Pyrimidines

Reference of 13566-63-7, Adding some certain compound to certain chemical reactions, such as: 13566-63-7, name is 4,6-Dimethoxy-5-methylpyrimidine,molecular formula is C7H10N2O2, 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 13566-63-7.

Example 3Preparation of 1-(4,6-dimethyl-2-pyridinyl)ethanone O-[(4,6-dimethoxy-5-pyrimidinyl)methyl]oxime (Compound No. II-17) [43.1] 0.50 g (3.05 mmol) of 4,6-dimethoxy-5-methylpyridine was dissolved in 15 ml of carbon tetrachloride, and 0.58 g (3.26 mmol) of N-bromosuccinimide was added. The resulting solution was irradiated with light (infrared light 375 WR, produced by Toshiba Co., Ltd.) for 2 hours at the refluxing temperature. The reaction solution was cooled to room temperature. The deposited succinimide was separated by filtration. The filtrate was concentrated under reduced pressure to give a crude product of 5-bromomethyl-4,6-dimethoxypyridine. Meanwhile, to a solution of 0.43 g (2.62 mmol) of 1-(4,6-dimethyl-2-pyridinyl)ethanone oxime in 10 ml of N,N-dimethylformamide was added 0.13 g (3.25 mmol) of sodium hydride (oiliness: 60%) while cooling in an ice bath, and the solution was stirred at the ice temperature for 30 minutes. To the resulting solution was added the whole amount of the previously prepared crude product of 5-bromomethyl-4,6-dimethoxypyridine while cooling in an ice bath, and the solution was stirred at room temperature for an hour. The reaction solution was poured into ice-water, and extracted with diethyl ether. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography [eluted with n-hexane:ethyl acetate = 7:3 (v/v)] to give 0.44 g of the target compound. Melting point: 125 to 126C.; Example 6Preparation of 4-cyano-6-methyl-2-pyridinecarboxyaldehyde O-[(4,6-dimethoxy-5-pyrimidinyl)methyl]oxime (Compound No. II-29) [51.1] To a solution of 1.0 g (6.49 mmol) of 4,6-dimethoxy-5-methylpyrimidine in 10 ml of carbon tetrachloride was added 1.27 g (7.13 mmol) of N-bromosuccinimide. . The resulting solution was irradiated with light (infrared light 375 WR, produced by Toshiba Co., Ltd.) for an hour at the refluxing temperature. The reaction solution was cooled to room temperature. The deposited succinimide was separated by filtration. The filtrate was concentrated under reduced pressure to give a crude product of 5-bromomethyl-4,6-dimethoxypyrimidine. Meanwhile, to a solution of 1.06 g (6.50 mmol) of N-hydroxyphthalimide in 10 ml of N,N-dimethylformamide was added 0.72 g (7.13 mmol) of triethylamine. The resulting solution was heated to 70C, and the whole amount of the previously prepared crude product of 5-bromomethyl-4,6-dimethoxypyrimidine was added therein, followed by stirring at 70C for 2 hours. The reaction solution was cooled to room temperature, poured into ice-water, and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 1.46 g of a crude product of N-[(4,6-dimethoxy-5-pyrimidinyl)methyloxy]phthalimide. The whole amount of the obtained crude product of N-[(4,6-dimethoxy-5-pyrimidinyl)methyloxy]phthalimide was dissolved in 10 ml of methanol, and 0.28 g (5.60 mmol) of hydrazine monohydrate was added therein, followed by stirring at room temperature for an hour. The reaction solution was concentrated under reduced pressure, and dissolved in ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 0.67 g of a crude product of (4,6-dimethoxy-5-pyrimidinyl)methyloxyamine. 0.67 g (4.59 mmol) of 4-cyano-6-methyl-2-pyridinecarboxyaldehyde was dissolved in 10 ml of glacial acetic acid. To the resulting solution were added, at room temperature, 0.37 g (4.51 mmol) of sodium acetate and then the whole amount of the previously prepared (4,6-dimethoxy-5-pyrimidinyl)methyloxyamine, and the solution was stirred further at room temperature for 2 hours. The reaction solution was poured into ice-water, and extracted with ethyl acetate. The ethyl-acetate layer was neutralized with a 5% aqueous solution of sodium hydrogen carbonate, washed with saturated salt water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography [eluted with benzene:ethyl acetate = 9:1 (v/v)] to give 0.43 g of the target compound. Melting point: 160 to 161C.; ii) Preparation of 2-(4,6-dimethyl-2-pyridinyl)-2-[(2,4-dimethoxy-3-pyridinyl)methyloxyimino]acetonitrile [72.1] 0.30 g (1.94 mmol) of 4,6-dimethoxy-5-methylpyrimidine was dissolved in 4 ml of carbon tetrachloride, and 0.38 g (2.13 mmol) of N-bromosuccinimide was added therein. The resulting solution was irradiated with light (infrared light 375 WR, produced by Toshiba Co., Ltd.) for 2 hours at the refluxing temperature. The solution was cooled to room temperature. The deposited succinimide was separated by filtration. The filtrate was concentrated under reduced pressure to give a crude product of 5-bromomethyl-4,6-dimethoxypyrimidine. Meanwhile, …

