Tag: M.W:200-300

Electric Literature of 1260682-15-2 ,Some common heterocyclic compound, 1260682-15-2, molecular formula is C5H3Cl3N2O, 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.

Intermediate AN(1)2,4-dichloro-6-(l-phenylvinyl)pyrimidin-5-yl)methanolA mixture of 2,4,6-trichloropyrimidin-5-yl)methanol (1.1 g), 1 -phenylvinylboronic acid (0.8 g), Tetrakis (0.3 g), sodium carbonate (1.64 g) in toluene (14 mL) and water (3 mL) was heated at 100 C for 12 h. Water was added followed by ethyl acetate, the aqueous layer was extracted with ethyl acetate (x3), and the combined organic layers were dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated, and the residue was purified Biotage eluting with 10-40% EtOAc/Hexanes to give the title compound as a white solid (325 mg). LC-MS (M+H)+ = 281.02. XH NMR (500 MHz, chloroform-i/) delta ppm 7.5 (5H, m), 6.01 (1H, s), 5.67 (1H, s), 4.62 (2H, s).

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. 1260682-15-2, (2,4,6-Trichloropyrimidin-5-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BOY, Kenneth M.; GUERNON, Jason M.; MACOR, John E.; OLSON, Richard E.; SHI, Jianliang; THOMPSON, Lorin A., III.; WU, Yong-Jin; XU, Li; ZHANG, Yunhui; ZUEV, Dmitry S.; WO2012/103297; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1060815-90-8, 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.1060815-90-8, name is 2-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H3ClIN3, molecular weight is 279.47, as common compound, the synthetic route is as follows.

Methyl 2-bromo-2-methylpropanoate (663 mL, 5.13 mmol) was added to 2-chloro-5- iodo-7H-pyrrolo[2,3-c/]pyrimidine (Preparation 74, 358.1 g, 1 .28 mol), potassium iodide (21 .3 g, 128 mmol) and cesium carbonate (1670 g, 5.13 mol) in DMF (7162 mL). The mixture was heated at 60C for 19 hours. The reaction mixture was diluted with water (7000 mL) and stirred at room temperature for 42 hours. The mixture was filtered and the solid was washed with water (500 mL) to afford the title compound as a beige solid in 92% yield, 445.8 g. 1H NMR (400 MHz, CDCl3): delta ppm 1.89 (s, 6H), 3.65 (s, 3H), 7.39 (s, 1 H), 8.56 (s, 1 H)

Statistics shows that 1060815-90-8 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; PFIZER LIMITED; ANDREWS, Mark, David; BAGAL, Sharanjeet, Kaur; BROWN, David, Graham; GIBSON, Karl, Richard; OMOTO, Kiyoyuki; RYCKMANS, Thomas; SABNIS, Yogesh; SKERRATT, Sarah, Elizabeth; STUPPLE, Paul, Anthony; WO2014/53967; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 53557-69-0, 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.53557-69-0, name is 6-Iodopyrimidin-4-amine, molecular formula is C4H4IN3, molecular weight is 221, as common compound, the synthetic route is as follows.

Step 9: 4-(6-Aminopyrimidin-4-yl)-1-(5-chloro-2-methylphenyl)-1 H-pyrrole-2-carbonitrilento a 50 mL round bottom flask equpped wfth a stir bar, condenser and 3-way vave connected to argon and vacuum 1 -(5-chloro-2-methylphenyl)-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-pyrrole-2-carbonitrile coming from the previous step, 6-iodopyrimidin-4-amine (663 mg, 3.0 mmol), 2M Na2003 (3.0 mL, 6.0 mmol) and dioxane (20 mL) were charged at room temperature. The resuWng reacton mixture was degassed three times back fAhng wfthfour times back flWng wfth argon each time and then warmed to 110 C for 1 h. The reacton mixture was coo?ed to room temperature, fUtered through a pad of Cehte, washed wfth EtOAc, and the fUtrate was concentrated and then dUuted wfth EtOAc and water. The two ayers were separated, and the aqueous ayer was extracted wfth EtOAc, The combned organic fractions were washed wfth aqueous brne, dried over Na2SO4, fNtered and concentrated under reduced pressure. The residue was purified by Biotage SP1 Elash Chromatography (DCM/MeOH/7N NH3 n MeOH95/5/05) to afford the tfte compound (291 mg, 47%, 2 steps).1H NMR (400 MHz, DMSO-d6) 8.33 (d, J = 0.98 Hz, 1 H), 7.96 (d, J = 1.7 Hz, 1 H), 7.64 – 7.69 (m, 2H), 7.55 – 7.61(m, 1H), 7.50-7.54 (m, 1H), 6.81 (s, 2H), 6.65 (d, J = 1.1 Hz, 1H), 2.10 (s, 3H).HRMS (ESI) m/z calcd for C16H12C1N5 + H 310.0854, found 310.0858.

Statistics shows that 53557-69-0 is playing an increasingly important role. we look forward to future research findings about 6-Iodopyrimidin-4-amine.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; BRASCA, Maria Gabriella; BINDI, Simona; CALDARELLI, Marina; NESI, Marcella; ORRENIUS, Sten Christian; PANZERI, Achille; WO2014/19908; (2014); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 43024-61-9 ,Some common heterocyclic compound, 43024-61-9, molecular formula is C9H9N3O3, 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.

Ethyl 7-hydroxypyrazolo[1,5-a]pyrimidine-6-carboxylate (Journal of Medicinal Chemistry, vol. 49, page 2526, 2006) (3.20 g, 15.5 mmol) was dissolved in phosphorus oxychloride (30 mL), N,N-diisopropylethylamine (5.4 mL, 30.9 mmol) was added, and the mixture was stirred with heating at 100 C. for 3 hr. After confirmation of consumption the starting materials, phosphorus oxychloride was evaporated under reduced pressure, and the residue was dissolved in ethyl acetate. The solution was added dropwise to a saturated aqueous sodium hydrogen carbonate solution under ice-cooling. To the saturated aqueous sodium hydrogen carbonate solution was added ethyl acetate, and the mixture was extracted 3 times. The combined organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.

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. 43024-61-9, Ethyl 7-hydroxypyrazolo[1,5-a]pyrimidine-6-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KYOWA HAKKO KIRIN CO., LTD.; Yamamoto, Keisuke; Aratake, Seiji; Hemmi, Kazuki; Mizutani, Mirai; Seno, Yuko; US2014/221340; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 60722-67-0, 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. 60722-67-0, name is 2-(Phenylmethoxy)-4-pyrimidinamine. A new synthetic method of this compound is introduced below.

KHMDS, 0.5M solution in toluene (5.95 mL, 2.98 mmol), was added to a stirred solution of the 2-(benzyloxy)pyrimidin-4-amine (0.50 g, 2.48 mmol) in toluene (15 mL) at 0C under nitrogen atmosphere. The reaction was stirred for 30 mm. In another flask, 4- iodobenzoic acid (1,85 g, 7.44 mmol) was dissolved in CH2CI2 (20 mL) under an N2. The solution was cooled to 0 C, oxalyichloride (0.65 mL, 5.16 mmol) was added dropwise followed by the addition of two drops of DMF. The reaction was allowed to stir for 30 mm, until the solution becomes clear. The mixture was concentrated under reduced pressure; the acid chloride formed was dissolved in dichloromethane (10 mL) added into the deprotonated aminopyrimidine dropwise. The reaction was allowed to warm to rt and was stirred overnight. The reaction was quenched with saturated solution of NH4CI (10 mL), extracted with EtOAc (3 x 10 mL). The combined fractions was washed with brine (10 mL) and dried with anhydrous Na2SO4, filtered and concentrated under reduced presure. Purification on silica gel using flash chromatography (10% EtOAc/hexanes) afforded the desired compound as a white solid. MP. 110 C. 1H NMR (500 MHz, CDCI3); ppm 8.50 (d, IH), 8.48 (br s, 1H), 7.96 (d, 1H), 7.88 (d, 2H), 7.60 (d, 2H), 7.47 (d, 2H), 7.38 (t, 2H), 7.34 (t, IH), 5.43 (s, 2H). ?3C NMR (100 MHz, CDCI3); ppm 165.4, 164.7, 160.9, 159.2, 138.5, 136.4, 132.8,128.9, 128.6, 128.2, 128.0, 104.4, 100.6, 69.3. IR(neat); 3303, 3061, 1695, 1585, 1516, 1402, 1288 cm-?. HRMS (ES) Calculated for C,8H,4N3O2Na1 m/z (M+Na) 454.0028, Obs?d.454.0030.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,60722-67-0, 2-(Phenylmethoxy)-4-pyrimidinamine, and friends who are interested can also refer to it.

Reference:
Patent; CURZA GLOBAL, LLC; THE UNIVERSITY OF UTAH RESEARCH FOUNDATION; REDDY, Hariprasada R. Kanna; SEBAHAR, Paul R.; SERRANO, Catherine M.; LOOPER, Ryan E.; (117 pag.)WO2019/13789; (2019); 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. 1211522-68-7, name is 4,6-Dichloro-3-methyl-1H-pyrazolo[3,4-d]pyrimidine, the common compound, a new synthetic route is introduced below. Application In Synthesis of 4,6-Dichloro-3-methyl-1H-pyrazolo[3,4-d]pyrimidine

To a solution of 2,4-dichloropyrrolo[1,2-f][1,2,4]triazine (4a) (0.5 g, 2.7 mmol) in 2-Propanol (6 mL) was added (S)-pyrrolidin-2-ylmethanol (0.39 mL, 4.0 mmol), DIPEA (1.39 mL, 8.0 mmol) and heated at 90 C for 1 hr. The reaction was cooled to room temperature and solid obtained was collected by filtration to afford (S)-(l-(2-chloropyrrolo[2,l-f][l,2,4]triazin-4- yl)pyrrolidin-2-yl)methanol (96a) (0.49 g, 73 % yield) as a white solid; NMR (300 MHz, DMSO-i/e): delta 7.70 (dd, J= 2.6, 1.4 Hz, 1H), 6.97 (dd, J= 4.7, 1.6 Hz, 1H), 6.80 – 6.57 (m, 1H), 5.15 (t, J = 5.7 Hz, 1H, D2O exchangeable), 4.87 (t, J= 5.7 Hz, 1H), 4.44 (d, J= 17.8 Hz, 1H), 4.05 – 3.82 (m, 1H), 3.72 – 3.39 (m, 2H), 2.22 – 1.84 (m, 4H). MS (ES+): 253.3, 255.3 (M+2); MS (ES-): 287.2, 289.2 (M+Cl).

The synthetic route of 1211522-68-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 60703-46-0, name is 2,4,6-Trichloro-5-methoxypyrimidine, molecular formula is C5H3Cl3N2O, 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 2,4,6-Trichloro-5-methoxypyrimidine

10. Preparation of 2,6-Dichloro-5-methoxy-pyrimidin-4-ylamine 2,4,6-Trichloro-5-methoxypyrimidine (1.0 g, 4.7 mmol, see U.S. Pat. No. 3,984,411 for preparation) was dissolved in 15 mL dry dimethyl sulfoxide (DMSO) and treated with a stream of ammonia gas for 30 min. The mixture was poured into 30 mL water and the precipitated product was collected by filtration and washed with water. This solid was dissolved in 40 mL ethyl acetate, washed twice with water, washed once with brine, dried and evaporated to give the title compound (800 mg, 88% yield): mp 155-156 C.: 1H-NMR (DMSO-d6+D2O) delta 3.71 (s, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 60703-46-0.

Reference:
Patent; Epp, Jeffrey B.; Schmitzer, Paul R.; Guenthenspberger, Katherine A.; Lo, William C.; Siddall, Thomas L.; US2009/62125; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 3438-55-9, 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 3438-55-9, name is 5-Bromo-4-chloro-6-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

5-Bromo-4-chloro-6-methylpyrimidine (65 mg, 0.31 mmcl), potassium trifluoro[4- (furo[3,2-c]pyridin-4-yloxy)-2-methylphenyl]borate (C44) (110 mg, 0.332 mmol), potassiumcarbonate (130 mg, 0.941 mmol), palladium(ll) acetate (0.40 mg, 0.0018 mmol) and dicyclohexyl(2,6-dimethoxybiphenyl-2-yl)phosphane (1 .20 mg, 0.0029 mmcl) were dissolved in nitrogen-purged ethanol, and the reaction mixture was heated to 85 00 for 66 hours. After cooling to room temperature, the reaction mixture was diluted with methanol and ethyl acetate, filtered through Celite, and concentrated under reduced pressure. Purification via silica gelchromatography (Gradient: 0% to 70% ethyl acetate in heptane) afforded the product as a colorless oil. Yield: 24 mg, 0.066 mmol, 21%. LCMS m/z 362.4 (M+H). 1H NMR (400 MHz, ODd3) oe 8.67 (s, 1H), 8.06 (d, J=5.9 Hz, 1H), 7.63 (d, J=2.0 Hz, 1H), 7.23 (d, J=5.9 Hz, 1H), 7.16-7.19 (m, 1H), 7.13 (dd, half of ABX pattern, J=8.2, 2.0 Hz, 1H), 7.09 (d, half of AB pattern, J=8.2 Hz, 1H), 6.80-6.84 (m, 1H), 4.32-4.52 (m, 2H), 2.25 (s, 3H), 2.06 (s, 3H), 1.28 (t, J=7.0Hz,3H).

According to the analysis of related databases, 3438-55-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; COE, Jotham, Wadsworth; ALLEN, John, Arthur; DAVOREN, Jennifer, Elizabeth; DOUNAY, Amy, Beth; EFREMOV, Ivan, Viktorovich; GRAY, David, Lawrence, Firman; GUILMETTE, Edward, Raymond; HARRIS, Anthony, Richard; HELAL, Christopher, John; HENDERSON, Jaclyn, Louise; MENTE, Scot, Richard; NASON, Deane, Milford, II; O’NEIL, Steven, Victor; SUBRAMANYAM, Chakrapani; XU, Wenjian; WO2014/72881; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 434941-55-6, 4-(4-Chlorophenyl)-2-(methylthio)pyrimidine, 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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

Step 2: At 0C, mCPBA (70% w/w; 483 mg, 2.02 mmol, 2.2 eq) is added portionwise to intermediate 19 (217 mg, 0.92 mmol, 1.0 eq) in DCM (5 mL). The reaction is stirred at r.t. for 2 h and the solid is filtered and washed with DCM. The organics is washed with saturated aqueous solution of NaHC03 and dried over anhydrous Na2S04. The solvent evaporated under reduced pressure to afford intermediate 20. LC-MS conditions: LC-MS 5

The synthetic route of 434941-55-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; AISSAOUI, Hamed; BOSS, Christoph; CIANA, Claire-Lise; SIEGRIST, Romain; WO2014/72903; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 313339-35-4, 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. 313339-35-4, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid. A new synthetic method of this compound is introduced below.

To a solution of 4,6-dichloro-2-methylsulfanylpyrimidine-5-carboxylic acid (5.5 mmol) indioxane (10 mL) are added diphenyl phosphoryl azide (6.6 mmol), triethylamine (6.6 mmol)and allyl alcohol (11 mmol) at room temperature under N2 atmosphere. After stirring at .100 C for 1 h, the reaction mixture is cooled to room temperature and diluted with AcOEt.The organic layer is washed twice with HaO and evaporated in vacua. The resulting residueis purified by silica gel column chromatography to give (4,6-dichloro-2-methylsulfanyl-pyrimidin-5-yl)carbamic acid allyl ester.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,313339-35-4, 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2006/18284; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia