Pyrimidines

Electric Literature of 56844-12-3, 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. 56844-12-3, name is 6-Bromo-4-chlorothieno[2,3-d]pyrimidine, molecular formula is C6H2BrClN2S, 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.

General procedure: Compound 1 (1.00 g, 4.02 mmol) was mixed with (4-fluorophenyl)boronic acid (4c) (844 mg, 6.03 mmol), fine powdered K2CO3 (1.68 g, 12.1 mmol), Pd2(dba)3 (186 mg, 0.20 mmol) and 1,4-dioxane (20 mL). The reaction was then stirred at 110 C for 26 h under N2 atmosphere. The solvent was removed and the product was dissolved in diethyl ether (150 mL) and washed with water (3 × 150 mL). The organic phase was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was absorbed onto silica and purified by silica-gel column chromatography (n-pentane/acetone, 19/1), Rf = 0.28. Drying gave 415 mg (1.57 mmol, 39%) of 24c as a pale white solid, mp 142-143 C; HPLC purity: 91% (method B), tR = 23.5 min; 1H NMR (400 MHz, DMSO-d6) delta: 8.93 (s, 1H), 8.04-7.98 (m, 3H), 7.43-7.36 (m, 2H); 13C NMR (100 MHz, DMSO-d6) delta: 167.6, 163.0 (d, J = 248.6), 153.3, 152.8, 144.1, 130.8, 129.2 (d, J = 8.7, 2C), 128.5 (d, J = 3.1), 116.5 (d, J = 22.0, 2C), 115.1; 19F NMR (564 MHz, DMSO-d6) delta: -115.3 (s); IR (neat, cm-1): 3063, 1884, 1505, 1429, 1228, 1165, 813, 759, 670; HRMS (ESI, m/z): 264.9995 (calcd. C12H735ClFN2S, 264.9997, [M + H]+).

According to the analysis of related databases, 56844-12-3, the application of this compound in the production field has become more and more popular.

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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Pyrimidine – Wikipedia

Related Products of 1197953-49-3 ,Some common heterocyclic compound, 1197953-49-3, molecular formula is C12H12Cl2N3OP, 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.

Synthesis of 5 (0798) A solution of 2 (1.0 eq), 4 (1.4 eq), and 2.5 M HCl in ethanol (excess) in 2-methoxyethanol was sealed and heated at 120 C. with stirring for 5.5 hours and then cooled to r.t. The reaction was repeated 5 times and combined. The mixture was filtered and evaporated. Saturated Na2CO3 was added, followed by DCM with stirring strongly. The layers were separated and the aqueous layer was extracted with DCM. The organics were dried, evaporated and chromatographed [EtOAc/MeOH (7M ammonia) 20:1] to give a yellow solid. EtOAc was added and the suspension was refluxed for 30 minutes. After cooled to r.t., filtration gave a solid, which was dissolved in DCM, filtered, and evaporated to afford 5 as an off-white solid (66% yield).

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. 1197953-49-3, (2-((2,5-Dichloropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; Wang, Yihan; Huang, Wei-Sheng; Liu, Shuangying; Shakespeare, William C.; Thomas, Ranny M.; Qi, Jiwei; Li, Feng; Zhu, Xiaotian; Kohlmann, Anna; Dalgarno, David C.; Romero, Jan Antoinette C.; Zou, Dong; US2015/225436; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 49845-33-2, name is 2,4-Dichloro-5-nitropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C4HCl2N3O2

Dichloro pyrimidine, 1, (0.34 g, 1.75 mmol) is combined with THF (4 mL) and stirred in an ice/salt water bath under N2 atmosphere. Methylamine (2.0 M in THF, 1.4 mL, 2.8 mmol) is added slowly to the stirring solution. After 10 minutes the mixture is diluted with H2O (20 mL) and extracted with EtOAc (2.x.50 mL). The combined organics are dried over MgSO4 and concentrated. The crude residue is purified over silica (0-10percent. EtOAc/hexanes) to afford 150 mg (46percent yield) or the desired product as a yellow oil. 1H NMR (300 MHz, CDCl3) delta 9.06 (s, 1H), 8.43 (br s, 1H), 3.25 (d, J=5.1 Hz, 3H); ESI/MS: 189 (M+H).

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, 49845-33-2, 2,4-Dichloro-5-nitropyrimidine.

Reference:
Patent; The Procter & Gamble Company; US7256196; (2007); B1;,
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Pyrimidine – Wikipedia

Application of 3001-72-7 , The common heterocyclic compound, 3001-72-7, name is 2,3,4,6,7,8-Hexahydropyrrolo[1,2-a]pyrimidine, molecular formula is C7H12N2, 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: In a pressure-resistant container equipped with a stirrer,162 parts (0.89 mol) of triethyl phosphate (manufactured by Nippon Synthetic Chemical Industry Co., Ltd.) (A-1)130 parts (1.78 mol) of diethylamine (manufactured by BASF) (B-1) were charged, and the temperature was raised to 125 C. The reaction was allowed to continue for 30 hours with stirring. After cooling, the P-NMR of the reaction solution was measured. As a result, the peak of triethyl phosphate disappeared and only the peak of diethyl phosphate appeared. 260 parts (0.9 mol) of a methanol solution of 1,2,3,4-tetramethylimidazolium methyl carbonate (J-1) was added to this reaction solution for salt exchange. This solution was concentrated under reduced pressure at 100 C. using a rotary evaporator to obtain a yellow-brown solid. It was confirmed by 1 H-NMR and P-NMR that this yellowish brown solid was 1,2,3,4-tetramethylimidazolium diethylphosphate (K-1). In Example 1, 260 parts of a 1,2,3,4-tetramethylimidazolinium methyl carbonate salt methanol solution was changed to 112 parts ((0.9 mol)) of 1,5-diazabicyclo [4.3.0] -5-nonene (E-1 ), a yellow brown liquid was obtained in the same manner as in Example 1. It was confirmed by 1 H-NMR and P-NMR that this yellow-brown solid was 1,5-diazabicyclo [4.3.0] -5-nonenium diethyl phosphate (F-1).

The synthetic route of 3001-72-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANYO CHEMICAL INDUSTRIES LIMITED; SHIRAISHI, ATSUSHI; (21 pag.)JP5647820; (2015); B2;,
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Pyrimidine – Wikipedia

Reference of 13223-25-1 , The common heterocyclic compound, 13223-25-1, name is 2-Chloro-4,6-dimethoxypyrimidine, molecular formula is C6H7ClN2O2, 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.

4-(2-Bromophenyl)piperazine-1-carboxylic acid tert-butyl ester (280 mg, 0.82 mmol),4,6-Dimethylpyrimidin-2-amine (151 mg, 1.23 mmol),Sodium tert-butoxide (0.16 g, 1.16 mmol), tris(dibenzylideneacetone) dipalladium (75 mg, 0.082 mmol) and(±)-2,2′-bis-(diphenylphosphino)-1,1′-binaphthyl (102 mg, 0.164 mmol) was added to anhydrous tolueneIn (20 mL), the reaction was heated to 120 C for 12 hours under a nitrogen atmosphere. The reaction was stopped, and the mixture was cooled to room temperature. The mixture was poured into water (100 mL), ethyl acetate (40 mL×3), and the organic phase was combined and washed with water (50 mL) and brine (50 mL) Dry and distill off the solvent under reduced pressure.The obtained crude product was subjected to column chromatography (dichloromethane:methanol (V:V)=50:1)The title compound (white solid, 274 mg, 87%)

The synthetic route of 13223-25-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jin Chuanfei; Zhang Yingjun; Xue Yaping; Guo Zhengjiang; (39 pag.)CN109912514; (2019); A;,
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Adding a certain compound to certain chemical reactions, such as: 55583-59-0, 2,5-Diamino-4,6-dichloropyrimidine, 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, SDS of cas: 55583-59-0, blongs to pyrimidines compound. SDS of cas: 55583-59-0

General procedure: To a solution of pyrimidine (100 mg, 1 equivalent) in anhydrous dioxane (2 mL/mmol) under argon atmosphere, were successively added the amine (1 equivalent) and APTS.H2O (0.5 equivalent). The solution was stirred at reflux for 6h and then allowed to reach room temperature. A 0.2 M solution of corresponding dimethyliminium chloride (2 to 3 equivalents) in anhydrous DMF, or a 0.2 M solution of POCl3 or oxalyl chloride (1.5 to 3 equivalents) in corresponding N,N-dimethylamide was then added dropwise and the resulting mixture was stirred for another hour. Water (5 mL/mmol) was then slowly added and the resulting mixture was stirred at room temperature for 18h. The solution was diluted in AcOEt (5 mL/mmol) and washed with a saturated aqueous solution of NaHC03 (5 mL/mmol). The aqueous layer was extracted 3 times with AcOEt and the resulting organic layer was then dried over magnesium sulfate. After concentration under reduced pressure, the crude product was purified by chromatography on silica gel to afford the pure compound.