According to the analysis of related databases, 13566-63-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NIPPON SODA CO., LTD.; EP1362850; (2003); A1;,
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Reference of 945950-37-8, 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. 945950-37-8, name is 4-Methyl-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below.

a- Synhtesis of Int. 402: A sol. of 4-methyl-7H-pyrrazolo[2,3-d]pyrimidine (3.11 g, 23.4 mmol) in DMF (40 mL) was cooled to 0C and treated with NaH 60% (1.40 g, 35.0 mmol). The r.m. was stirred at 0C for 2h then 2-(trimethylsilyl)ethoxymethyl chloride (4.96 mL, 28.0 mmol) was added. The r.m. was stirred at r.t. for 2h and diluted in EtOAc. The organic layer was washed with water and brine (twice), dried over MgS04 and evaporated in vacuo to give brown oil. The oil was purified by prep. LC (irregular SiOH 15-40 muiotaeta, 80g, Grace, mobile phase gradient: from DCM 100% to DCM 96%, MeOH 4%). The desired fractions were collected and solvent evaporated until dryness to give 3.53 g. The residue was purified by prep. LC (irregular SiOH 15-40 muiotaeta, 80g, Grace, mobile phase gradient: from DCM 100% to DCM 96%, MeOH 4%). The pure fractions were collected and solvent evaporated until dryness to give 1.56 g of Int. 402 as a brown oil (25%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,945950-37-8, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; MEVELLEC, Laurence, Anne; PASQUIER, Elisabeth, Therese, Jeanne; DESCAMPS, Sophie; MERCEY, Guillaume, Jean, Maurice; WROBLOWSKI, Berthold; VIALARD, Jorge, Eduardo; MEERPOEL, Lieven; JEANTY, Matthieu, Ludovic; JOUSSEAUME, Thierry, Francois, Alain, Jean; WO2015/144799; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 50270-27-4, 2,4,6-Trichloropyrimidine-5-carbaldehyde, 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, 50270-27-4, blongs to pyrimidines compound. category: pyrimidines

To a solution of 2,4,6-trichloropyrimidine-5-carbaldehyde (3.50 g, 16.6 mmol) in THF (50 mL)was added N2H4.H20 (830 mg, 16.6 mmol) slowly at-lO °C. Then, Et3N (2.51 g, 24.9 mmol)was added to the mixture at -10 00. The mixture was stirred at -10 °C for 30 mm. The mixture was concentrated. The residue was purified by column chromatography (petroleum ether: ethyl acetate = 10: 1) to give the title compound (1.25 g, yield 40percent) as a yellow solid. 1H NMR (300 MHz, CDCI3): 611.61 (brs, 1H), 8.25 (s, IH).LCMS [mobile phase: 5-95percent CH3CNJ: Rt = 2.005 mm;MS Calcd: 188; MS Found: 189 [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,50270-27-4, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R & D COMPANY LIMITED; DING, Xiao; JIN, Yun; LIU, Qian; REN, Feng; SANG, Yingxia; STASI, Luigi Piero; WAN, Zehong; WANG, Hailong; XING, Weiqiang; ZHAN, Yang; ZHAO, Baowei; (573 pag.)WO2017/12576; (2017); A1;,
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Reference of 769-42-6, 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 769-42-6 as follows.

