Day: March 10, 2021

Reference of 799842-07-2, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 799842-07-2 as follows.

General procedure: Aq 1 M NaOH (9 mL, 1.5 equiv) was added to a stirred MeOH (20mL) solution of the appropriate aromatic thiol (7.2 mmol, 1.2equiv). The solution was stirred at r.t. for 15 min and then the heterocyclicalkyl bromide 2 or 3 (6 mmol, 1 equiv) was added. When rosuvastatin moiety bromides 2 were used, THF (10 mL) was also added to the mixture to improve solubility. After 18 h, the solvent was evaporated, the residue was dissolved in CH2Cl2 (50 mL), and washed with H2O (100 mL). The aqueous phase was additionally extracted with CH2Cl2 (2 ¡Á 25 mL). The combined organic phases were dried (MgSO4) and the solvent was evaporated. The residuewas recrystallized and the isolated product was dried in vacuumovernight at 60 C below 50 mbar to give the pure sulfide heterocyclic precursor 4 or 5 in 75-97% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,799842-07-2, its application will become more common.

Reference:
Article; Fabris, Jan; ?asar, Zdenko; Smilovi?, Ivana Gazi?; ?rnugelj, Martin; Synthesis; vol. 46; 17; (2014); p. 2333 – 2346;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 7752-82-1 , The common heterocyclic compound, 7752-82-1, name is 5-Bromopyrimidin-2-amine, molecular formula is C4H4BrN3, 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.

To a solution of 2-amino pyridine (30 g, 0.31 mol) in DME (120 mL) was added chloro acetone (40.5 mL, 0.47 mol) at room temperature. The reaction mixture was heated to reflux, and then stirred for 48 hours. The volatiles were concentrated under reduced pressure. Then the residue was purified by column chromatography eluting with 1% MeOH/DCM to afford Int-2 (20 g, 48%) as a liquid. Mass (m/z): 133 [M++1]. 1H NMR (200 MHz, dmso-d6): delta8.05 (d, J=8.2 Hz, 1H), 7.35 (s, 1H), 7.1 (t, J=6.8 Hz, 1H), 6.7 (t, J=6.8 Hz, 1H), 6.5 (d, J=8.2 Hz, 1H), 2.45 (s, 3H). To a solution of Int-2 (10 g, 76.7 mmol) in acetonitrile (50 mL) was added N-iodo succinamide (20.4 g, 80 mmol) portion wise at room temperature and then stirred for 48 hours. The precipitated solid was filtered off. The crude material was re-crystallized from ethyl acetate/water to afford Int-3 (9 g, 49%) as solid. Mass (m/z): 259 [M++1]. 1H NMR (200 MHz, dmso-d6): delta 8.22 (d, J=8 Hz, 1H), 7.47 (d, J=7.2 Hz, 1H), 7.29 (t, J=7.0 Hz, 1H), 2.35 (s, 3H). To a solution of Int-3 (6.0 g, 29.2 mmol) in IPA-H2O (75 mL, 2:1) was added PdCl2(dppf).DCM (4.7 g, 5.8 mmol), followed by the addition of tert-butyl amine (3.1 g, 43.8 mmol) at room temperature and the resulting reaction mixture was degassed for 15 minutes. Then Int-4 (2.9 g, 18.6 mmol) was added to the reaction mixture at room temperature. The reaction mixture was heated to 100 C. and then stirred for 16 hours. The reaction mixture was diluted with water (100 mL), extracted with EtOAc (3¡Á100 mL), washed with water, brine and dried over anhydrous Na2SO4. The organic layer was concentrated under reduced pressure. The crude material was purified by column chromatography eluting with 1% MeOH/DCM to afford Int-5 (1.6 g, 28%). Mass (m/z): 244 [M++1]. 1H NMR (200 MHz, dmso-d6): delta 8.51 (t, J=5 Hz, 2H), 7.71 (s, 1H), 7.63-7.55 (m, 2H), 7.34 (t, J=7 Hz, 1H), 6.94 (t, J=7 Hz, 1H), 2.43 (s, 3H). To a stirred mixture of 5-bromo 2-aminopyrimidine (8 g, 45.97 mmol) in MeOH-CH3CN (200 mL) in a steel bomb were added Pd(CH3CN)2Cl (2.38 g, 9.19 mmol), racemic-BINAP (5.7 g, 9.19 mmol), DIPEA (10.4 mL, 53.7 mmol) at room temperature and then closed the steel vessel tightly. Then CO gas (100 psi) was purged into the steel bomb and the stirring was continued at 120 C. for 45 hours. The reaction mixture was allowed to room temperature. The reaction mixture was filtered through a pad of celite. The celite pad was washed with excess of methanol and the filtrate was concentrated under vacuum. The crude material was purified by column chromatography eluting with 0.75% MeOH/DCM to afford Int-6 (5 g, 71%) as solid. Mass (m/z): 154 [M++1]. 1H NMR (200 MHz, dmso-d6): delta 8.65 (s, 3H), 7.49 (brs, 2H), 3.58 (s, 3H) To a stirred mixture of Int-5 (3 g, 2.34 mmol) and Int-6 (1.8 g, 12.34 mmol) in 1,4-dioxane (90 mL) were added Pd(OAc)2 (279 mg, 1.23 mmol) and Xanthpos (710 mg, 1.23 mmol) followed by cesium carbonate (6 g, 18.5 mmol) at room temperature. The resulting mixture was degassed and stirred at reflux temperature for 30 hours. The reaction mixture was cooled to room temperature and then stirred for 15 minutes. The precipitated solids were filtered off, washed with water (2¡Á10 mL) and dried under vacuum. The crude material was purified by column chromatography eluting with 1.5% MeOH/DCM to afford Int-7 (0.6 g, 13.6%) as solid. Mass (m/z): 361.2 [M++1]. 1H NMR (500 MHz, dmso-d6): delta 10.76 (brs, 1H), 8.97 (s, 2H), 8.56 (d, J=7, 1H), 8.47 (d, J=5.5 Hz, 1H), 8.38 (s, 1H), 7.58 (d, J=9.5 Hz 1H), 7.34-7.29 (m, 2H), 6.99 (t, J=76 Hz, 1H), 3.84 (s, 3H), 2.46 (s, 3H). To a stirred solution of Int-7 (0.5 g, 1.38 mmol) in MeOH-CH3CN (1:2, 25 mL) was added aqueous NH2OH solution (15 mL) at 0 C. After being stirred for 20 minutes at the same temperature, NaOH (0.44 g, 11.10 mmol) in water (1 mL) was added drop wise to the reaction mixture at 0 C. The reaction mixture was warmed to room temperature and stirred for 2 days. The volatiles were concentrated under vacuum and the obtained residue was diluted with water and neutralized to about pH 7 with 2 N HCl at 0 C. The precipitated solids were filtered off, washed with water (2¡Á10 mL) and dried under vacuum to afford the title compound (0.4 g, 80%) as off-white solid. Mass (m/z): 362.1 [M++1]. 1H NMR (200 MHz, dmso-d6): delta 11.2 (bs, 1H), 10.5 (s, 1H), 9.12 (bs, 1H), 8.84 (s, 2H), 8.57 (d, J=7.0 Hz, 1H), 8.45 (d, J=5.0 Hz, 1H), 8.38 (s, 1H), 7.58 (d, J=9.0 Hz, 1H), 7.32 (t, J=7.5 Hz, 1H), 7.25 (d, J=4.0 Hz, 1H), 6.98 (d, J=7.0 Hz, 1H), 2.49 (s, 3H). 13C NMR (125 MHz, dmso-d6): delta 160.7, 157.1, 153.0, 148.7, 144.5, 142.3, 137.9, 125.2, 123.9, 118.8, 118.2, 117.0, 116.6, 112.7, 112.4, 14.3.

