Pyrimidines

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;,
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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;,
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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;,
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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;,
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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;,
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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;,
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Application of 29274-24-6 ,Some common heterocyclic compound, 29274-24-6, molecular formula is C6H4ClN3, 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 8; 5-Chloropyrazolo [1, 5-a] pyrimidine (100 mg) andN-iodosuccinimide (161 mg) in N, N-dimethylformamide (ImI) was stirred at ambient temperature for 4 hours. The reaction mixture was poured into a mixture of 10% sodium thiosulfate aqueous solution and chloroform. Then the organic layer was washed with saturated NaHCU3 aqueous solution, water, brine, dried over magnesium sulfate, and evaporated in vacuo. Resulting precipitates were collected by filtration and washed with diisopropyl ether to give 5-chloro-3-iodopyrazolo [ 1, 5-a] pyrimidine as an brown solid (180 mg) .1H-NMR(DMSO-d6)delta:7.42 ( IH, d, J=9.5Hz) , 7.97 ( IH, s) , 8.23 ( IH, d, J=9.2Hz) . MS:279 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,29274-24-6, its application will become more common.

Reference:
Patent; ASTELLAS PHARMA INC.; WO2007/13673; (2007); A1;,
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Adding a certain compound to certain chemical reactions, such as: 591-55-9, 5-Aminopyrimidine, 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

[00160] Step 1: Synthesis of tert-butyl 2-(tert-butyldimethylsilyloxy)-3-(3-(l-isopropyl- 4- (pyrimidin-5-ylamino)-lH-pyrazolo[3,4-b]pyridin-6-yl)-5-methoxyphenoxy) propyl(methyl)carbamate. A mixture of tert-butyl 2-(tert-butyldimethylsilyloxy)-3-(3-(7- chloro-3-isopropyl- pyrazolo[l,5-a]pyrimidin-5-yl)-5-methoxyphenoxy)-propyl(methyl)- carbamate (600 mg, 0.97 mmol); pyrimidin-5-amine (139 mg, 1.46 mmol); Pd2(dba)3 (136 mg, 0.194 mmol); BINAP (121 mg, 0.19 mmol) and NaOt-Bu (286 mg, 2.31 mmol) in 15 mL of dioxane was heated at 100 C under N2 for 14h. After cooling down to room temperature, water (30 mL) was added and the mixture was extracted with EtOAc (30 mL X 3). The organic phase was concentrated and the residue was purified by preparative TLC on silica gel developed with DCM/MeOH = 20: 1 to afford 2-(tert-butyldimethylsilyloxy)-3-(3-(l- isopropyl-4-(pyrimidin-5-ylamino)- lH- pyrazolo[3,4-b]pyridin-6-yl)-5- methoxyphenoxy)propyl (methyl)carbamate (190 mg, 29 % yield) as a pale yellow solid. ESI-LCMS (m/z): 678.3 [M+l]+.

The synthetic route of 591-55-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EPIZYME, INC.; CHESWORTH, Richard; MORADEL, Oscar Miguel; SHAPIRO, Gideon; DUNCAN, Kenneth W.; MITCHELL, Lorna Helen; JIN, Lei; BABINE, Robert E.; WO2014/144455; (2014); A1;,
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Synthetic Route of 2915-16-4, 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.2915-16-4, name is 2-Chloro-4,6-diphenylpyrimidine, molecular formula is C16H11ClN2, molecular weight is 266.73, as common compound, the synthetic route is as follows.

TP2 is further reacted with 2-chloro-4,6-diphenylpyrimidine (1.0 equivalents, CAS: 2915-16-4), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3 (0.03 equivalents; CAS 51364-51 -3), Tricyclohexylphosphine (PCy3; 0.07 equivalents, CAS 2622-14-2) and potassium phosphate tribasic (K3PO4, 1 .7 equivalents). The reaction mixture is stirred under nitrogen atmosphere in a dioxane/toluen e/water (6/1/1 ) mixture at 100 C overnight. After cooling down to room temperature (RT) the reaction mixture is extracted with DCM/brine. The organic phases are collected, washed with brine and dried over MgS04. The organic solvent is removed, the crude product was washed with cyclohexane and recrystallized from EtOH (Yield: 98%).

Statistics shows that 2915-16-4 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-4,6-diphenylpyrimidine.

Reference:
Patent; CYNORA GMBH; SZAFRANOWSKA, Barbara; PINGEL, Patrick; BERGMANN, Larissa; AMBROSEK, David; KASPAREK, Christian; (0 pag.)WO2019/162332; (2019); A1;,
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Electric Literature of 1209459-16-4, Adding some certain compound to certain chemical reactions, such as: 1209459-16-4, name is 2-Bromopyrimidine-4-carbonitrile,molecular formula is C5H2BrN3, 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 1209459-16-4.

Example 11. Preparation of (3S)-tert-butyI 3-((l-(2-chIorophenyl)-2-((3,3- difluorocyclobutyl) amino)-2-oxoethyl)(3,5-difluorophenyl)carbamoyl)-4-(4- cyanopyrimid -2-yl)-5-oxopiperazine-l-carboxylate (racemic) – Compound 98 A mixture of (3S)-tert-butyl3-((l -(2-chlorophenyl)-2-((3,3-difluorocyclobutyl)amino)-2-oxoethyl) (3,5-difluorophenyl)carbamoyl)-5-oxopiperazine-l-carboxylate (200 mg, 0.326 mmol), 2- bromopyrimidine-4-carbonitrile (0.489 mmol), Pd2(dba)3 (30.2 mg, 0.0323 mmol), XantPhos (19.1 mg, 0.03 mmol) and Cs2C03 (148.7 mg, 0.46 mmol) in 1,4-dioxane (10 mL) was stirred at 80 C for 3 hr under N2. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated and the residue was purified by a standard method to afford the desired product. NMR (400 MHz, CDC13): delta 8.97 (d, J= 4.3 Hz, 1H), 7.85-7.55 (d, 1H), 7.51-7.39 (m, 2H), 7.25 (t, J= 7.6 Hz, 1H), 7.13-6.26 (m, 6H), 5.91 (d, J= 7.6 Hz, 1H), 4.92-4.08 (m, 5H), 3.38 (t,J= 14.9 Hz, 1H), 3.02 (s, 2H), 2.83-2.22 (d, 2H), 1.61 (s, 9H). MS : 716.1 (M+l)+.

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. 1209459-16-4, 2-Bromopyrimidine-4-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; LEMIEUX, Rene M.; POPOVICI-MULLER, Janeta; TRAVINS, Jeremy M.; CAI, Zhenwei; CUI, Dawei; ZHOU, Ding; WO2015/10297; (2015); A1;,
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