General procedure: To a mixture of aldehyde (1.1 mmol), beta-naphthol(1.0 mmol), and 1,3-dimethylbarbutyric acid (1.0 mmol),3 mol% of ZrOCl2/nano-TiO2 were added as the catalyst,and the mixture was stirred for an appropriate time at 100C in an oil bath. After completion of the reaction, indicatedby TLC, the reaction mixture was dissolved in the appropriatevolume of hot ethanol, stirred for 5 min, filtered,and the heterogeneous catalyst recovered. Solution withproduct was concentrated and recrystallized from ethanolto get pure compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,769-42-6, its application will become more common.

Reference:
Article; Mohaqeq, Mahboubeh; Safaei-Ghomi, Javad; Shahbazi-Alavi, Hossein; Acta Chimica Slovenica; vol. 62; 4; (2015); p. 967 – 972;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 2240-25-7, 4-Amino-5-bromopyrimidin-2(1H)-one, 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, 2240-25-7, blongs to pyrimidines compound. Application In Synthesis of 4-Amino-5-bromopyrimidin-2(1H)-one

A mixture of compound 5-bromocytosine (150 g, 789 mmol, 1.00 equiv) and ethyl 3- bromo-2-oxo-propanoate (385 g, 1.97 mol, 247 mL, 2.50 equiv) in AcOH (1.5 L) was stirred at 120 C for 2 h. The crude 1H NMR spectrum indicated that the reaction was complete. Three batches were concentrated to provide a residue that was triturated with MTBE (3 L) and filtered. The filter cake was washed with water (1 L x 4) and dried to afford ethyl 8-bromo-5-oxo-5, 6- dihydroimidazo[l, 2-c]pyrimidine-2-carboxylate (300 g, 1.05 mol, 44.3% yield) as a brown solid. 1H NMR (400MHz, DMSO-d6) d 12.47 – 11.64 (m, 1H), 8.33 (s, 1H), 8.06 (s, 2H), 7.73 (s, 1H), 4.31 (q, 7= 7.1 Hz, 2H), 1.32 (t, J= 7.1 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2240-25-7, its application will become more common.

Reference:
Patent; MIRATI THERAPEUTICS, INC; MARX, Matthew, Arnold; LEE, Matthew, Randolph; BOBINSKI, Thomas, P.; BURNS, Aaron, Craig; ARORA, Nidhi; CHRISTENSEN, James, Gail; KETCHAM, John, Nichael; (225 pag.)WO2019/152419; (2019); A1;,
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Synthetic Route of 5305-59-9, 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.5305-59-9, name is 6-Chloropyrimidin-4-amine, molecular formula is C4H4ClN3, molecular weight is 129.55, as common compound, the synthetic route is as follows.

EXAMPLE 22 A mixture of 8.0 g (0.062 mole) of 4-amino-6-chloropyrimidine and 10.8 g (0.124 mole) of morpholine in 100 ml of toluene was heated at its reflux temperature for 20 hours, and was then cooled. The solid was separated by filtration, washed with toluene, and slurried in 100 ml of water followed by filtration. Recrystallization from water provided yellow crystals of 4-amino-6-(4-morpholino)pyrimidine, m.p. 198-201 C. Analysis: Calculated for C8 H12 N4 O: %C,53.3; %H,6.7; %N,31.1; Found: %C,53.5; %H,6.5; %N,31.3.

Statistics shows that 5305-59-9 is playing an increasingly important role. we look forward to future research findings about 6-Chloropyrimidin-4-amine.

Reference:
Patent; Riker Laboratories, Inc.; US4503050; (1985); A;,
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Pyrimidine – Wikipedia

Electric Literature of 56-09-7, 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. 56-09-7, name is 2-Amino-6-hydroxypyrimidin-4(3H)-one. A new synthetic method of this compound is introduced below.

1. Formation of Compound for formula 5 :; Initially, a compound of formula 6 was reacted with POC13 in DMF and heat to form a compound of formula 5. NH2 aH2 JE JE N-N N-N HO4OH X) 9AX formula 6 o formula 5 The compound of formula 5 subsequently treated, (details below) to practice the process of the claimed invention. As seen below, a compound of formula 5, wherein X is chloride, is subsequently reacted to form an intermediate compound of formula 11.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,56-09-7, 2-Amino-6-hydroxypyrimidin-4(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; SCHERING CORPORATION; WO2005/54245; (2005); A2;,
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Pyrimidine – Wikipedia

Related Products of 696-82-2, 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. 696-82-2, name is 2,4,6-Trifluoropyrimidine. A new synthetic method of this compound is introduced below.

(S)-1-(1-(4-Fluorophenyl)-1H-pyrazol-4-yl)ethanamine (175 mg, 0.724 mmol) was added to a solution of 2,4,6-trifluoropyrimidine (146 mg, 1.09 mmol, 1.5 equiv) and N-ethyl-N-isopropylpropan-2-amine (0.32 mL, 1.8 mmol, 2.5 equiv) in 1,4-dioxane at room temperature. The mixture was stirred at room temperature for 1 hour and then the reaction was concentrated in vacuo. Silica gel column chromatography (EtOAc/Heptane) provided (R)-4- ((R)- 1 -(tert-butoxy)ethyl)-3-(2-chloro-6-(hydroxymethyl) pyri midin-4-yl)oxazolidin-2-one (0.085 g) in 37% yield. 1H NMR (400 MHz, ODd3) oe 7.82 (5, 1H), 7.68 (5, 1H), 7.62 (dd, J = 8.9, 4.6 Hz,1H), 7.18-7.11, (m, 2H), 5.80 (t, J = 1.2 Hz, 1H), 5.49 (m, 1H), 5.25 (m, 1H), 1.62 (d, J = 6.8 Hz, 3H). MS m/z 320.1 (M + H) Rt-0.95 mm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,696-82-2, its application will become more common.

Reference:
Patent; NOVARTIS AG; CAFERRO, Thomas Raymond; CHEN, Zhuoliang; CHO, Young Shin; COSTALES, Abran Q.; LEVELL, Julian Roy; LIU, Gang; MANNING, James R.; SENDZIK, Martin; SHAFER, Cynthia; SHULTZ, Michael David; SUTTON, James; WANG, Yaping; ZHAO, Qian; WO2014/141104; (2014); A1;,
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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.7043-09-6, name is 4,6-Dichloro-2-cyclopropylpyrimidine, molecular formula is C7H6Cl2N2, molecular weight is 189.04, as common compound, the synthetic route is as follows.category: pyrimidines

To a suspension of Nal (2.10 g, 13.7 mmol) in HI (55%, 10 mL) was added 4,6-dichloro-2- cyclopropylpyrimidine (2.00 g, 10.6 mmol). The resulting mixture was warmed to 40 C and stirred for 1 hour. The reaction mixture was cooled to rt and diluted with H20 (100 mL) and stirred for 15 mm. The mixture was filtered to give the title compound (2.9 g, yield 74%) as ayellow solid.1H NMR (300 MHz, CDCI3): oe 7.95 (s, 1H), 2.21-2.12 (m, 1H), 1.15-1.09 (m, 4H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7043-09-6, 4,6-Dichloro-2-cyclopropylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R & D COMPANY LIMITED; DING, Xiao; JIN, Yun; LIU, Qian; REN, Feng; SANG, Yingxia; STASI, Luigi Piero; WAN, Zehong; WANG, Hailong; XING, Weiqiang; ZHAN, Yang; ZHAO, Baowei; (573 pag.)WO2017/12576; (2017); A1;,
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Pyrimidine – Wikipedia

Related Products of 941685-26-3, Adding some certain compound to certain chemical reactions, such as: 941685-26-3, name is 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine,molecular formula is C12H18ClN3OSi, 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 941685-26-3.

A mixture of Intermediate 5 (60 g, 330.5 mmol), 2-[(4-chloropyrrolo[2,3-d]pyrimidin-7- yl)methoxy]ethyl-trimethyl-silane (85 g, 330.5 mmol) and DIPEA (108 mL, 625 mmol) in dry MeCN (500 mL) was refluxed for 16 hours. All the volatiles were evaporated and the resulting residue was treated with water and extracted with ethyl acetate (2 x 500 mL). The combined organic layers were washed with brine (500 mL), dried over Na2S04, concentrated and chromatographed on silica using EtOAc: heptane as eluent. Ethyl 5-[7-(2- trimethylsilylethoxymethyl)pyrrolo[2,3-d]pyrimidin-4-yl]-5-azaspiro[2.5]octane-8- carboxylate (rac-SEM ethyl ester) was isolated as a light brown oil (63 g) in 49% yield and used directly in the next step.

According to the analysis of related databases, 941685-26-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LEO PHARMA A/S; LARSEN, Mogens; RITZEN, Andreas; NØRREMARK, Bjarne; GREVE, Daniel Rodriguez; (145 pag.)WO2018/141842; (2018); A1;,
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