The synthetic route of 55583-59-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITE GRENOBLE ALPES; DECOUT, Jean-Luc; ZELLI, Renaud; ZEINYEH, Wael; BOUCHERLE, Benjamin; HAUDECOEUR, Romain; (53 pag.)WO2018/203099; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 2380-63-4, 1H-Pyrazolo[3,4-d]pyrimidin-4-amine, 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, Computed Properties of C5H5N5, blongs to pyrimidines compound. Computed Properties of C5H5N5

Step 2A mixture of lH-pyrazolo[3,4-d]pyrimidm-4-amine (150 g, 1.1 1 mo., 1.00 equiv) and N-iodo-succinimide (375 g, 1.67 mol, 1.58 equiv) in N,N-dimethylformamide (2.5 L) was stirred at 80C for 5 h. The reaction mixture was cooled to room temperature and then diluted with 10 L of water. The solid was collected by filtration, washed with 2 1 L of saturated aqueous sodium sulfite and dried under vacuum to give 50 g (52%) of 3-iodo-lH- pyrazolo[3,4-d]pyrimidin-4-amine as a yellow solid.

The synthetic route of 2380-63-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PRINCIPIA BIOPHARMA INC.; GOLDSTEIN, David Michael; BRAMELD, Kenneth Albert; WO2012/158795; (2012); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 5413-85-4, 5-Amino-4,6-dichloropyrimidine, 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, 5413-85-4, blongs to pyrimidines compound. Formula: C4H3Cl2N3

A suspension of 5-Amino-4,6-dichloropyrimidine (3 g, 0.02 mol) in ammonia (25 mL, 7N/MeOH, 0.175 mole) was heated at 118 C. overnight (under pressure). The reaction was cooled to 23 C., filtered and washed with ethanol to obtain 1.92 g (70%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5413-85-4, its application will become more common.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2008/51404; (2008); A1;,
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Pyrimidine – Wikipedia

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. 131860-97-4, name is (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate. A new synthetic method of this compound is introduced below., category: pyrimidines

Methyl (£)-2-{2-[6-chloropyiimidin-4-yloxy]phenyl}-3-methoxyacrylate (E) (3g of 95.4% strength) was charged to the reaction tube followed by the solvent (10 ml) then 2- cyanophenol (1.2g), base (1.5 mol equivalents) and the compound being tested as a catalyst (15 mol%). The reaction mixtures were held, with stirring, at 400C for 4hrs, then at 6O0C for 2 hrs. The reaction was monitored for formation of product, throughout the hold period, by Gas Chromatography. Results are recorded as area % levels of methyl (£)-2-{2-[6- chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (II) and methyl (E)-2-{2-[6-(2- cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (I) in the reaction mixture.The following systems were tested:TABLE l The results are shown in Table 2 below:TABLE 2

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, 131860-97-4, (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate.

Reference:
Patent; SYNGENTA LIMITED; WO2008/43977; (2008); A1;,
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Pyrimidine – Wikipedia

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. 36314-97-3, name is 2-Amino-4-chloro-6-phenylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

Examples 19-22; Using the following general method, Examples 19-22 were prepared; A suspension of Intermediate A (1.0 mmol), Intermediate B (1.0 mmol), and HCl (0.1 mL) in H2O (1.0 mL) was heated to 70 C. in a 5 mL reaction vial overnight. The reaction mixture was diluted with MeOH, treated with saturated NaHCO3, coated on silica and purified by MPLC (Biotage) with 5% MeOH in CH2Cl2.; Example 19; Preparation of N-(2-amino-6-phenyl-4-pyrimidinyl)-N-[3,5-dichloro-4-(4-pyridinylsulfanyl)phenyl]amine; Prepared in 40% yield from A17 and B14: TLC (4% MeOH in CH2Cl2) Rf 0.42; MS (ES) 440 [M+H]+; 1H-NMR (DMSO-d6) delta6.53 (s, 1H), 6.67 (bs, 2H), 6.94 (d, J=6.1 Hz, 2H), 7.47-7.51 (m, 3H), 7.93-7.96 (m, 2H), 8.18 (s, 2H), 8.36 (d, J=5.7 Hz, 2H), 9.88 (bs, 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, 36314-97-3, 2-Amino-4-chloro-6-phenylpyrimidine.

Reference:
Patent; BAYER CORPORATION; US2004/2508; (2004); A1;,
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Pyrimidine – Wikipedia