.43 mmol) and aqueous sodium carbonate (2 M solution, 55.4 mL, 111 mmol) in a flask was added DMF (148 mL). The mixture was degassed for 10 minutes then heated at 1 15 C for 1.5 hours. The reaction was cooled to ambient temperature, then water was added and the mixture was extracted with DCM (*3) and EtOAc (*1). The combined organics were concentrated, diluted with EtOAc (300 mL) and washed with sorbitol/Na2C03 solution to remove excess boronic acid. The aqueous layer was extracted with EtOAc (x4). The combined organics were concentrated after which EtOAc and hexanes were added with stirring. The resulting precipitate was filtered to give solid product that was further triturated with DCM and hexanes to give ethyl 4-(3-nitrophenyl)-7H-pyrrolo[2,3- < ]pyrimidine-5-carboxylate. The combined organic fractions were concentrated under reduced pressure to give a residue containing product and DMF. Addition of MeOH and water led to formation of a precipitate which was filtered to afford additional ethyl 4-(3- nitrophenyl)-7H-pyrrolo[2,3-i ]pyrimidine-5-carboxylate. LRMS (ESI) calc'd for C,5Hi3N404 [M+H]+: 313, found 313. NMR (600 MHz, DMSO-D6) delta 13.17 (s, 1H), 8.99 (s, 1H), 8.43 (s, 1H), 8.39-8.36 (m, 2H), 8.12 (d, J= 7.8 Hz, 1H), 7.79 (t, J= 7.8 Hz, 1H), 3.93 (q, J= 7.2 Hz, 2H), 0.95 (t, J= 7.2 Hz, 3H). The synthetic route of 144927-57-1 has been constantly updated, and we look forward to future research findings. Reference:
Patent; MERCK SHARP & DOHME CORP.; AHEARN, Sean, P.; CHRISTOPHER, Matthew; JUNG, Joon; PU, Qinglin; RIVKIN, Alexey; SCOTT, Mark, E.; WITTER, David, J.; WOO, Hyun Chong; CASH, Brandon; DINSMORE, Christopher; GUERIN, David; WO2013/85802; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1152475-42-7, 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. 1152475-42-7, name is 7-Bromo-2-chlorothieno[3,2-d]pyrimidine, molecular formula is C6H2BrClN2S, 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.

7-Bromo-2-chlorothieno[3,2-d]pyrimidine (200 mg, 0.81 mmol) was dissolved in 2-butanol (4 mL) and then potassium carbonate (223 mg, 1.61 mmol) and 3,4,5-trimethoxybenzenamine (110 mg, 0.81 mmol) were added. After blowing nitrogen to the reaction mixture for 10 minutes, Pd2(dba)3 (50 mg, 0.048 mmol) and Xphos (35 mg, 0.073 mmol) were added. The reaction mixture was stirred at 80 C for 2.5 hours and then filtered with celite. The filtrate was diluted with ethyl acetate and washed with brine. The organic layer was dried with magnesium sulfate, filtered with celite, and then concentrated. Purification by chromatography (15% ethyl acetate/hexane) yielded the target compound (120 mg, 43% yield). [0504] 1H NMR (300 MHz, DMSO-d 6) delta 9.42 (s, 1H), 8.33 (s, 1H), 7.85 (s, 1H), 6.65 (s, 2H), 3.76 (s, 6H), 3.60 (s, 3H), MS m/z: 352.45 [M+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 1152475-42-7, 7-Bromo-2-chlorothieno[3,2-d]pyrimidine.

Reference:
Patent; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; SIM, Tae Bo; CHOI, Hwan Geun; HAH, Jung Mi; HAM, Young Jin; JUN, Eun Jin; LEE, Jung Hun; KIM, Hwan; WO2011/49332; (2011); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1013916-37-4, 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 1013916-37-4, name is 2-Chloro-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7(8H)-one. This compound has unique chemical properties. The synthetic route is as follows.

