Pyrimidines

Application of 211244-81-4, 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. 211244-81-4, name is 2-(Methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one, molecular formula is C8H7N3OS, 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.

EXAMPLE 52-MethanesuIfinyl-8H-pyrido[2,3-d]pyrimidin-7-one; To a suspension of 2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (WO 9833798 A2, 5.0 g, 25.9 mmol) in CH2Cl2 (100 mL), CHCl3 (50 mL) and MeOH (10 mL, the starting material still did not dissolve) was added the oxaziridine (8.11 g, 31.05 mmol, 1.2 equiv) as a solid. The reaction became homogenous after 3 h and was stirred overnight at RT. The reaction was concentrated and CH2Cl2ZMeOH was added to dissolve the residue. Much of the solid did not dissolve so the mixture was filtered to give 2-Methanesulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one, as an off-white solid (2.31 g, 11.04 mmol, 43%). MS: APCI: M+l: 210.1 (Exact Mass: 209.03).

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 211244-81-4, 2-(Methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2006/90272; (2006); A1;,
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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. 271-70-5, name is 7H-Pyrrolo[2,3-d]pyrimidine, the common compound, a new synthetic route is introduced below. Product Details of 271-70-5

A mixture of ethyl 2-(6-bromo-2-(4-methoxybenzyl)-3-oxoisoindolin-1-yl)acetate (3, 439 mg, 1.05 mmol), 7H-pyrrolo[2,3-d]pyrimidine (4, 125 mg, 1.05 mmol), tris(dibenzylideneacetone)dipalladium(0) (97 mg, 0.10 mmol), XantPhos (61 mg, 0.10 mmol), and cesium carbonate (752 mg, 2.31 mmol) in 1,4-dioxane (25 mL) was purged with argon for 5 min. The reaction was stirred at 110 C. for 16 h. Upon cooling, the reaction mixture was diluted with ethyl acetate, washed with half saturated aqueous sodium bicarbonate solution, and then with brine. The organic layer was dried over magnesium sulfate, filtered and concentrated. The crude product was purified via column chromatography (silica, methanol/dichloromethane gradient from 0-5% to afford ethyl 2-(2-(4-methoxybenzyl)-3-oxo-6-(7H-pyrrolo[2,3-d]pyrimidin-7-yl)isoindolin-1-yl)acetate (5). Yield: 333 mg, 70%; MS (ESI) m/z 457.4[M+1]+.

The synthetic route of 271-70-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EFFECTOR THERAPEUTICS, INC.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; (55 pag.)US2017/121339; (2017); A1;,
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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. 63558-65-6, name is 4-Chloro-5-iodopyrimidine, the common compound, a new synthetic route is introduced below. Recommanded Product: 4-Chloro-5-iodopyrimidine

Step 3: N-4′-[(5-Iodopyrimidin-4-yl)amino]-6-methylbiphenyl-3-yl-3-(trifluoromethyl)benzamideTo lambda^-(4′-amino-6-methylbiphenyl-3-yl)-3-(trifluoromethyl)benzamide (60.0 mg, 0.162 mmol) was added 4-chloro-5-iodopyrimidine (39 mg, 0.16 mmol) followed by ethanol (0.47 mL). The reaction was heated to 80 0C in a sealed tube until LCMS indicated complete reaction, typically 1 -2 hours. The reaction was cooled to ambient temperature and the solvent was evaporated. The residue was partitioned between saturated aqueous NaHCO3 and EtOAc, the organic phase was washed with brine, dried (MgSO4) and evaporated to leave the crude product, which was then purified by column chromatography to give the final compound (39.9 mg, 42.88%). 1H NMR (400 MHz, CDCl3): delta 8.61 (s, 2H), 8.14 (s, IH), 8.08 (d, IH), 7.95 (s, IH), 7.81 (d, IH), 7.5-7.7 (m, 5H), 7.40 (m, 3H), 7.29 (d, IH), 2.29 (s, 3H). MS (EI) m/z = 575 (M+H).

