Month: August 2021

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. 51421-99-9, name is 4-Chloro-2-methoxypyrimidine, molecular formula is C5H5ClN2O, 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 4-Chloro-2-methoxypyrimidine

INTERMEDIATE 62 4-(“3-Bromo-4-fluoro-lH”-pyrazol-l-vn-2-methoxypyrimidine To a solution of 3-bromo-4-fluoro-lH-pyrazole (500 mg, 3.03 mmol) in anhydrous DMSO (6 mL) was added NaH (133 mg, 3.13 mmol) at 0C. The mixture was stirred for 30 min at 0 C, followed by the addition of 4-chloro-2-methoxypyrimidine (438 mg, 3.03 mmol) in DMSO (2 mL). The resulting mixture was stirred at 90 C overnight. The mixture was cooled to room temperature, quenched with water (10 mL) and extracted with EtOAc (40 mL x 3). The organic layer was collected and dried over Na2S04. The solvent was removed in vacuo to give the crude product. This was purified by flash chromatography (ISCO Combiflash, 24g, Biotage Si column, ~60 mL/min, 100% hexanes 5 min, gradient to 100% EtOAc in hexanes 15 min) to afford 4-(3-bromo-4-fluoro-lH-pyrazol-l-yl)-2-methoxypyrimidine. LCMS calc. = 274.98; found = 274.90 (M+H)+.

With the rapid development of chemical substances, we look forward to future research findings about 51421-99-9.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MOCHIDA PHARMACEUTICAL CO., LTD.; SMITH, Cameron, James; TAN, John, Qiang; ZHANG, Ting; BALKOVEC, James; GREENLEE, William, John; GUO, Liangqin; XU, Jiayi; CHEN, Yi-heng; CHEN, Yili; CHACKALAMANNIL, Samuel; HIRABAYASHI, Tomokazu; NAGASUE, Hiroshi; OGAWA, Kouki; WO2014/120346; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 149849-92-3, 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. 149849-92-3, name is 2-Chloropyrimidine-4-carboxylic acid, molecular formula is C5H3ClN2O2, 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.

A mixture of compound IB (309 mg, 1 mmol), 2-chloropyrimidine-4- carboxylic acid (134.5 mg, 1 mmol) cesium carbonate (975 mg, 3 mmol) in 2 ml of DMSO was heated to 60 0C for 6 h. The product was poured into water and precipitated out of solution and was collected by filtration. The crude material was chromatographed (SiO2, 20 % methanol in dichloromethane) to afford 37 as a white powder: LCMS (97 % purity); retention time = 8.70 min, 432.0 [M + H]; 1H NMR (300 MHz, DMSO): 8.60 (IH, d), 8.25 (IH, d), 7.80 (IH, m), 7.60 (IH, d), 7.45 (IH, d), 7.1-7.2 (2H, m), 7.0 (IH, t), 6.75 (IH, d), 5.25 (2H, s), 3.95 (2H, t), 2.85 (2H, t).

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 149849-92-3, 2-Chloropyrimidine-4-carboxylic acid.

Reference:
Patent; GENENTECH, INC.; THE WALTER AND ELIZA HALL INSTITUTE OF MEDICAL RESEARCH; ABBOTT LABORATORIES; BAELL, Jonathon, Bayldon; BUI, Chinh, Thien; COLMAN, Peter; CZABOTAR, Peter; DUDLEY, Danette, A.; FAIRBROTHER, Wayne, J.; FLYGARE, John, A.; LASSENE, Guillaume, Laurent; NDUBAKU, Chudi; NIKOLAKOPOULOS, George; SLEEBS, Brad, Edmund; SMITH, Brian, John; WATSON, Keith, Geoffrey; ELMORE, Steven, W.; HASVOLD, Lisa, A.; PETROS, Andrew, M.; SOUERS, Andrew, J.; TAO, Zhi-Fu; WANG, Le; WANG, Xilu; DESHAYES, Kurt; WO2010/80503; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 64224-60-8, 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. 64224-60-8, name is 5-Bromo-4-pyrimidinecarboxylic acid. A new synthetic method of this compound is introduced below.

S-bromopyrimidine^-carboxylic acid (prepared according to the procedure described in U.S patent 4,110,450) (1.0 eq, 6.14 g, 30.2 mmol) was suspended in CH2Cl2 (100 ml). Oxalylchloride (1.1 eq, 2.9 ml, 33.0 mmol) was added followed by 2 drops of DMF. The mixture was stirred at room temperature overnight and the volatiles were removed in vacuo. The residue was taken in MeOH (50 ml) and heated. After evaporation of MeOH in vacuo the compound was dissolved in CH2Cl2 and poured on a prepacked silica gel column. The material was eluted using 20% Ethyl acetate in hexanes. Evaporation of the solvent provided methyl-5- bromopyrimidine-4-carboxylate as a light orange crystalline solid (2.54 g, 39% yield). LCMS (ES): 95% pure, m/z 217 [M]+; 219 [M+2]+; 1H NMR (CDCl3, 400 MHz) delta 4.04 (s, 3H), 9.02 (s, IH), 9.21 (s, IH) ppm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,64224-60-8, 5-Bromo-4-pyrimidinecarboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; CYLENE PHARMACEUTICALS, INC.; WO2008/28168; (2008); A2;,
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. 945950-37-8, name is 4-Methyl-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C7H7N3

Sten 6: To a stirred solution of (3R,3aS,6aR)-6.-((3-bromo-2-((4-methoxvbenzvl)amino)quinoiin-7-vi)nelhyi)hexahydro-211.-cyciopenta[h]furan-2,3,3a.-trioi (250 rng, 0.486 mmoi) in dry MeCN(9 rnL) was added tributviphosphine (176 ing, 0.869 rnmoi), followed by (E)-diazene-J.2-divlhis(piperi din-i -ylmethanone) (206 111g. 0815 mrnoi) at room temperature. The reactionmixture was stirred at room temperature for I h. and the solution was used directly in the nextstep without characterization; Step 7: To a stirred solution of 4-methyF-7I-Ipyrro1o [2, 3dj pyrimidine (129 mg, 0.970 mniol) in dry DMF (6 mL) was added sodium hydride (60% dispersion in mineral oil) (58.2 111g. 1.46 mmoi) at 0 C. The suspension was stirred at room temperature for 30 minutes, The suspensionwas transferred to the solution from the previous step containing the epoxide intermediate via syringe, and the resulting mixture was stirred at room temperature for 2 h. The reaction mixture was quenched with saturated aqueous ammonium chloride (30 mL) and extracted with EtOAc (40 mL 3). The combined organic layers were washed with brine (40 mL), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure.The residue was purified by Preparative TLC (MeOH/DCM) to afford (2R,3R,3aS,6aR)-6-(3- bromo-2(rnethoxyhenzyi)amino)quinolin-7-yl)methvi)-2-?4-methyi7H-pyrroio[2,3- d]pyrirnidinT-yi)hexahydro-3aWcyclopenta[hfuran-3, 3a-diol. MS: 630/632 (M+ 1/M+3). ?H NMR (40() M1-lz, DMSO-d6) oe 8.69 (s, 11-1), 8.32 (d, J= 6.0 Hz, IH), 8.02 (s, 1H), 7.54 (d, J= 8.2 Hz, 1H), 7.33 (d, J= 8.4 Hz, 2H), 7.14 -7.04 (rn, 3H), 6.91 -6.80 (m, 4H), 6.03(d, J 8.1Hz, 1H), 5.30 (d, J= 7.0 Hz, 1H), 5.12 (s, 1H), -4.61 (d, J= 6.2 Hz, 2H), 4.22 (t. J 7.6 Hz, 1H),4.04 (d, J == 6.6 Hz. 11-1), 3.72 (s, 31-1), 2.83 (dd, J: 13.7, 7.2 Hz, 11-1), 2.69(s. 31-1). 2.65 (s, 11-1),2,37 -2.22 (m, 11:1), 1.99- 1.93 (mn, 1H). 1,55 (d, J= 6.5 Flz. 2H).

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, 945950-37-8, 4-Methyl-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; IDENIX PHARMACEUTICALS LLC; MACHACEK, Michelle; WITTER, David; GIBEAU, Craig; HUANG, Chunhui; KAWAMURA, Shuhei; SLOMAN, David, L.; SILIPHAIVANH, Phieng; QUIROZ, Ryan; WAN, Murray; SCHNEIDER, Sebastian; YEUNG, Charles, S.; REUTERSHAN, Michael, H.; HENDERSON, Timothy, J.; PAPARIN, Jean-Laurent; RAHALI, Houcine; HUGHES, Jonathan, M., E.; SANYAL, Sulagna; YE, Yingchun; CANDITO, David, A.; FIER, Patrick, S.; SILVERMAN, Steven, M.; (277 pag.)WO2020/33288; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 4359-87-9, 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. 4359-87-9, name is 2,4,6-Trichloro-5-nitropyrimidine. A new synthetic method of this compound is introduced below.

Reference Example 1: N,N-dibenzyl-N’-tert-butyl-2-chloro-5-nitropyrimidine-4,6-diamine To 2,4,6-trichloro-5-nitropyrimidine (, 22.8 g) in methylene chloride(l 70 mL), a solution of tert-butylamine (7.3 g) in methylene chloride (30 mL) was slowly added dropwise at 0 C. To the reaction mixture, diisopropylethylamine (17.3 mL) was slowly added dropwise at 0 C. The reaction mixture was stirred at 0 C for 60 minutes. To the reaction mixture, water was poured and the reaction mixture was extracted with methylene chloride. The obtained organic layer was washed with a saturated saline solution, and was dried over sodium sulfate, and thereafter, was concentrated under a reduced pressure. 12.7 g of the obtained intermediate (27.8 g) was dissolved in methylene chloride (170 mL). To the solution, a solution of dibenzylamine (19.2 mL) in methylene chloride (30 mL) was added dropwise at 0 C. To the reaction mixture, diisopropylethylamine (17.3 mL) was added dropwise at 0 C. The reaction mixture was stirred at 0 C for 60 minutes. To the reaction mixture, water was poured and the reaction mixture was extracted with methylene chloride. The obtained organic layer was washed with a saturated saline solution, and was dried over sodium sulfate, and thereafter, was concentrated under a reduced pressure. The remaining intermediate (15.09 g) was similarly reacted. The obtained crude product was purified by silica gel column chromatography to give the title compound (27.2 g) having the following physical properties. TLC: Rf 0.45 (hexane: ethyl acetate = 9 : 1); 1H-NMR (CDCl3): delta1.51, 4.52, 7.06-7.14, 7.23-7.38, 8.41.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4359-87-9, its application will become more common.

Reference:
Patent; Ono Pharmaceutical Co., Ltd.; YAMAMOTO, Shingo; KURONO, Masakuni; YOSHIDA, Atsushi; HOTTA, Shingo; (53 pag.)EP3560926; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 947533-45-1, 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 947533-45-1, name is 2-bromo-5-fluoropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Step 2: Intermediate 4033A (100 mg, 0.180 mmol), 2-bromo-5-fluoropyrimidine (Frontier) (48 mg, 0.27 mmol, 1 .5 eq), potassium carbonate (87 mg, 0.63 mmol, 3.5 eq) and bis(tri-t- butylphosphine)palladium (0) (18 mg, 0.036 mmol, 0.20 eq) are charged in a microwave vial and DMF (1 .5 ml.) and water (0.50 ml.) are added. The vial is purged with argon, sealed and warmed in a microwave oven at 125 C for 10 min. The reaction mixture is filtered and purified by preparative HPLC to provide compound 4033 (tR: 1 .92, (M+H)+: 539.3/541 .3).

According to the analysis of related databases, 947533-45-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FADER, Lee; LEPAGE, Olivier; BAILEY, Murray; BEAULIEU, Pierre Louis; BILODEAU, Francois; CARSON, Rebekah; GIROUX, Andre; GODBOUT, Cedrickx; MOREAU, Benoit; NAUD, Julie; PARISIEN, Mathieu; POIRIER, Martin; POIRIER, Maude; SURPRENANT, Simon; THIBEAULT, Carl; WO2013/152063; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1146629-75-5, 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 1146629-75-5, name is (4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate. This compound has unique chemical properties. The synthetic route is as follows.

Step 16: tert-Butyl 4-(6-aminopyrimidin-4-yI)-2-(5-chloro-2-methylphenyl)-1 H-pyrrole-1 -carboxylate (XXI) The crude tert-butyl 2-(5-chloro-2-methylphenyl)-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-pyrrole-1 -carboxylate (392 mg, 0.94 mmol), Na2003 (250 mg, 2.36 mmol), PdC2(dppf) (77 mg, 0.094 mmol) and 6-iodopyrimidin-4-amine (311 mg, 1.41 mmol) were degassed and purged with argon and suspended in degassed 1,4-dioxane (3 mL) and water (1 mL). The reaction mixture was heated to 110 00 (oil bath temperature) for 2 h. Thesolution was diluted with EtOAc and washed with water. After drying over anhydrous Na2SO4, the organic layer was evaporated. The crude was purified by chromatography on silica gel (hexane/EtOAc 8:2) providing the title compound (220 mg, 58%).1H NMR (600 MHz, DMSQ-d6) 8.55 (s, 1 H), 7.79 (s, 1H), 7.41 (d, 1H), 7.29 (d, 1H), 7.16 (m, 1H), 6.98 (s, 1H),6.66 (s, 1H), 2.30 (s, 3H), 1.44 (s, 9H).According to this procedure, but starting from tert-butyl 2-(5-chloro-2-ethyl phenyl)-4-iodo-1 H-pyrrole-1 -carboxylate, using 4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl 2,2-dimethylpropanoate instead of 6-iodopyrimidin-4-amine in the step 16 and removing the 2,2-dimethylpropanoyl protecting group with LiOH.H20 in THE/water at roomtemperature, the following compound was prepared:2-(5-Chloro-2-ethylphenyl)-N-methyl-4-(7H-pyrrolo[2,3-d]pyrimidin-4-yI)-1 H-pyrrole-1 -carboxamide (compd185)ESI (+) MS: m/z 380 (MW).

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 1146629-75-5, (4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate.

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

Electric Literature of 2915-16-4, 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. 2915-16-4, name is 2-Chloro-4,6-diphenylpyrimidine. A new synthetic method of this compound is introduced below.

Under a nitrogen atmosphere, 50g (187mmol) the compound 2-chloro-4,6-diphenyl pyrimidine was dissolved in 1LTHF added thereto 37g (155mmol) (3- bromophenyl) borate, and 2.1g (1.8mmol) tetrakis (triphenylphosphine) palladium, and the mixture was stirred. Subsequently, thereto added 64g (467mmol) of potassium carbonate saturated aqueous solution, and the resulting mixture was heated at reflux for 80 12 hours. When the reaction was completed, water was added to the reaction solution, and the mixture was extracted with dichloromethane ((the DCM), followed by removal of water and dried over anhydrous MgSO4 filtered and concentrated under reduced pressure. The residue obtained was separated via flash column and chromatography to obtain 66g (92%) compound I-17.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2915-16-4, 2-Chloro-4,6-diphenylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Samsung SDI Co., Ltd.; Jin, Chengxuan; Jin, Yongquan; Liu, Dongwan; Jin, Lunhuan; Liu, Yinshan; Zheng, Chengxian; (85 pag.)CN105566200; (2016); A;,
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. 28969-60-0, name is 2,5,6-Trichloropyrimidin-4-amine, molecular formula is C4H2Cl3N3, 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. Formula: C4H2Cl3N3

EXAMPLE 1 This example illustrates the preparation of 4(2,3,5,6-tetrafluoro-4-trifluoromethylanilino)2,5,6-trichloropyrimidine (Comound No. 6 of Table I) having the formula: SPC1 4-Amino-2,5,6-trichloropyrimidine (1.98 g) was dissolved in dry dimethylformamide (25 cc) and the solution added dropwise to a stirred suspension of sodium hydride (0.5 g) in dry dimethylformamide (25 cc) under a nitrogen atmosphere at 0C. When the addition was complete and evolution of hydrogen had ceased a solution of octafluorotoluene (2.4 g) in dry dimethylformamide (15 cc) was added dropwise to the mixture at 0C. When this addition was complete the mixture was stirred for 30 minutes, and the temperature allowed to rise to 21C. The mixture was then poured into a mixture of iced water and salt (400 cc) and acidified with dilute hydrochloric acid. The gummy precipitate which was formed slowly hardened on standing (18 hours) and was twice recrystallized from a mixture of methylene chloride and petroleum ether (boiling range 40-60C) to yield 4(2,3,5,6-tetrafluoro-4-trifluoromethylanilino)-2,5,6-trichloropyrimidine, having a melting point of 152.4 to 153C.

With the rapid development of chemical substances, we look forward to future research findings about 28969-60-0.

Reference:
Patent; Imperial Chemical Industries Limited; US3974276; (1976); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 49845-33-2, 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. 49845-33-2, name is 2,4-Dichloro-5-nitropyrimidine. A new synthetic method of this compound is introduced below.

2,4-dichloro-5-nitropyrimidine(3g, 15.4 mmol) was dissolved in tetrahydrofuran(52 mL) and 2N methylamine (15.4 mL) dissolved in tetrahydrofuran was slowly added at -78°C. The resulting solution was stirred for 10 minutes and then further stirred for 50 minutes at room temperature. The resulting solution was concentrated under reduced pressure, diluted with ethyl acetate(50 mL), and washed with water (30 mL) and saline (30 mL). The resultant was dehydrated with anhydrous sodium sulfate, concentrated under reduced pressure, and applied to column chromatography (EA : Hex = 20 : 1 ? 5 : 1) to yield Compound XL (925 mg (32percent)). 1H NMR (600MHz, chloroform-d1) delta 9.05(s, 1H), 8.41(br, 1H), 3.23 (d, J = 4.8Hz, 3H),

At the same time, in my other blogs, there are other synthetic methods of this type of compound,49845-33-2, 2,4-Dichloro-5-nitropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; LegoChem Biosciences, Inc.; CHO, Young Lag; YUN, Joung Yul; PARK, Chul Soon; CHAE, Sang Eun; LEE, Hyang Sook; OH, Kyuman; HEO, Hye Jin; KANG, Dae Hyuck; YANG, Young Jae; KWON, Hyun Jin; PARK, Tae Kyo; WOO, Sung Ho; KIM, Yong Zu; EP2706062; (2014); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia