Tag: M.W:100-200

Synthetic Route of 504-17-6 , The common heterocyclic compound, 504-17-6, name is 4,6-Dihydroxy-2-mercaptopyrimidine, molecular formula is C4H4N2O2S, 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.

General procedure: Nano-sawdust-OSO3H (0.02 g) was added to a stirred mixture of the aromatic aldehyde (1 mmol), malononitrile (1 mmol) and barbituric acid or thiobarbituric acid (1 mmol) in EtOH (5 mL). The materials were mixed and refluxed for the appropriate time. The progress of the reaction was followed by TLC (n-hexane:ethyl acetate 3:1). After completion of the reaction, the mixture was filtered to remove the catalyst. After evaporation of the solvent, the crude product was re-crystallized from hot ethanol to obtain the pure compound.

The synthetic route of 504-17-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sadeghi; Bouslik; Shishehbore; Journal of the Iranian Chemical Society; vol. 12; 10; (2015); p. 1801 – 1808;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 1780-26-3, 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.1780-26-3, name is 2-Methyl-4,6-dichloropyrimidine, molecular formula is C5H4Cl2N2, molecular weight is 163.0047, as common compound, the synthetic route is as follows.

Example 127. 2-[4-(6-Chloro-2-methvl-pyrimidin-4-vl)-piperaziii-l-vll-ethano?71); [0307] To a solution of 4,6-dichloro-2-methyl-pyrimidine (5.0 g, 31 mmol) and 2- pirhoerazin-1-yl-ethanol (2.7 g, 21 mmol) in dioxane (25 mL) was added DEPEA (3.0 mL, 17 mmol). The mixture was heated at reflux for 16 h. The mixture was allowed to cool to room temperature and poured into water. The resulting aqueous layer was extracted with EtOAc and the combined organic layers washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated and the residue purified by flash chromatography on silica gel (5-10% MeOH/DCM) to afford the title compound as a brown liquid (2.1 g, 39%). MS (ES+): m/z 257 (M+H)+.

Statistics shows that 1780-26-3 is playing an increasingly important role. we look forward to future research findings about 2-Methyl-4,6-dichloropyrimidine.

Reference:
Patent; TARGEGEN, INC.; WO2006/101977; (2006); A2;,
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.24391-41-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile, molecular formula is C7H3ClN4, molecular weight is 178.58, as common compound, the synthetic route is as follows.Quality Control of 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Step 13-3 (5)-4-(2-(7-fiuoro-4-oxo-3,4-dihydropyrrolo[l,2-f][l,2,4]triazin-2-yl) pyrrolidin- 1 -yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (106) Compound 106 A mixture of 13b (0.16 mmol), 4-chloro-7H-pyrrolo[2,3-d]pyrimidine- 5-carbonitrile (28 mg, 0.16 mmol) and TEA (0.08 mL, 0.58 mmol) in n-BuOH (5 mL) was stirred at reflux for 2 hours. The reaction mixture was concentrated and purified by flash column chromatography eluting with MeOH/water to afford Compound 106 as a white solid (27 mg, yield: 62%). MS (m/z): 364.7 (M+H)+. 1H NMR (400 MHz, DMSO-d6) delta: 13.07-12.72 (m, 1H), 11.76 (s, 1H), 8.30 (s, 1H), 8.13 (s, 1H), 6.81-6.73 (m, 1H), 6.31-6.09 (m, 1H), 5.15-5.07 (m, 1H), 4.32-4.24 (m, 1H), 3.96-3.92 (m, 1H), 2.40-2.30 (m, 1H), 2.18-2.02 (m, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,24391-41-1, 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-Guo; DAI, Guangxiu; XIAO, Kun; JIA, Hong; VENABLE, Jennifer Diane; BEMBENEK, Scott Damian; WO2014/15675; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 939986-65-9, 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.939986-65-9, name is 6-Chloropyrimidine-4-carbonitrile, molecular formula is C5H2ClN3, molecular weight is 139.5425, as common compound, the synthetic route is as follows.

To a stirred solution of compound 3 (55 mg, 0.29 mmol) inN-methyl-2-pyrrolidone (5 mL) at RT, were added 6-chloropyrimidine-4-carbonitrile (60 mg, 0.43 mmol) and Cs2CO3 (189 mg, 0.58 mmol), and the mixture was stirred for 12 h. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc (2 x 15 mL). The combined organic extracts were washed with brine (10 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude was purified via trituration with n-pentane (2 x 2 mL) to afford compound 4 (55 mg, 65%) as pale brown solid. ?HNMR (500MHz, DMSO-d6): 8.85 (d, J 0.9 Hz, 1H), 8.00 (d, J= 0.9 Hz, 1H), 7.77 (d, J= 3.2 Hz, 1H), 7.56 (d, J 8.4 Hz, 1H), 7.23 (t, J 8.0 Hz, 1H), 6.95 (d, J= 7.5 Hz, 1H), 6.32 (d, J= 3.2 Hz, 1H), 5.86-5.78 (m, 1H), 5.05 (t, J 7.4 Hz, 2H), 4.95 (t, J= 6.7 Hz, 2H); LCMS Mass: 293.0 (M+1).

The chemical industry reduces the impact on the environment during synthesis 939986-65-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PHARMAKEA, INC.; ROWBOTTOM, Martin, W.; HUTCHINSON, John, Howard; (185 pag.)WO2017/3862; (2017); A1;,
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

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

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

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

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

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