To a glass lined vessel was added 2-chloro-8-cyclopentyl-5-methyl-8/-/-pyrido[2,3-c]pyrimidin-7- one (9.35 g, 1.0 equiv.) along with acetonitrile (65 mL, 7.0 vol). N-Bromosuccinimide (9.67 g, 1.5 equiv.) and oxalic acid (0.65 g, 0.2 equiv.) were added. The reaction mixture was heated to 60¡À5 C. The reaction was stirred at 60C until starting material was consumed (at least 6 hours). The slurry was cooled to 20C and H20 (9 mL, 1 vol) was added. To the slurry was added a solution of sodium bisulfite (3.88 g, 1.0 equiv) in H20 (38 mL, 4 vol). The slurry was granulated for 1 hour, then filtered directly onto a 2 Whatman paper filter. The reaction vessel was washed with water (19 mL, 2 vol) followed by a 7:3 mix of methanol/acetonitrile (28 mL, 3 vol), and the washes were transferred onto the filter cake. The product was dried in the vacuum oven at 50-55C. 6-Bromo-2-chloro-8-cyclopentyl-5-methyl-8/-/-pyrido[2,3-c]pyrimidin-7-one (10.52 g; 87%) was isolated as a pale yellow solid.The product was further purified by recrystallization from toluene and n-heptanes. Toluene (60 mL, 6 vol) and 6-bromo-2-chloro-8-cyclopentyl-5-methyl-8/-/-pyrido[2,3-c]pyrimidin- 7-one (10.00 g, 1 equiv) were added to a reaction vessel and heated to 80C. The warm reaction mixture was filtered through an appropriate cartridge to ensure the removal of insoluble Pd and other insoluble contaminants. The filter cartridge was washed with 80C toluene (5 mL, 0.5 vol). The slurry was cooled to 25C at 1 C/min. n-Heptane (70 mL, 7 vol) was added to the reaction slurry at 1 mL/min. The slurry was further cooled to 0C at 1 C/min. The slurry was granulated at 0C for at least 1 hour.The slurry was filtered directly onto a 2 Whatman paper filter. n-Heptane (30 mL, 3 vol) was charged to the reaction vessel and the wash was transferred onto the filter cake and the product was dried in the vacuum oven at 50-55C. 6-Bromo-2-chloro-8-cyclopentyl-5-methyl-8/-/- pyrido[2,3-c]pyrimidin-7-one (8.73 g, 87%) was isolated as a cream colored solid.1H NMR (500 MHz, DMSO-de): delta 9.20 (s, 1 H), 5.82 (m, 1 H), 2.65 (s, 3H), 2.11 (m, 2H), 2.04 (m, 2H), 1.86 (m, 2H), 1.64 (m, 2H);13C NMR (125 MHz, DMSO-cfe): delta 158.2, 158.2, 157.6, 154.1 , 144.0, 120.9, 113.0, 54.4, 28.3, 25.7, 18.3; HRMS: Calcd for dsHuNsOi BnCli (M+H)+: 342.00033, Found: 342.00037.

According to the analysis of related databases, 1013916-37-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; CHEKAL, Brian Patrick; IDE, Nathan D.; WO2014/128588; (2014); 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.59549-51-8, name is 5-Bromo-2-chloro-4-(methylthio)pyrimidine, molecular formula is C5H4BrClN2S, molecular weight is 239.52, as common compound, the synthetic route is as follows.Quality Control of 5-Bromo-2-chloro-4-(methylthio)pyrimidine

A 3-L, 3-neck, round-bottom flask was equipped with a J-KEMtemperature controller, a mechanical stirrer, and a nitrogen inlet. The flask was charged with 5-bromo-2-chloro-4-(methylthio)pyrimidine (100 g, 417.5 mmol), (lr,4r)-4- aminocyclohexanol (76.4 g, 663.4 mmol), and ethanol (1 L). DIEA (109 mL,626.3 mmol) was added, and the mixture was heated to reflux overnight. TLC (1 : 1 hexanes/ethyl acetate) analysis after 20 h indicated complete reaction. The reaction was allowed to cool to room temperature. Water (300 mL) was added, and a precipitate gradually formed. The solid was filtered and washed with water to give 111.7 g of a white solid. The filtrate was extracted with ethyl acetate (3 x 300 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated to a semi-solid. The semi-solid was slurried in 1 : 1 hexanes/ethyl acetate and filtered to give an additional 12.1 g of a white solid. The two batches were combined to give 123.8 g (93%) of (lr,4r)- 4-(5-bromo-4-(methylthio)pyrimidin-2-ylamino)cyclohexanol as a white solid. MS (ESI) m/z 318, 320 [M+l]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,59549-51-8, 5-Bromo-2-chloro-4-(methylthio)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; BENNETT, Brydon, L.; ELSNER, Jan; ERDMAN, Paul; HILGRAF, Robert; LEBRUN, Laurie, Ann; MCCARRICK, Meg; MOGHADDAM, Mehran, F.; NAGY, Mark, A.; NORRIS, Stephen; PAISNER, David, A.; SLOSS, Marianne; ROMANOW, William, J.; SATOH, Yoshitaka; TIKHE, Jayashree; YOON, Won, Hyung; DELGADO, Mercedes; WO2012/145569; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 63558-65-6, 4-Chloro-5-iodopyrimidine, 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, Quality Control of 4-Chloro-5-iodopyrimidine, blongs to pyrimidines compound. Quality Control of 4-Chloro-5-iodopyrimidine

Under nitrogen, a mixture of 4-chloro-5-iodopyrimidine (2.0 g, 8.32 mmol), 2- (methylthio)-4-(tributylstannyl)pyrimidine (3.8 g, 9.15 mmol) and bis(triphenylphosphine)palladium(II) chloride (1.12 g, 1.60 mmol) in toluene (70 mL) was stirred for 16 h at 95 C. The reaction was quenched with a saturated solution of potassium fluoride. The mixture was extracted with ethyl acetate and washed with brine. The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by silica flash chromatography (ethyl acetate/petroleum ether 20:80) to afford the title compound (534 mg, 26.9% yield) as a yellow solid. LCMS (ESI): [M+H]+ = 239.1

At the same time, in my other blogs, there are other synthetic methods of this type of compound,63558-65-6, 4-Chloro-5-iodopyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; GENENTECH, INC.; BRAUN, Marie-Gabrielle; GIBBONS, Paul; LEE, Wendy; LY, Cuong Q.; RUDOLPH, Joachim; SCHWARZ, Jacob Bradley; ASHKENAZI, Avi; BEVERIDGE, Ramsay; ZHAO, Liang; LEMIRE, Alexandre; FU, Leo; LAI, Kwong Wah; WANG, Fei; (100 pag.)WO2020/56061; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 2915-16-4 ,Some common heterocyclic compound, 2915-16-4, molecular formula is C16H11ClN2, 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.

