Pyrimidines

Related Products of 347418-42-2, 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 347418-42-2 as follows.

Step 2 17.5 g Sodium hydride (60% dispersion in mineral oil) was suspended in300 ml N,N-dimethylformamide. The reaction mixture was cooled with an ice- water bath. 70.0 ml Diethyl malonate was added dropwise over 45 minutes. The resulting clear mixture was stirred at ambient temperature for 30 minutes. 36.2 g Crude product from the preceded step was added dropwise over 20 minutes at ambient temperature. The orange reaction mixture was stirred at ambient temperature. Reaction progress was monitored with HPLC. After 18 hours, the reaction mixture was concentrated in vacuo to remove most of the N,N- dimethylformamide.300 ml diethyl ether and100 ml water were added and the mixture was stirred vigorously for 5 minutes. The pH of the mixture was adjusted to ~7 with aqueous hydrochloric acid (1.5 M). The layers were separated and150 ml diethyl ether was added to the aqueous layer. The pH was again adjusted to ~7. The combined organic layers were washed with300 ml brine, dried (Na2S04) and concentrated in vacuo. The obtained yellow oily liquid contained still some mineral oil (floating on top). Most of the mineral oil was removed by using a separation funnel. The excess of diethyl malonate still present was removed by vacuum distillation (80C, 0.65 mbar). The product diethyl (5- fluoro-4-pyrimidinyl)malonate was isolated as a yellow oily liquid (89.6% purity acc. HPLC, NMR confirms expected structure) that was used directly in the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,347418-42-2, its application will become more common.

Reference:
Patent; SYNTHRON B.V.; OVEREEM, Arjanne; ZHU, Jie; WO2011/110198; (2011); A1;,
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Synthetic Route of 504-17-6 ,Some common heterocyclic compound, 504-17-6, 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: A mixture of an aldehyde (0.25mmol), 2-thiobarbituric acid (0.5mmol), ammonium acetate (0.3mmol) and CuFe2O4 (10mol%) were added in distilled H2O. Then, ultrasonic probe was directly immersed in the resulting mixture. After completion of the reaction (TLC), the solvent was evaporated and the precipitate was washed from ethanol and hot water to afford the pure product. All products were identified by physical and spectroscopic data.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,504-17-6, its application will become more common.

Reference:
Article; Naeimi, Hossein; Didar, Asieh; Ultrasonics Sonochemistry; vol. 34; (2017); p. 889 – 895;,
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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.130049-82-0, name is 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one, molecular formula is C11H15ClN2O2, molecular weight is 242.7, as common compound, the synthetic route is as follows.HPLC of Formula: C11H15ClN2O2

300 ml of acetonitrile was charged followed by 20.0 g of 3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido-[1,2-a]-pyrimidin-4-one and 21.0 g of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole hydrochloride at room temperature. The reaction mass was stirred at room temperature for 5 minutes and 20.0 g of potassium carbonate and 0.7 g of potassium iodide were charged. Further, 0.2 g of sodium borohydride was charged and the temperature was raised to 65±2 C. The reaction mass was maintained at 65±2 C. for 25 hours. After reaction completion, the reaction mass was slowly cooled to room temperature. The solids were filtered, washed with 50 ml of acetonitrile and then dissolved in 800 ml of methylene chloride at room temperature. The contents were heated to 30-35 C., maintained for 10 minutes, filtered and washed with 20 ml of methylene chloride. The clear filtrate was distilled completely under vacuum below 35 C. and replaced with 50 ml of acetone. Further, 300 ml of acetone was charged, heated to 45 C. and stirred for 30 minutes. The reaction mass was cooled to room temperature and stirred for 1 hour. The product was filtered, washed with 20 ml of acetone and dried under vacuum at 50-55 C. to yield paliperidone (30 g, yield: 150% w/w, efficiency: 85.11%, keto impurity by HPLC: 0.01%, total impurity level by HPLC: 1.0%)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,130049-82-0, 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one, and friends who are interested can also refer to it.

Reference:
Patent; CIPLA LIMITED; Puppala, Ravikumar; Pathi, Srinivas Laxminarayan; Kankan, Rajendra Narayanrao; US2014/200228; (2014); 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. 4595-60-2, name is 2-Bromopyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2-Bromopyrimidine

General procedure: A Schlenk tube was charged with the prescribed amount of catalyst, aryl halide (1.0 mmol), 3-(hydroxymethyl)phenylboronicacid (1.5 mmol), TBAB (1.0 mmol), the selected base (3.0 mmol), and water under nitrogen atmosphere. The reaction mixture was heated at 100 C for 12 h. After cooling,the mixture was extracted with CH2Cl2, the solvent was evaporated,and the product was separated by passing through a silica gel column with CH2Cl2/ethyl acetate (5:1) aseluent. The products 2f, 2j, 2l, and 2o were new compounds and were determined by 1H and C13 NMR. Other products were characterized by comparison with data in the literature.

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, 4595-60-2, 2-Bromopyrimidine.

Reference:
Article; Gao, Hui; Xu, Chen; Li, Hong-Mei; Lou, Xin-Hua; Wang, Zhi-Qiang; Fu, Wei-Jun; Bulletin of the Korean Chemical Society; vol. 36; 9; (2015); p. 2355 – 2358;,
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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. 213265-83-9, name is 4,6-Dichloro-5-fluoropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. name: 4,6-Dichloro-5-fluoropyrimidine

Example 1.1: Preparation of 4-(l-(5-Ethylpyrimidin-2-yl)piperidin-4-yloxy)-5-fluoro-6-(2- methyl-6-(methylsulfonyl)pyridin-3-yloxy)pyrimidine (Compound 1).Step A: Preparation of tert-Butyl 4-(6-Chloro-5-fluoropyrimidin-4- yloxy)piperidine-l-carboxylate.To a solution of 4,6-dichloro-5-fluoropyrimidine (1.00 g, 5.99 mmol) and teri-butyl 4- hydroxypiperidine-1 -carboxylate (1.205 g, 5.99 mmol) in THF (10 mL) at -78 C was added 1 M potassium teri-butoxide solution in THF (5.99 mL, 5.99 mmol) dropwise. The mixture became thick and additional THF (10 mL) was slowly added. After stirring for 15 min, the mixture was diluted with water and extracted with EtOAc. The organic layer was concentrated under reduced pressure and purified by silica gel flash column chromatography to give the title compound as a colorless oil that slowly became a white solid (1.9561 g, 98%). Exact mass calculated for ^Eta19alphaRhoNu303: 331.1, found: LCMS m/z = 332.4 [M+H]+; lU NMR (400 MHz, CDC13) delta ppm 1.45 (s, 9H), 1.75-1.85 (m, 2H), 1.98-2.04 (m, 2H), 3.28-3.36 (m, 2H), 3.75-3.81 (m, 2H), 5.30-5.39 (m, 1H), 8.31 (s, 1H).

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, 213265-83-9, 4,6-Dichloro-5-fluoropyrimidine.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; WO2012/145604; (2012); A1;,
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Application of 4359-87-9 ,Some common heterocyclic compound, 4359-87-9, molecular formula is C4Cl3N3O2, 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.

2,4,6-Trichloro-5-nitropyrimidine (45, 1.43 g, 6.26 mmoles) was dissolved in dichloromethane and cooled to 0 C. A solution of 8-oxa-3-azabicyclo[3.2.1]octane (2, 0.934 g, 6.26 mmoles) in dichloromethane and triethylamine (0.873 ml_, 6.26 mmoles) was slowly added over 1 hour. The solution was allowed to stir at 0 C for 2 hours, then warmed to room temperature and stirred for an additional 16 hours. The reaction mixture was filtered, the filtrate was concentrated, dissolved in ethyl acetate, washed with 1 N hydrochloric acid, saturated sodium bicarbonate, brine, dried, and concentrated to provide 3-(2,6-dichloro-5-nitropyrimidin-4- yl)-8-oxa-3-azabicyclo[3.2.1]octane (46). Yield: 1.53 g (80%). HRMS; [M+H]+ Obs’d = 305.0200, [M+H]+ Calc’d = 305.0203.

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. 4359-87-9, 2,4,6-Trichloro-5-nitropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WYETH LLC; VERHEIJEN, Jeroen, Cunera; ZASK, Arie; RICHARD, David, James; KAPLAN, Joshua, Aaron; CURRAN, Kevin, Joseph; WO2010/120998; (2010); A1;,
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Related Products of 304693-66-1, 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.304693-66-1, name is 2-(Trifluoromethyl)pyrimidine-5-carbaldehyde, molecular formula is C6H3F3N2O, molecular weight is 176.096, as common compound, the synthetic route is as follows.

To a magnetically stirred solution of methyl Grignard (19.9 mL of a 3 M solution in ether (Et2O), 59.7 mmol) in Et2O (167 mL) was added a solution of 2-trifluoromethylpyrimidine-5-carbaldehyde (9.56 g, 54.3 mmol) in Et2O (50 mL) at 0 C., and the resulting pale yellow solution was warmed to room temperature (RT) and stirred for 2.5 h. The reaction was quenched by the addition of saturated aqueous ammonium chloride (NH4Cl) (50 mL) at 0 C., and the mixture was warmed to RT. The phases were separated and the organic phase was dried over Na2SO4, filtered, and concentrated to give a light yellow oil (9.32 g crude). The oil was purified by flash chromatography (330 g SiO2, 0>100% EtOAc/hexanes gradient) to give 1-(2-trifluoromethylpyrimidin-5-yl)ethanol (E) (8.87 g, 85%) as a light yellow solid: mp 43-45 C.; 1H NMR (300 MHz, CDCl3) ? 8.92 (s, 2H), 5.15-5.07 (m, 1H), 2.26 (d, J=4.0 Hz, 1H), 1.62 (d, J=6.5 Hz, 3H); MS (EI) m/z 192 (M)+.

Statistics shows that 304693-66-1 is playing an increasingly important role. we look forward to future research findings about 2-(Trifluoromethyl)pyrimidine-5-carbaldehyde.

Reference:
Patent; DOW AGROSCIENCES LLC; US2010/56534; (2010); 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. 425394-89-4, name is 4,6-Dichloropyrimidin-5-ol, the common compound, a new synthetic route is introduced below. HPLC of Formula: C4H2Cl2N2O

(1) 5-(Benzyloxy)-4,6-dichloropyrimidine, INT 45 To a solution of INT 37 (content 90%, 6.50 g, 35.50 mmol) in DMF (120 mL) was added benzyl bromide (8.42 mL, 70.90 mmol) followed by potassium carbonate (14.70 g, 106.36 mmol). The reaction mixture was stirred at 60 C. for 1 hr. The mixture was concentrated. The residue was partitioned between EtOAc and water. The organic layer was washed with water and brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography (silica; cyclohexane/EtOAc gradient, 0-10%) to afford INT 45 as a colorless oil. UPLC-MS: MS (ESI): [M+H]+ 255.1, rt=1.15 min. 1H NMR (DMSO-d6): delta (ppm) 8.72 (s, 1H), 7.57-7.50 (m, 2H), 7.48-7.37 (m, 3H), 5.19 (s, 2H).

The synthetic route of 425394-89-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; ANGST, Daniela; GESSIER, Francois; VULPETTI, Anna; US2015/152068; (2015); A1;,
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Application of 151266-23-8, 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 151266-23-8 as follows.

Example 13. l-(4-(4-amino-l-cyclopentyl-lH-pyrazolo[3,4-d]pyrimidin-3-yl)phenyl)-3- (3-(trifluoromethyl)phenyl)urea (AD60); [0182] A synthetic strategy for Cmpd AD60 is depicted in Scheme 8 following. Scheme 8[0183] Reagent 3-iodo-lH-pyrazolo[3,4-d]pyrimidin-4-amine) (0.5g; 1.9 mmol; Apsel et al., 2008, Id.) was combined with cyclopentyl iodide (0.24 mL; 2.1 mmol), l .Og K2CO3, in 20 mL DMF and heated to 45 C under argon for 2 hours. The reaction was filtered to remove solid K2CO3, and the filtrate was combined with brine and the organic product was extracted in CH2Cl2 (3x 50 mL). The combined organic layer was concentrated in vacuo and purified by silica gel chromatography (MeOH/Chloroform; 5:95) to afford l-cyclopentyl-3- iodo-lH-pyrazolo[3,4-d]pyrimidin-4-amine (ESI-MS m/z [M+H]+ found 330.0, calculated 330.0). 4-nitrophenyl boronic acid (190 mg, 1.1 mmol; Sigma-Aldrich), was coupled to 1- cyclopentyl-3-iodo-lH-pyrazolo[3,4-d]pyrimidin-4-amine (150mg, 0.456 mmol) via the Suzuki reaction in 6 mL 1,2 methoxy ethane, 1 mL of saturated sodium carbonate, 1.65 mL EtOH, and 200 mg of polymer-bound tetrakis palladium. The reaction was stirred under argon for 12 hours at room temperature, filtered through Whatman paper to remove palladium, mixed with brine, extracted in chloroform and the product was subsequently purified on silica in EtOAc and concentrated in vacuo. The purified solid l~cyclopentyl-3-(4- nitrophenyl)-lH-pyrazolo[3,4-d]pyrimidin-4-amine (ESI-MS m/z [M+H]+ found 325.0, calculated 325.1 ; lOOmg, 0.31 mmol) was combined with Zinc dust (605 mg, 9.25 mmol), 10 mL THF, 0.35 mL HOAc for 12 hours at room temperature under Argon. The reaction was filtered through CeIi te, extracted with EtOAc and concentrated in vacuo to yield 3-(4- aminophenyl)-l -cyclopentyl- lH-pyrazolo [3, 4-d]pyrimidin-4-amine (ESI-MS m/z [M+H]+ found 295.0, calculated 295.2). To this reduced product, molar equivalents of3-(trifluoromethyl)phenyl isocyanate (Sigma-Aldrich) were added dropwise in ice-cold CH2C12. The reaction proceeded until completion as judged by TLC, was concentrated in vacuo, resuspended in 50:50 H20-CH3CN, and purified on a Cl 8 column in CH3CN/H20/0.1%TFA (1-100% gradient) to yield AD60 l-(4-(4-amino-l -cyclopentyl- IH- pyrazolo[3,4-d]pyrimidin-3-yl)phenyl)-3-(3-(trifluoromethyl)phenyl)urea (ESI-MS m/z [M+H]+ found 482.2, calculated 482.0).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,151266-23-8, its application will become more common.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; DAR, Arvin; SHOKAT, Kevan M.; WO2010/45542; (2010); A2;,
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Synthetic Route of 33097-11-9, 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. 33097-11-9, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbaldehyde, molecular formula is C6H4Cl2N2OS, 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 4; 4-Chloro-2-methylsulfinyl-8-(“4-trifluoromethyl-phenvD-8H- pyridor23-Patent; GLAXO GROUP LIMITED; WO2006/104917; (2006); A2;,
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