The synthetic route of 7752-82-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Melvin, JR., Lawrence S.; Graupe, Michael; Venkataramani, Chandrasekar; US2010/29638; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 4316-93-2, Adding some certain compound to certain chemical reactions, such as: 4316-93-2, name is 4,6-Dichloro-5-nitropyrimidine,molecular formula is C4HCl2N3O2, 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 4316-93-2.

6-Chloro-5-nitropyrimidin-4-amine[00161] A solution of 28% aqueous ammonium hydroxide (670 mL, 5.35 mol, 1.04 equiv) was added in a drop-wise fashion to a rapidly stirred solution of the 4,6-dichloro-5- nitropyrimidine solid (1000 g, 5.16 mol, 1.00 equiv) in diethyl ether (4000 mL) and methanol (670 mL). The addition was carried out over a period of 2 hours. Upon completion of addition, the resulting yellow solid was filtered off, washed with water and hexane, and dried under reduced pressure to give the title compound as a yellow solid (yield: 675 g). This crude solid was used in the next step without any further purification. NMR (400 MHz, DMSO- d6): delta 8.97 (s, 1H), 7.91 (broad s, 2H). MS (EI) for C4H3CIN4O2: 175 (MH+).

According to the analysis of related databases, 4316-93-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EXELIXIS, INC.; PATRICK, Kearney; WO2012/37226; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 171887-03-9, Adding some certain compound to certain chemical reactions, such as: 171887-03-9, name is N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide,molecular formula is C5H4Cl2N4O, 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 171887-03-9.

7-Chloro-3-r6-ri-hvdroxy-l-methylethyl1pyridine-2-ylmethyl)-3H-ri,2,31triazolor4.5- Patent; VERNALIS (R&D) LIMITED; WO2009/156737; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 289042-12-2, 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.289042-12-2, name is tert-Butyl 2-((4R,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate, molecular formula is C29H40FN3O6S, molecular weight is 577.71, as common compound, the synthetic route is as follows.

A mixture of BEM (5.0 g) and acetonitrile (35 ml) was stirred under an inert atmosphere at 40 C. 0.02M hydrochloric acid (9.5 ml) was added over 30 minutes to the resultant solution, maintaining the temperature at 35 C. to 42 C. The mixture was stirred at 40 C. for 3 hours then cooled to 25 C. 1.0M sodium hydroxide solution (9.5 ml) was added with stirring at 25 C. and the mixture was stirred for an additional one hour at 25 C. Sodium chloride (4.7 g) was added and the mixture was cooled to -5 C. over one hour. Sufficient of a solution of 1M hydrochloric acid (9.5 ml) and sodium chloride (2.4 g) was added at -5 C. to achieve a pH of 3.4 to 4.0 and the mixture stirred at this temperature for 5 minutes. The mixture was allowed to settle for 10 minutes at -5 C. to give two layers. The lower layer was separated and discarded. Acetonitrile (65 ml) at -5 C. was added to the remaining solution and the mixture was filtered through a filter agent. 40% methylamine solution in water (1.1 ml) was added at -5 C. and the mixture was warmed to 30 C. over 40 minutes and maintained at this temperature for 90 minutes. The mixture was then cooled to 0 C. over 40 minutes and maintained at this temperature for 90 minutes. The resultant solid was collected by filtration and washed with acetonitrile (2¡Á12 ml). The solid, which is the methylamine salt of the compound of formula IV (R1=MeNH3+), was dried under vacuum at 35 C. (3.87 g). 8% w/w aqueous sodium hydroxide (5.44 ml) was added to a stirred mixture of the methylamine salt (6.0 g) in degassed water (30 ml) at 20 C. and the mixture was stirred for one hour. The mixture was filtered and concentrated under reduced pressure at 40 C. until 24 ml of distillate collected. Water (24 ml) was added and the mixture again concentrated under reduced pressure at 40 C. until 24 ml of distillate collected. Water (30 ml) was added and a solution of calcium chloride dihydrate (1.03 g) in water (6 ml) was added dropwise at 20 C. The mixture was stirred for 45 minutes and the resultant solid filtered. The solid was washed with water (36 ml) and dried under vacuum at 40 C. to give the calcium salt of (E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl](3R,5S)-3,5-dihydroxyhept-6-enoic acid.

Statistics shows that 289042-12-2 is playing an increasingly important role. we look forward to future research findings about tert-Butyl 2-((4R,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate.

Reference:
Patent; Butters, Michael; Lenger, Steven Robert; Murray, Paul Michael; Snape, Evan William; US2008/207903; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 50593-92-5, name is 5-Bromo-2-(methylthio)pyrimidine-4-carboxylic acid. A new synthetic method of this compound is introduced below., Product Details of 50593-92-5

Acetyl chloride (6.26ml, 0.088mol) was added dropwise at 0-50C to methanol (100ml). The mixture was stirred at 0-50C for 5min. 5-Bromo-2- methylsulfanylpyrimidine-4-carboxylic acid (2Og, O.Odeltamol) was added in portions at 0-50C then the mixture was heated under reflux for Ih, during which time the slurry dissolved, then it was cooled to ambient temperature and poured into saturated aqueous sodium hydrogencarbonate solution (100ml). The product was extracted into dichloromethane (3xl00ml), the extracts were washed with water(100ml), dried (MgSO4) and evaporated in vacuo. The residual solid was crystallised from hexane to give 5-bromo-2-methylsulfanylpyrimidine-4-carboxylic acid methyl ester (12.27g) as an off white crystalline solid, m.pt. 67-700C; 250 MHz 1H-NMR (CDCl3) delta (ppm): 2.6 (s, 3H) (-SCH3), 4.05 (s, 3H) (-OCH3), 8.7 (s, IH) (ArH); m/z (M+H)+’ 249; HPLC purity 96%; HPLC retention time 1.58min.

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, 50593-92-5, 5-Bromo-2-(methylthio)pyrimidine-4-carboxylic acid.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2007/88014; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1194-21-4, 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.1194-21-4, name is 2-Amino-6-chloropyrimidin-4(3H)-one, molecular formula is C4H4ClN3O, molecular weight is 145.55, as common compound, the synthetic route is as follows.