Preparation of Compound 13 [115] Compound 1-10 (2.7 g, 10.11 mmol), Compound 1-9 (5 g, 10.11 mmol), Pd(PPh3)4 (584 mg, 0.50 mmol), K2CO3(2M) (15 mL) and EtOH (15 mL) were dissolved in toluen (30 mL), and the mixture was heated at 120 . After the mixture was stirred for 3 hours, the reaction was completed. The reaction mixture was washed with distilled water and extracted with ethylacetate. After drying an organic layer with MgSO4 and removing a solvent by the rotary type evaporator, Compound 13 (5 g, 72%) was obtained through purification by column chromatography.

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. 2915-16-4, 2-Chloro-4,6-diphenylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.; KIM, Hye Mi; KIM, Young Gil; CHO, Young Jun; KWON, Hyuck Joo; KIM, Bong Ok; KIM, Sung Min; WO2011/93609; (2011); 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 35265-82-8, name is 2,4-Dichloro-6-methylthieno[3,2-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2,4-Dichloro-6-methylthieno[3,2-d]pyrimidine

[0151] To an acetic acid (15 mL) solution of 24-f (according to the synthesis procedure in the patent: WO 2007/023382A2) (992 mg, 4.6 mmol) and aluminum trichloride (1.23 g, 9.2 mmol) was slowly added a solution of bromine (0.72 mL,13.8 mmol) in acetic acid (5 mL) at room temperature. After dropwise addition, the reaction mixture was heated to 80Cand stirred for 6 hours. After cooling, the reaction mixture was poured into ethyl acetate (40 mL), washed with water (40mL), then 5% sodium thiosulfate solution (40 mL 3 2) to remove the color of bromine. The aqueous phase was extractedwith ethyl acetate (120 mL 3 2). The organic layers were combined and washed with saturated sodium bicarbonatesolution (100 mL) and saturated brine (200 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to givetitle compound 24-e (1.035 g, yield 76%) as a pale yellow solid. LC-MS (ESI): m/z 296.9 (M+H)+.

With the rapid development of chemical substances, we look forward to future research findings about 35265-82-8.

Reference:
Patent; Shanghai Yingli Science and Technology Co., Ltd; Shanghai Chemexplorer Co., Ltd.; XU, Zusheng; EP2860181; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 304693-64-9, 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. 304693-64-9, name is Ethyl 2-(trifluoromethyl)pyrimidine-5-carboxylate, molecular formula is C8H7F3N2O2, 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.

Intermediate B4-2-Trifluoromethyl-5-formylpyrimidine To a solution of ethyl 2-trifluoromethylpyrimidine-5-carboxylate (5.17 g) in toluene (120 ml) cooled in dry ice/acetone was added a solution of diisobutylaluminium hydride (25 wt %, 31 ml) over 15 min.The mixture was stirred at -78 C. for 45 min, then dilute HCl (2M, 120 ml) was added cautiously.After allowing the mixture to warm to room temperature diethyl ether was added.The organic phase was separated, washed with water, then brine, dried (MgSO4) and evaporated to give the title compound as a colourless solid (3.46 g, 84%).1H-NMR (CDCl3) delta 10.29 (1H, s), 9.37 (2H, s); 13C-NMR (CDCl3) delta 187.7, 159.6 (q, J=38 Hz), 159.1 (2C) 129.6, 119.2 (q, J=276 Hz).

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 304693-64-9, Ethyl 2-(trifluoromethyl)pyrimidine-5-carboxylate.

Reference:
Patent; SmithKline Beecham p.l.c.; US2004/167142; (2004); 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. 955368-90-8, name is 2-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one, the common compound, a new synthetic route is introduced below. Application In Synthesis of 2-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one

Compound 1.1 (255 mg, 1 mmol),2-allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (222 mg, 1 mmol),Cuprous iodide (191 mg, 1 mmol),Anhydrous potassium carbonate (276 mg, 2 mmol)And N,N-dimethylethylenediamine (88 mg, 1 mmol)Add to 1,4-dioxane (20 mL),The reaction system was stirred at 100 C overnight.The reaction solution was then cooled to room temperature.filter,The filtrate is concentrated,The residue was purified by silica gel column chromatography (EtOAc /EtOAcCompound 1-1 (205 mg, yield: 52%) was a red liquid.

The synthetic route of 955368-90-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Dinuo Pharmaceutical Technology Co., Ltd.; Zhao Zhiming; Gao Daxin; Chen Shoujun; Wu Zhiheng; (105 pag.)CN108623615; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia