Pyrimidines

Adding a certain compound to certain chemical reactions, such as: 75833-38-4, 2-Chloropyrimidine-4-carbonitrile, 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, 75833-38-4, blongs to pyrimidines compound. name: 2-Chloropyrimidine-4-carbonitrile

2-Chloropyrimidine-4-carbonitrile (22.42 mg, 0.161 mmol), Na2C03 (134 muEpsilon, 0.268 mmol), (S)-3-(4-(6-amino-5-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2- yl)pyridin-3-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (65mg, 0.134 mmol), and dichloro(l,l-bis(diphenylphosphinoferrocene))palladium(II) (10.94 mg, 0.013 mmol) were combined in dioxane (268 mu) and stirred at 100C in a microwave oven for 1 hour. LC-MS indicated good conversion to desired product. After cooling to room temperature, the reaction mixture was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (12 g), eluting with a gradient of 0 % to 10 % MeOH in DCM, to provide (S)-2-(2-amino-5-(4- (5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)phenyl)pyridin-3-yl)pyrimidine-4- carbonitrile as yellow solid. NMR (500 MHz, DMSO-d6) delta 10.56 (s, 1H), 8.83 (d, J = 4.70 Hz, 1H), 8.59 (d, J= 2.67 Hz, 1H), 8.13 (d, J= 8.44 Hz, 1H), 8.06 (dd, J= 2.14, 6.30 Hz, 1H), 7.66 (d, J= 8.66 Hz, 2H), 7.58 (d, J= 8.87 Hz, 2H), 7.49 (d, J= 4.49 Hz, 1H), 7.35 – 7.42 (m, 2H), 7.23 – 7.35 (m, 3H), 5.49 (s, 1H), 1.66 (s, 3H), 0.92 (s, 3H). m/z (ESI) 463.8 (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,75833-38-4, its application will become more common.

Reference:
Patent; AMGEN INC.; BREGMAN, Howard; BUCHANAN, John, L.; CHAKKA, Nagasree; DIMAURO, Erin; GUNAYDIN, Hakan; GUZMAN PEREZ, Angel; HUA, Zihao; HUANG, Hongbing; HUANG, Xin; MARTIN, Matthew, W.; PATEL, Vinod; WO2013/134079; (2013); A1;,
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Related Products of 1979-96-0, 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. 1979-96-0, name is 4,6-Dichloro-2-(methylthio)-5-nitropyrimidine, molecular formula is C5H3Cl2N3O2S, 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.

Method VII, Part 1: 4-Amino-6-chloro-2-methylthio-5-nitropyrimidine: To a solution of above dichloride (2.46 g, 10.2 mmol) in THF (34 mL) at -20 C. was added Et3N (3.14 mL, 22.5 mmol) followed by a solution of NH3 (2.0 M in MeOH, 5.4 mL, 11 mmol). The mixture was stirred while warming to 0 C. for 1.5 h (LC/MS indicated consumption of starting materials. Some bis-addition is observed). The reaction mixture was taken forward without work-up.

According to the analysis of related databases, 1979-96-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gilead Sciences, Inc.; US2010/143301; (2010); A1;,
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Synthetic Route of 4595-60-2, 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 4595-60-2 as follows.

General procedure: A dry, argon-flushed Schlenk flask equipped with a magnetic stirring bar and a septum was charged with spiro compound 1 (0.38 mmol. 1.0 equiv) in anhyd THF (3 mL) and cooled to -78 C for 10 min. 2.48M n-BuLi in hexane (0.42 mmol, 1.1 equiv) was added and the mixture was stirred at -78 C for 1 h until GC analysis of reaction aliquots showed full consumption of the starting material. 1 M ZnCl2 in THF solution (0.46 mmol, 1.2 equiv) was added and the mixture was stirred at -78 to 0 C for 1 h. An aryl bromide or acid chloride 10d-o(0.30 mmol, 0.8 equiv) and Pd(PPh3)4 (0.015 mmol, 0.05 equiv, 5mol%) were added and the mixture was stirred at 50 C for 3-6 h. The mixture was quenched with sat. aq NH4Cl solution (5 mL) and extracted with EtOAc (4 × 15 mL). The combined organic phases were dried (Na2SO4) and concentrated in vacuo. The crude residue obtained was purified by flash column chromatography (silica gel pre-neutralizedwith Et3N, isohexane-EtOAc) to give the analytically pure spiroproduct 11d-o.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4595-60-2, its application will become more common.

Reference:
Article; Dhayalan, Vasudevan; Alcaniz, Fernando Rabasa; Werner, Veronika; Karaghiosoff, Konstantin; Knochel, Paul; Synthesis; vol. 47; 24; (2015); p. 3972 – 3982;,
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Reference of 878650-31-8, 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 878650-31-8, name is Methyl 2,6-dichloro-5-methoxypyrimidine-4-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Example 6 Preparation of methyl 6-amino-2-chloro-5-methoxy-pyrimidine-4-carboxylate (Head C) A solution of methyl 2,6-dichloro-5-methoxy-pyrimidine-4-carboxylate (25 g, 0.1 mol) and dimethyl sulfoxide (DMSO) was prepared. To this solution was added, at 0-5 C., a solution of ammonia (2 equivalents (equiv) in DMSO). This mixture was stirred at the same 0-5 C. temperature for 10 to 15 min. Later, the mixture was diluted with ethyl acetate, and the resulting solid was filtered off. The ethyl acetate filtrate was washed with a brine solution and dried over sodium sulfate. Upon concentration, the crude product was obtained. The crude product was stirred in a minimum amount of ethyl acetate and filtered to obtain the pure compound. Additional pure compound was obtained from the filtrate which, after concentration, was purified by flash chromatography. This produced the title compound (11 g, 50%): mp 158 C.; 1H NMR (DMSO-d6) delta 3.71 (s, 3H), 3.86 (s, 3H), 7.65 (brs, 1H), 8.01 (brs, 1H).

According to the analysis of related databases, 878650-31-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dow AgroSciences LLC; ECKELBARGER, Joseph D.; EPP, Jeffrey B.; FISCHER, Lindsey G.; GIAMPIETRO, Natalie C.; KISTER, Jeremy; PETKUS, Jeffrey; ROTH, Joshua; SATCHIVI, Norbert M.; SCHMITZER, Paul R.; SIDDALL, Thomas L.; YERKES, Carla N.; US2014/274703; (2014); A1;,
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Related Products of 126728-20-9, 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. 126728-20-9, name is 2,4-Dichloropyrido[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below.

General procedure: To a solution of 2,4-dichlorofuro[3,2-d]pyrimidine (la) (0.71 g, 3.74 mmol; CAS 956034- 07-4) in 2-Propanol (20 mL) was added DIPEA (1.63 mL, 9.36 mmol), 1-methyl-1H-imidazol-4-amine hydrochloride (0.5 g, 3.74 mmol) and heated at reflux for 24 h. The reaction mixture was concentrated in vacuum to dryness and the residue obtained was triturated with water. The solid obtained was collected by filtration and dried in vacuum to afford 2-chloro-N-(l-methyl-lH-imidazol-4-yl)furo[3,2-d]pyrimidin-4-amine (lb) (550 mg,59 % yield) as brown solid; NMR (300 MHz, DMSO-^) delta 10.89 (s, 1H, D20exchangeable), 8.35 (d, J = 2.1 Hz, 1H), 7.52 (d, J = 1.6 Hz, 1H), 7.39 (d, J = 1.3 Hz, 1H), 7.03 (d, J = 2.1 Hz, 1H), 3.71 (s, 3H); MS (ES+): 250.3 (M+l), 272.3, 274.3 (M+Na), (ES-): 248.2 (M-l).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,126728-20-9, 2,4-Dichloropyrido[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
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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 146533-41-7, name is 5-(4-Bromophenyl)-4,6-dichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 5-(4-Bromophenyl)-4,6-dichloropyrimidine

f) A solution of 4,6-dichloro-5-(4-bromophenyl)-pyrimidine (405 mg, 1.33 mmol) and 3-benzyloxypropylsulfamide potassium (752 mg, 2.66 mmol) in DMSO is stirred at rt under argon for 18 h. The clear solution is poured onto 10% aq. citric acid solution (50 mL) and extracted twice with EA (2×75 mL). The organic extracts are washed with water (50 mL) and the solvent is evaporated. The residue is purified by column chromatography on silica gel eluting with hexane/EA 3:2 to afford 1-benzyloxypropanesulfamic acid [6-chloro-5-(4-bromophenyl)-pyrimidin-4- yl]-amide (524 mg) as a colourless foam. LC-MS: tR = 1.05 min, [M+H]+ = 510.96; 1H NMR (CDCI3): delta 8.44 (s, 1H), 7.71-7.65 (m, 2H), 7.40-7.28 (m, 5H), 7.18-7.12 (m, 2H), 6.90 (s, 1H), 6.05 (t, J = 5.9 Hz, 1 H), 4.49 (s, 2H), 3.57 (t, J 0 5.9 Hz, 2H), 3.18 (q, J = 5.9 Hz, 2H), 1.88 (p, J = 5.9 Hz, 2H).

With the rapid development of chemical substances, we look forward to future research findings about 146533-41-7.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2006/51502; (2006); A2;,
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Related Products of 1374639-77-6 , The common heterocyclic compound, 1374639-77-6, name is (2-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)methanol, molecular formula is C12H14ClN3O, 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.

To a mixture of (2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)methanol (IVa) (4.5 g) and tert-butyl 4-(6-aminopyridin-3-yl)piperazine-l-carboxylate (Va) (4.97 g) in methyl isobutyl ketone (36 mL) was added palladium (II) acetate (0.08 g) and 2,2′- bis(diphenylphosphino)-l, l’-binaphthyl (0.44 g) at 25-30 C. The reaction mass was then heated to 40 C. Cesium carbonate (8.73 g) was added to the above reaction mass portion wise at 40 C. The reaction mass was heated to 100 C and stirred for 3 hours. The reaction mass was cooled to 70 C. Water (36 mL) was added to the above reaction mass at 70 C and again cooled to 50 C. n-Heptane (54 mL) was added to the above reaction mass drop wise at 50 C. The reaction mass was again cooled to 20 C and stirred for 2 hours at the same temperature. Resulting solid compound was then filtered, washed with ^-Heptane (2 chi 10 mL) and dried for 4 hours at 50 C to afford title compound. (0163) Yield: 5 2 g; Purity by HPLC: 97 01 %

The synthetic route of 1374639-77-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DR. REDDY?S LABORATORIES LIMITED; PEDDIREDDY, Subba Reddy; KOTTUR, Mohan Kumar; ORUGANTI, Srinivas; KANDAGATLA, Bhaskar; DAS GUPTA, Shirshendu; (39 pag.)WO2018/51280; (2018); A1;,
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Reference of 33034-67-2, 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. 33034-67-2, name is 2-Chloro-4-(trifluoromethyl)pyrimidine. A new synthetic method of this compound is introduced below.

Step 1 : A solution of 3-bromo-5-methylaniline (162.5 g, 873.66 mmol) in 1,4- dioxane (2 L) was prepared, and 2-chloro-4-(trifluoromethyl)pyrimidine (182 g, 994.54 mmol) and methanesulfonic acid (97.5 g, 1.02 mol) were added sequentially. The resulting solution was heated to reflux overnight. The resulting mixture was cooled and concentrated in vacuo. The residue was diluted with 2 L of water, then adjusted to pH 7-8 with aqueous sodium bicarbonate solution, followed by extraction with EtOAc (2 x 2 L). The organic layers were combined, washed with water (2x 2 L), dried over anhydrous sodium sulfate and concentrated in vacuo. This resulted in N-(3-bromo-5-methylphenyl)-4-(trifluoromethyl)pyrimidin-2-amine as a light yellow solid. MS(ESI): [M + 3]+ 334.0. NMR (400 MHz, CDC13): delta 8.68 (d, J = 4.9 Hz, 1 H); 7.79 (s, l H); 7.30 (s, 2 H); 7.10-7.06 (m, 2 H); 2.36 (s, 3 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,33034-67-2, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; HAIDLE, Andrew, M.; BURCH, Jason; GUAY, Daniel; GAUTHIER, Jacques Yves; ROBICHAUD, Joel; FOURNIER, Jean Francois; ELLIS, John Michael; CHRISTOPHER, Matthew; KATTAR, Solomon, D.; SMITH, Graham; NORTHRUP, Alan, B.; WO2014/31438; (2014); A2;,
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Reference of 3934-20-1, 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. 3934-20-1, name is 2,4-Dichloropyrimidine. A new synthetic method of this compound is introduced below.

In a N2 atmosphere at 0 C for 10 minutes,CH3MgBr (3M in diethyl ether, 22.68 mL,68.03 mmol) was added dropwise to a stirred solution of 1-H-indole (7.97 g, 68.03 mmol) in 1,2-dichloroethane (250 mL).The resulting solution was stirred for 15 minutes and then 2,4-dichloropyrimidine (15.00 g, 100.69 mmol) was added in one portion. The resulting solution was allowed to warm to room temperature and stirred for additional 16 hours.The reaction was quenched by the addition of CH 3OH (25 mL) and then the mixture was concentrated in vacuo and applied to silica gel. Purification by FCC,Elution with 0-20% CH3OH in CH2Cl2,The title compound (7.17 g, 46%)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3934-20-1, 2,4-Dichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Jiao Yuqi; (26 pag.)CN108929311; (2018); A;,
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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.115617-41-9, name is 4,5-Dichloro-6-ethylpyrimidine, molecular formula is C6H6Cl2N2, molecular weight is 177.03, as common compound, the synthetic route is as follows.Formula: C6H6Cl2N2

Example D 5-Chloro-6-ethyl-4-[cis-2-(4-methylphenyl)-1,3-dithian-5-ylamino]-pyrimidine 1.77 g (10 mmol) of 4,5-dichloro-6-ethyl-pyrimidine and 2.2 g (10 mmol) of 5-amino-2-(4-methylphenyl)-1,3-dithian were stirred with 2.02 g of triethylamine at 80-90 C. for 6 hours. The mixture was taken up in water/methylene chloride and the organic phase was dried and concentrated. For purification, the residue was chromatographed over silica gel (eluding agent petroleum ether/ethyl acetate 4:1). This gave 1.0 g of colorless solid (27.3% of theory), melting point: 138-139 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,115617-41-9, 4,5-Dichloro-6-ethylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Hoechst Scering AgrEvo GmbH; US6281221; (2001); B1;,
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