The synthetic route of 63558-65-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INCYTE CORPORATION; WO2008/79965; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 4983-28-2, 2-Chloro-5-hydroxypyrimidine, 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, 4983-28-2, blongs to pyrimidines compound. Recommanded Product: 4983-28-2

To a solution of 2-((6-(tert-butylsulfonyl)-4-((4,5-dimethyl-lH-pyrazol-3-yl)amino)quinazolin-7- yl)oxy)ethanol (247 mg, 0.589 mmol) in THF (5 mL) was added 2-chloropyrimidin-5-ol (85 mg, 0.648 mmol), triphenylphosphine (232 mg, 0.883 mmol) and DIAD (0.172 mL, 0.883 mmol) and the reaction was stirred at 20 ¡ãC under an atmosphere of nitrogen for 42 hours. The reaction was concentrated, and the residue was subjected directly to purification by flash chromatography (60g pre-packed C-18 SNAP cartridge: 5percent to 30percent acetonitrile (0.1percent formic acid) in water (0.1percent formic acid)). The desired fractions were combined and concentrated to afford the title compound (167 mg, 0.31 mmol, 53.3 percent yield). LCMS RT= 0.73 min, ES+ve 532.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4983-28-2, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CASILLAS, Linda N.; HARLING, John David; MIAH, Afjal Hussain; SMITH, Ian Edward David; RACKHAM, Mark David; (204 pag.)WO2017/182418; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 90914-41-3, 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]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, Quality Control of 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine, blongs to pyrimidines compound. Quality Control of 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine

1-(1-benzyl-4-piperidinyl)-3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine (Intermediate C) 3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine (Intermediate B) (5.0 g, 21.42 mmol), 1-benzyl-4-piperidinol (8.2 g, 42.83 mmol) and triphenylphosphine (11.23 g, 42.83 mmol)were suspended in 250 ml of tetrahydrofuran. The reaction mixture was cooled in an ice-water bath and diethyl azodicarboxylate (6.8 ml, 42.83 mmol) was added dropwise. 10 minutes later, the reaction mixture was allowed to warm up to room temperature. After stirring for 2 hours, solvent was removed and the residue was taking into ethyl acetate. The organic layer was washed, dried and evaporated. The crude product was passed through Biotage flash column using dichloromethane/ethyl acetate (90:10) as the mobile phase to yield 10.56 g of 1-(1-benzyl-4-piperidinyl)-3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine. The product was 61% pure with a HPLC retention time of 12.46 min. (HPLC condition: 5 to 95% CH3CN in 0.1 N aqueous ammonium acetate over 20 min., the column size is 3.9*150 mm, 300 A).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,90914-41-3, 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Abbott Laboratories; US2002/156081; (2002); A1;,
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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. 33034-67-2, name is 2-Chloro-4-(trifluoromethyl)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 2-Chloro-4-(trifluoromethyl)pyrimidine

General procedure: To a solution of D47 (4.86 mmol) in DMF (8 mL), K2CO3 (8.68 mmol) and Ar1-X (where X is2-chloro or fluoro; 5.8 mmol) were added. The reaction mixture was heated at 80-130 ¡ãC until complete conversion of the starting material. The resulting mixture was poured into aqueous solution of NH4Cl and extracted with AcOEt. The organic layer was dried andconcentrated to obtain a crude mixture which was purified by silica gel chromatography (cyclohexane/ethyl acetate from 10/0 to 8/2) to give the title compound as single diasteroisomer.

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, 33034-67-2, 2-Chloro-4-(trifluoromethyl)pyrimidine.

Reference:
Patent; ROTTAPHARM SPA; STASI, Luigi Piero; ROVATI, Lucio; WO2013/139730; (2013); A1;,
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Reference of 6693-08-9, 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 6693-08-9, name is 2,4,6-Trichloro-5-fluoropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 3-amino-5-isoproxypyrazole (1.75 g, 12.41 mmol) in THF (20 ml) was added triethylamine (1.51 g, 14.89 mmol) and then slowly a solution of 2,4,6-trichloro-5- fluoropyrimidine (WO200549033, 2.50 g, 12.41 mmol) in THF (20 ml) at 0 0C. The resulting mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue was diluted with EtOAc. The solution was then washed with brine twice. The organic layer was obtained and evaporated to dryness. The dried residue was subject to silica gel chromatographic purification (by ISCO Combiflash with gradient EtOAc/hexanes) to afford EPO the desired product (1.40 g, yield 79%). LC-MS, 264 (M-41); 1H NMR (CDCl3) delta 8.70 (s, IH), 5.90 (s, IH), 4.50 (m, IH), 1.22 (d, 6H).

According to the analysis of related databases, 6693-08-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/123113; (2006); A2;,
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Reference of 35265-82-8, 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 35265-82-8, name is 2,4-Dichloro-6-methylthieno[3,2-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

At normal temperature a solution of bromine (1.44 mE, 27.6 mmol) in acetic acid (10 mE) was slowly added dropwise into a solution of 8-g (prepared according to the method ofpatent: W02007/023382A2)(1.984 g, 9.2mmol) and aluminum trichloride (2.46 g, 18.4 mmol) in acetic acid (30 mE). The mixture was heated to 80 C. to react for 6 irs afier the addition was completed. The reaction mixture was cooled, and then partitioned between ethyl acetate (80 mE) and water (80 mE). The organic layer was separated and washed with 5% sodium thiosulfate solution (2×80 mE). The aqueous phase was extracted with ethyl acetate (x2), the combined organic phase was washed sequentially with saturated sodium bicarbonate solution (200 mE) and saturatedbrine (400 mE), dried over anhydrous sodium sulfate, and concentrated under reduced pressure, to yield target compound 8-f(1 .035 g, yield 76%) as a pale yellow solid. EC-MS (ESI): mlz 296.9 (M+H).

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 35265-82-8, 2,4-Dichloro-6-methylthieno[3,2-d]pyrimidine.

Reference:
Patent; SHANGHAI YINGLI PHARMACEUTICAL CO., LTD; XU, Zusheng; (174 pag.)US2016/214994; (2016); A1;,
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Related Products of 65996-50-1, 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 65996-50-1 as follows.

(4) To 1,5-dihydro-pyrrolo[3,2-d]pyrimidine-2,4-dione (35.0g) was added aqueous 1N sodium hydroxide solution (231ml) and after stirring for a while, the mixture was concentrated in vacuo. The residue was subjected to azeotropic distillation with toluene. To the residue was gradually added phenylphosphonic dichloride (239g) and then the temperature of the mixture was raised to 180C, followed by stirring for 3 hours. Thereto was further gradually added phenylphosphoric dichloride (100g) and the mixture was stirred overnight. The reaction mixture was gradually poured into ice-water under stirring and the mixture was extracted with ethyl acetate. The organic layer was washed with aqueous sodium bicarbonate solution, dried and concentrated in vacuo. To the residue was added ethyl acetate/ diisopropyl ether to give 2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine as crystals (19.96g). APCI-MS (m/e): 188/190 (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,65996-50-1, its application will become more common.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; EP1956009; (2008); A1;,
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Pyrimidine – Wikipedia

Related Products of 1152107-25-9, Adding some certain compound to certain chemical reactions, such as: 1152107-25-9, name is Gsk-1322322,molecular formula is C22H34FN7O4, 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 1152107-25-9.

Example 10 Synthesis of N-(( ?)-2-(cyclopentylmethyl)-3-(2-(5-fluoro-6-((S)- hexahydro pyrazino[2,1 -c][1,4]oxazin-8(1 H)-yl)-2-methylpyrimidin-4- yl)hydrazinyl)-3-oxopropyl)-N-hydroxyformamide methanesulfonateN-(( ?)-2-(cyclopentylmethyl)-3-(2-(5-fluoro-6-((S)-hexahydropyrazino[2,1- c][1,4]oxazin-8(1 H)-yl)-2-methylpyrimidin-4-yl)hydrazinyl)-3-oxopropyl)-N- hydroxyformamide methanesulfonateTo a 1-L Labmax was added N-(( )-2-(cyclopentylmethyl)-3-(2-(5-fluoro-6-((S)- hexahydropyrazino[2, 1-c][1 ,4]oxazin-8(1 H)-yl)-2-methylpyrimidin-4-yl)hydrazinyl)-3- oxopropyl)-N-hydroxyformamide (100 g, 209 mmol) and n-Propanol (600 mL). The contents were heated to 60C and methanesulfonic acid (13.54 mL, 209 mmol) was added via pipette. Solution was transferred through filter paper and into a clean 1-L Labmax. A rinse of n-propanol (100 mL) was transferred through the filter and into the clean 1-L Labmax. The resulting solution was adjusted to 50C. The solution was seeded with N-((f?)-2-(cyclopentylmethyl)-3-(2-(5-fluoro-6-((S)-hexahydropyrazino[2, 1- c][1 ,4]oxazin-8(1 H)-yl)-2-methylpyrimidin-4-yl)hydrazinyl)-3-oxopropyl)-N- hydroxyformamide methanesulfonate Form 1 (1.0 g, 1.7 mmol). The resulting slurry was aged for 1 hour at 50C. The slurry was cooled to 20C at a linear rate of0.1 C/min. The slurry was aged for 2 hours at 20C. The slurry was cooled to 0C at a linear rate of 0.1 C/min and aged overnight. The slurry was filtered under nitrogen and the cake was washed with chilled n-propanol (100 mL). The resulting wet cake was blown with nitrogen. The wet cake was then dried under vacuum at 50C. After drying, 104 g (86.7% yield) of N-(( )-2-(cyclopentylmethyl)-3-(2-(5-fluoro-6-((S)- hexahydropyrazino[2, 1-c][1 ,4]oxazin-8(1 H)-yl)-2-methylpyrimidin-4-yl)hydrazinyl)-3- oxopropyl)-N-hydroxyformamide methanesulfonate was obtained. H NMR (500 MHz, DMSO-d6, referenced to TMS = 0.00 ppm, T = 25 C, rotamers present due to hindered rotation, major rotamers listed with integration rounded to nearest 1/2 units) delta ppm 10.5-9.7 (3H, several broad s), 9.05 (1/2 H, s), 9.02 (1/2 H, s), 8.31 (1/2 H, s), 7.87 (1/2 H, s), 4.38 (1 H, d, J = 13 Hz), 4.30 (1 H, d, J = 14 Hz), 4.08-4.00 (2H, several m), 3.80-3.72 (3/2 H, several m), 3.56-3.24 (17/2 H, several m), 3.02-2.98 (1 H, m), 2.82-2.69 (1 H, several m), 2.38 (3H, s), 2.26-2.23 (3H, several s), 1.99-1.90 (2H, several m), 1.71 (1 H, broad m), 1.66-1.47, (5H, several m), 1.27- 1.20 (1 H, m), 1.08-1.02 (2H, several m).3C NMR (126 MHz, DMSO-d6, referenced to DMSO-d6 = 39.51 ppm, T = 25 C, rotamers present due to hindered rotation, major rotamers listed with integration rounded to nearest 1/2 units) delta ppm 172.8 (rotamer 1/2 C), 172.7 (rotamer 1/2 C), 162.0 (rotamer 1/2 C), 160.1 (d, J13C-I9F = 9 Hz) (rotamer 1/2 C), 160.0 (d, J13C-I9F = 9 Hz) (rotamer 1/2 C), 157.4 (rotamer 1/2 C), 152.5 (d, J13C-I9F = 10 Hz), 148.2 (broad), 130.4 (d, J13C-19F = 249 Hz) (rotamer 1/2 C), 130.3 (d, J13C-I9F = 249 Hz) (rotamer 1/2 C), 65.2, 63.7, 60.1 , 52.0 (rotamer 1/2 C), 51.7, 51.4, 48.9 (rotamer 1/2 C), 43.8 (broad), 43.4 (broad), 41.2 (rotamer 1/2 C), 41.1 (rotamer 1/2 C), 39.8, 37.0 (rotamer 1/2 C), 36.9 (rotamer 1/2 C), 35.6 (rotamer 1/2 C), 35.5 (rotamer 1/2 C), 32.9, 31.6, 24.9, 24.7 (2C).HRMS (ESI): calcd for C22H35FN704[M + H]+ 480.2730, found 480.2731.

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. 1152107-25-9, Gsk-1322322, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY NO 2 LIMITED; BULLOCK, Kae Miyake; DESCHAMPS, Nicole; ELITZIN, Vassil; FITZGERALD, Russell; GRADDY, William Hawthorne; MATSUOKA, Richard Tadao; MCKEOWN, Robert Rahn; MITCHELL, Mark Bryan; SHARP, Matthew Jude; SUTTON, Peter W.; TABET, Elie Amine; ZHOU, Xiaoming; WO2014/141181; (2014); A1;,
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