6-Amino-4-chloropyrimidin-2(1H)-one (3, 200 mg, 0.84 mmol) and 2-methyl-5-nitroaniline (627 mg, 2.52 mmol) were heated at 170 C for 3 h. The mixture was then cooled to rt and diethyl ether was added. The mixture was sonicated for 5 min. The suspension was filtered, and the filter cake was dissolved in MeOH and purified by column chromatography (silica gel, dichloromethane/methanol 9:1 v/v) to afford 4 (128 mg, 60%) as a brown solid.

Statistics shows that 1194-21-4 is playing an increasingly important role. we look forward to future research findings about 2-Amino-6-chloropyrimidin-4(3H)-one.

Reference:
Article; Kim, Hee Jin; Oh, Chang-Hyun; Yoo, Kyung Ho; Bulletin of the Korean Chemical Society; vol. 34; 8; (2013); p. 2311 – 2316;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 6972-27-6, 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. 6972-27-6, name is 6-Chloro-1,3-dimethylpyrimidine-2,4(1H,3H)-dione. A new synthetic method of this compound is introduced below.

General procedure: A mixture of (18a) (69 mg, 0.176 mmol), 6-chloro-1,3-dimethylpyrimidine-2,4(1H,3H)-dione (61 mg, 0.35 mmol) and diisopropylethylamine (0.152 mL, 0.880 mmol) in isopropyl alcohol (0.5 mL) was heated at 80 C for 7 h. The reaction mixture was diluted with ethyl acetate, washed with satd NaHCO3 and brine, dried over NaSO4, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane, and then MeOH/CHCl3) to give methyl 2-(11-(3-(4-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)piperazin-1-yl)propylidene)-6,11-dihydrodibenzo[b,e]oxepin-2-yl)acetate (87 mg, 93% yield) as amorphous.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6972-27-6, its application will become more common.

Reference:
Article; Kubota, Katsumi; Kurebayashi, Hirotaka; Miyachi, Hirotaka; Tobe, Masanori; Onishi, Masako; Isobe, Yoshiaki; Bioorganic and Medicinal Chemistry; vol. 19; 9; (2011); p. 3005 – 3021;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 3934-20-1, Adding some certain compound to certain chemical reactions, such as: 3934-20-1, name is 2,4-Dichloropyrimidine,molecular formula is C4H2Cl2N2, 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 3934-20-1.

Into a 50-mL round-bottom flask, was placed 2,4-dichloropyrimidine (1.1 g, 7.38 mmol, 1.00 equiv.), methanamine hydrochloride (498 mg, 7.38 mmol, 1.00 equiv.), potassium carbonate (3.07 g, 22.21 mmol, 3.00 equiv.), N,N-dimethylformamide (10 mL). The resulting solution was stirred for 18 h at 20 C. The resulting solution was diluted with 60 mL of H2O. The resulting solution was extracted with 3×80 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 3×100 mL of brine. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/2). This resulted in 0.67 g (63%) of 2-chloro-N- methylpyrimidin-4-amine as a white solid.

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. 3934-20-1, 2,4-Dichloropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EPIZYME, INC.; CAMPBELL, John Emmerson; DUNCAN, Kenneth William; FOLEY, Megan Alene; HARVEY, Darren Martin; KUNTZ, Kevin Wayne; MILLS, James Edward John; MUNCHHOF, Michael John; (586 pag.)WO2017/181177; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 35144-22-0, name is 4,6-Dimethyl-2-methylsulfonylpyrimidine. A new synthetic method of this compound is introduced below., Safety of 4,6-Dimethyl-2-methylsulfonylpyrimidine

Example 35 76 mg of 5-isopropyl-N-[6-(4-(4,6-dimethyl-2-pyrimidinyloxy)-2-butynyloxy)-5-(o-methoxyphenoxy)-2-methyl-4-pyrimidinyl]-2-pyridine sulfonamide was obtained as a colourless foam starting from 80 mg of 5-isopropyl-N-[6-(4-hydroxy-2-butynyloxy)-5-(o-methoxyphenoxy)-2-methyl-4-pyrimidinyl]-2-pyridine sulfonamide (Example 7d) and 75 mg of 4,6-dimethyl-2-methylsulfonylpyrimidine following the procedure given in Example 17. LC-MS: tR=5.51 min, [M+1]+=605.35, [M-1]-=603.43.

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, 35144-22-0, 4,6-Dimethyl-2-methylsulfonylpyrimidine.

Reference:
Patent; Bolli, Martin; Boss, Christoph; Clozel, Martine; Fischli, Walter; US2003/87920; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia