Pyrimidines

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. 16019-33-3, name is 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde, the common compound, a new synthetic route is introduced below. name: 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde

Step 1 : lambda/-[2-(4,6-Dichloro-5-pyrimidinyl)ethyl]-5-fluoro-2-pyridinamine (187)A round bottom flask was charged with 2-amino-5-fluoropyridine (0.323 g, 2.88 mmol) and cooled to -15C. Trifluoroacetic acid (2.5 ml_, 32.2 mmol) was added and the solution was stirred for 10 minutes at -15C. Na(OAc)3BH (0.89 g, 4.2 mmol) was added to the reaction mixture and stirred for 10 minutes. A solution of 209 (0.5 g, 2.62 mmol) in CH2CI2 (2.0 ml.) was added dropwise and the reaction mixture was stirred at -15C for 30 minutes, then stirred at RT for 15 h. Mixture was concentrated under reduced pressure, diluted with 10% NaHCO3, extracted with CH2CI2 (3 x 10 ml_), dried over MgSO4, filtered, and concentrated under reduced pressure to afford the crude material, which was purified by SiO2 flash column chromatography to give 0.17 g of the title compound 187 and 4-chloro-7-(5-fluoro-2-pyridinyl)-6,7-dihydro-5/-/-pyrrolo[2,3- c/]pyrimidine as an inseparable mixture . 1H NMR (400 MHz, CDCI3): delta 8.62 (s, 1 H), 7.92 (d, J = 2.68 Hz, 1 H), 7.14 – 7.23 (m, 1 H), 6.37 (dd, J1 = 9.10 Hz, J2 = 3.39 Hz, 1 H), 4.60 (br. s, 1 H), 6.67 (q, J = 6.54 Hz, 2 H), 3.24 (t, J = 6.87 Hz, 2 H); LCMS (APCI): m/z 287 (M + H)+.

The synthetic route of 16019-33-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/8895; (2008); A1;,
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Reference of 56734-10-2, 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. 56734-10-2, name is 2-(Methylthio)-4-phenylpyrimidine, molecular formula is C11H10N2S, 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 68 2-Methylsulfonyl-4-phenylpyrimidine A solution of 2.02 g. of 2-methylthio-4-phenylpyrimidine in 50 ml. of methylene chloride is cooled in an ice bath with 4.33 g. of m-chloroperbenzoic acid being added portionwise. After standing at room temperature overnight, the reaction mixture is washed with a saturated potassium carbonate solution, separated, and dried over anhydrous sodium sulfate. The solution is passed through a short pad of hydrous magnesium silicate absorbent and the eluent is refluxed on a steam bath with addition of hexane until crystallization is induced. On cooling the desired compound is removed by filtration, m.p. 135.5-137 C. Rec. Trav. Chim. 93, 375 (1974), m.p. 135-135.5 C.

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 56734-10-2, 2-(Methylthio)-4-phenylpyrimidine.

Reference:
Patent; American Cyanamid Company; US4209621; (1980); A;,
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Related Products of 10320-42-0 ,Some common heterocyclic compound, 10320-42-0, molecular formula is C4H2ClN3O2, 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.

The first step: a vacuum 50mL reaction bottle is vacuumed three times, then added to the reaction bottle4-bromoaniline (172 mg, 1.0 mmol, 1.0 equiv), add 10.0 mL of dry acetonitrile and stir to 4-bromoaniline.Then 2-chloro-5-nitropyrimidine (0.1593 g, 1.0 mmol, 1.0 equiv) was added to the reaction flask. Whole mixture in nitrogenThe reaction was carried out under a gas pressure for 4-5 hours. The reaction is detected by TLC, and if the reaction of aniline is detected, it can be stopped.Stop the reaction. The experimental treatment is to drain the solution in the reaction; dissolve the solute in the reaction flask with ethyl acetate, and transfer toIn a 100 mL round bottom flask, add 2 mL (200-300 mesh) of silica gel to the round bottom flask for spin-drying (petroleum ether and acetic acid B).Ester) over silica gel in the column. Wait until the intermediate product is pale yellow crystal N-(4-bromophenyl)-5-nitropyrimidin-2-amine (260 mg, 88% yield)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10320-42-0, its application will become more common.

Reference:
Patent; Jinan University; Feng Pengju; Chen Tianfeng; Chen Junfeng; Huang Yifeng; (25 pag.)CN108148005; (2018); A;,
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Synthetic Route of 7627-44-3 ,Some common heterocyclic compound, 7627-44-3, molecular formula is C5H3Cl2IN2, 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.

[0230] A mixture of 2,4-dichloro-5-(iodomethyl)pyrimidine (1.50 g, 5.19 mmol), 2,6- difluoro-3,5-dimethoxyaniline (1.08 g, 5.71 mmol) in N,N-diisopropylethylamine (4 mL) was stirred at 80 °C for 2 hours. After being cooled to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was purified on silica gel (eluting with 0- 40percent EtOAc in DCM) to give 1.70 g of the desired product. LCMS calculated for C13H12C12F2N302 [M+Hj m/z: 350.0; Found: 350.0.

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. 7627-44-3, 2,4-Dichloro-5-(iodomethyl)pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; INCYTE CORPORATION; LU, Liang; WU, Liangxing; SHEN, Bo; YAO, Wenqing; (114 pag.)WO2016/134294; (2016); A1;,
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Related Products of 69034-12-4, 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. 69034-12-4, name is 2-Chloro-5-(trifluoromethyl)pyrimidine. A new synthetic method of this compound is introduced below.

To a solution of 2-chloro-5-(trifluoromethyl)pyrimidine (0.300 g, 1.64 mmol) in dimethoxyethane (9 mL) was added a 2 M aqueous solution of sodium carbonate (3.7 mL, 7.4 mmol) and (5-(tert-butyl)-2-(methoxymethoxy)phenyl)boronic acid (0.500 g, 2.14 mmol). The solution was degassed with nitrogen for five minutes and tetrakis(triphenylphosphine)palladium(0) (95 mg, 0.082 mmol) was added and the reaction mixture heated to 80 C. in a sealed vial for 16 hours. The cooled reaction mixture was partitioned between ethyl acetate (25 mL) and 1 M aqueous sodium hydroxide solution (25 mL), the organic phase separated, dried (Na2SO4), filtered and concentrated under reduced pressure to give a yellow syrup. The crude product was purified by chromatography on silica eluting with a solvent gradient of 0 to 100% ethyl acetate in hexanes to give 2-(5-(tert-butyl)-2-(methoxymethoxy)phenyl)-5-(trifluoromethyl)pyrimidine (0.25 g, 44% yield) as a colorless oil. HPLC/MS Rt=7.12 min, m/z 341.1 (M+H+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,69034-12-4, 2-Chloro-5-(trifluoromethyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Jacobus Pharmaceutical Company, Inc.; Heffernan, Gavin David; Jacobus, David Penman; Saionz, Kurt William; Schiehser, Guy Alan; Shieh, Hong-Ming; Zhao, Wenyi; US2014/135320; (2014); A1;,
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Electric Literature of 56844-12-3 ,Some common heterocyclic compound, 56844-12-3, molecular formula is C6H2BrClN2S, 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: Compound 1 (1.00 g, 4.01 mmol) was mixed with the benzylamine (12.03 mmol) and 1-butanol (3.5 mL) and agitated at 145 C for 18-24 h. Then the mixture was cooled to rt, diluted with water (50 mL) and diethyl ether (150 mL) or EtOAc (150 mL). After phase separation, the water phase was extracted with more diethyl ether (2 × 50 mL) or EtOAc (2 × 50 mL). The combined organic phases were washed with saturated aq NaCl solution (50 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo, before the crude oil was dried under reduced pressure to constant weight to remove excess benzylamine. The compounds were purified by silica-gel column chromatography or crystallized as specified for each individual compound

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,56844-12-3, its application will become more common.

Reference:
Article; Bugge, Steffen; Kaspersen, Svein Jacob; Larsen, Synne; Nonstad, Unni; Bj°rk°y, Geir; Sundby, Eirik; Hoff, Bard Helge; European Journal of Medicinal Chemistry; vol. 75; (2014); p. 354 – 374;,
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Adding a certain compound to certain chemical reactions, such as: 36315-01-2, 2-Amino-4,6-dimethoxypyrimidine, 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, Safety of 2-Amino-4,6-dimethoxypyrimidine, blongs to pyrimidines compound. Safety of 2-Amino-4,6-dimethoxypyrimidine

One pot procedure for the synthesis of 2-amino-5,7-dimethoxy [1,2, 4] triazolopyrimidine (ADTP) from 2-amino-4,6-dimethoxypyrimidine (ADP) 11. 9 g (0.075 mol) ADP was dissolved in 68 g ethyl acetate. 11 g (0.0825 mol) ethoxycarbonyl isothiocyanate was added within 20 min. at 78C (no exotherm). The mixture was stirred over 5 h at reflux (78-79C). 49.2 g (0.075 mol) hydroxylammonium sulfate (25 % solution in water) were added and the mixture heated to 71C (reflux aceotrope). 50 g (0.1 mol) diluted caustic soda (2 mot/1) was added within 1 h to establish the pH from 1.3 to 6.5 and hold at 6.5-7. 0 (offgas C02 and H2S, slightly exotherm). The mixture was stirred over 6 h under reflux (71C) for reaction completion. The mixture was cooled down over night to 20C. The product (ADTP) was filtrated and washed 3 times with each 25 g water to remove the salt (Na content after first wash 0.42 %, after second 0.20 %, after third 0.025 %). Finally the solid ADTP was dried. Yield : 91.1 % in respect to ADP, purity 95.3 % (quantitative HPLC assay).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,36315-01-2, 2-Amino-4,6-dimethoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BASF AKTIENGESELLSCHAFT; WO2005/63753; (2005); A1;,
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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. 633328-98-0, name is 5-Chloro-1H-pyrazolo[4,3-d]pyrimidine, molecular formula is C5H3ClN4, 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. name: 5-Chloro-1H-pyrazolo[4,3-d]pyrimidine

NaH in mineral oil (570 mg, 14 mmol) was slowly added at 0 C. to a solution of 5-chloro-1H-pyrazolo[4,3-d]pyrimidine (2.0 g, 13 mmol) and [beta-(trimethylsilyl)ethoxy]methyl chloride (2.40 mL, 13.6 mmol) in tetrahydrofuran (25 mL). After stirring at r.t. for 1 h, the reaction mixture was quenched by the addition of water and the resulting mixture was extracted with ethyl acetate. The organic phase was washed with brine and dried over sodium sulfate. The solvents were evaporated under reduced pressure and the crude product was purified by Biotage Isolera (2.36 g, 64%). LCMS calculated for C11H18ClN4OSi (M+H)+ m/z=285.1; found 285.2

With the rapid development of chemical substances, we look forward to future research findings about 633328-98-0.

Reference:
Patent; Incyte Corporation; Vechorkin, Oleg; Liu, Kai; Pan, Jun; Sokolsky, Alexander; Ye, Hai Fen; Ye, Qinda; Yao, Wenqing; Hummel, Joshua; (117 pag.)US2018/72741; (2018); A1;,
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Electric Literature of 5604-46-6, 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 5604-46-6, name is 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of 112a (253 mg, 1.1 mmol) and 112b (192 mg, 1.0 mmol) was added DMF (20 ml) and the reactionmixture was stirred at room temperature overnight. Thenpoured the mixture into ice/saturated sodium bicarbonatesolution (40 ml). The precipitated solid was collected by filtration and washed with watet The solid was taken in DMF (10 ml) and added gl. acetic acid (10 drops). Thereaction mixture was stirred at room temperature overnightand processed as above. The solid thus obtained (223 mg)was taken in dichloromethane (10 ml) and treated with DDQ (138 mg, 0.6 mmol) at room temperature for 1 hr. The reaction mixture was diluted with chloroform (30 ml) and washed with saturated sodium bicarbonate solution (50 ml). Separated the organic layer, and the aqueous layer was extracted with EtOAc (50 ml). Combined the organic layers, dried (Na2 SO4), filtered and concentrated to provide 11 2cwhich was taken further without any purification. Conversion of 112c (0.6 mmol) to required product 112 followed procedures described above (Procedure H, Step 3). Crude 112 thus obtained was treated with excess di-tert-butyl dicarbonate (440 mg), catalytic DMAP (10 mg) in THF (8ml) at room temperature, overnight. The reaction mixture was processed using EtOAc (50 ml) and brine (50 ml). The organic layer was separated, dried (Na2504), filtered and concentrated. The residue was purified using silica gel (prepacked, 40 g cartridge) with 20/80 to 70/30 of EtOAc/ hexanes. This resulted in 32 mg of product containing two t-boc groups. This material was deprotected with 4M HC1 in dioxane (5 ml) at room temperature, overnight. The reaction mixture was concentrated, and the residue purified using silica gel (prepacked, 12 g cartridge) with 1/99 to 12/88 of MeOH/chloroform to provide 6 mg of 112 as a light brown solid.

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 5604-46-6, 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde.

Reference:
Patent; Merck Sharp & Dohme Corp.; Southern Research Institute; Arasappan, Ashok; Njoroge, F. George; Kwong, Cecil D.; Ananthan, Subramaniam; Bennett, Frank; Velazquez, Francisco; Girijavallabhan, Vinay M.; Huang, Yuhua; Kezar, III, Hollis S.; Maddry, Joseph A.; Reynolds, Robert C.; Roychowdhury, Abhijit; Fowler, Anita T.; Secrist, III, John A.; Kozlowski, Joseph A.; Shankar, Bandarpalle B.; Tong, Ling; Kim, Seong Heon; MacCoss, Malcolm; Venkatraman, Srikanth; Verma, Vishal; (798 pag.)US9433621; (2016); B2;,
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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. 153286-94-3, name is 5-Ethynylpyrimidine, the common compound, a new synthetic route is introduced below. Product Details of 153286-94-3

To a mixture of (5)-3-(l-((6-amino-5-iodopyrimidin-4-yl)amino)ethyl)-8-ehloro- 2-phenylisoquinoim-l(2//)-one (50.8 mg, 0.0981 mmol), Cul (2.2 mg, 0.012 mmol), and Pd(PPh3)2Cl2 (14.3 mg, 0.020 mmol) in anhydrous DMF (2 ml) was added 5-ethynylpyrimidine (31.6 mg, 0.304 mmol), and followed by the addition of tri ethyl amine (0.05 mL, 0.40 mmol). The resulted solution was heated to 75 C and stirred further for 5 hours, then cooled to rt, and quenched with water (15 mL), The resulted mixture was extracted with DCM (30 mL x 3), and the combined organic phases were washed with saturated brine (20 mL), dried over anhydrous Na2S04, and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/MeOH (v/v) :::: 100/5) to give the title compound as a yellowish solid (30 mg, yield 41.3%). MS (ESI, pos. ion) m/z: 494.2 [M+H]+; FontWeight=”Bold” FontSize=”10″ H NMR (600 MHz, OMSO-de) delta (ppm): 9.12 (d, J = 6.4 Hz, 2H), 7.89 (s, 1H), 7.60 (d, J = 3.9 Hz, 2H), 7.55-7.32 (m, 7H), 6.88 (d, J = 6.7 Hz, 2H), 6.75 (s, 1H), 4.75-4.61 (m, 1H), 1.33 (d, 3H).

The synthetic route of 153286-94-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD.; XI, Ning; WANG, Liang; WANG, Tingjin; WU, Weibin; (123 pag.)WO2015/175579; (2015); A1;,
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