Pyrimidines

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. 582313-57-3, name is 4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below., Recommanded Product: 4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine

4.1.11 7-(2-O-Acetyl-3,5-di-O-benzyl-4-C-methyl-beta-d-ribofuranosyl)-4-chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine (12) To a slurry of 4-chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine 11 (2.06 g, 12 mmol) in dry MeCN (20 ml) was added N,O-bis(trimethylsilyl)acetamide [BSA] (2.94 ml, 9.55 mmol) and the mixture was stirred at rt for 15 min (clear solution). Then a solution of 1,2-di-O-acetyl-3,5-di-O-benzyl-4-C-methyl-beta-d-ribofuranose 5 (5.14 g, 12 mmol) in MeCN (40 ml) was added, followed by TMSOTf (4.34 ml, 24 mmol). The solution was stirred at 80 ¡ãC for 3 h. After cooling, the mixture was diluted with EtOAc (200 ml), cautiously washed with saturated aq NaHCO3 (100 ml) and aqueous phase was re-extracted with EtOAc (2 * 25 ml). Combined organic phases were dried (MgSO4), concentrated in vacuo and loaded on silica by co-evaporation. Column chromatography (SiO2, hexane-AcOEt, 10:1) afforded nucleoside 12 as yellowish oil (3.76 g, 58percent). 1H NMR (500 MHz, CDCl3): 1.32 (s, 3H, CH3-4′); 2.05 (s, 3H, CH3CO); 3.40 (d, 1H, Jgem = 10.2 Hz, H-5’a); 3.56 (d, 1H, Jgem = 10.2 Hz, H-5’b); 4.42 (d, 1H, J3′,2′ = 5.7 Hz, H-3′); 4.48 (bd, 1H, Jgem = 11.5 Hz, CH2a-Bn-5′); 4.50 (d, 1H, Jgem = 11.5 Hz, CH2a-Bn-3′); 4.56 (d, 1H, Jgem = 11.5 Hz, CH2b-Bn-5′); 4.60 (d, 1H, Jgem = 11.6 Hz, CH2b-Bn-3′); 5.56 (bt, 1H, J2′,3′ = J2′,1′ = 5.3 Hz, H-2′); 6.62 (dd, 1H, J1′,2′ = 5.0 Hz, J1′,F = 1.8 Hz, H-1′); 7.29-7.41 (m, 11H, H-o,m,p-Bn-3′,5′, H-6); 8.59 (s, 1H, H-2). 13C NMR (125.7 MHz, CDCl3): 18.99 (CH3-4′); 20.69 (CH3CO); 73.64 (CH2-Bn-5′); 74.18 (CH2-Bn-3′); 74.43 (CH2-5′); 75.97 (CH-2′); 77.79 (CH-3′); 85.00 (CH-1′); 86.30 (C-4′); 107.58 (d, JC,F = 14.4 Hz, C-4a); 109.64 (d, JC,F = 27.0 Hz, CH-6); 127.86 and 127.97 (CH-o-Bn-3′,5′); 128.03 and 128.11 (CH-p-Bn-3′,5′); 128.45 and 128.62 (CH-m-Bn-3′,5′); 137.21 (C-i-Bn-5′); 137.57 (C-i-Bn-3′); 141.60(d, JC,F = 253.6 Hz, C-5); 147.04 (d, JC,F = 1.2 Hz, C-7a); 150.46 (d, JC,F = 3.7 Hz, C-4); 151.50 (CH-2); 169.93 (CO). 19F NMR (470.3 MHz, DMSO-d6): -167.38 (s, 1F, F-5). IR (ATR): nu 1678, 1622, 1593, 1457, 1231, 1070, 1028, 741, 700 cm-1. MS (ESI) m/z 540 (M+H), 562 (M+Na). HRMS (ESI) for C28H27O5N3ClFNa [M+Na] calcd: 562.15155; found: 562.15140.

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, 582313-57-3, 4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Article; Nau?, Petr; Caletkova, Olga; Perlikova, Pavla; Po?tova Slav?tinska, Lenka; Tlou??ova, Eva; Hodek, Jan; Weber, Jan; D?ubak, Petr; Hajduch, Marian; Hocek, Michal; Bioorganic and Medicinal Chemistry; vol. 23; 23; (2015); p. 7422 – 7438;,
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Electric Literature of 5305-59-9, 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. 5305-59-9, name is 6-Chloropyrimidin-4-amine, molecular formula is C4H4ClN3, 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.

The 200 mg (1equiv) 4-amino-6-chloro-pyrimidine, 152 mg (1.2equiv) 4-methyl imidazole, 604 mg (1.2equiv) adding cesium carbonate flask, 10mLN, N ‘-dimethyl formamide as a solvent, the temperature is increased to 120 C, reaction 12h. Adding proper amount of water, extraction with ethyl acetate, saturated salt water washing, drying by anhydrous sodium sulfate, filter, evaporate solvents under reduced pressure, the residue is purified by silica gel column chromatography separation, methanol/dichloromethane = 1/20 elution, to get the yellow solid 176 mg, yield 65%.

According to the analysis of related databases, 5305-59-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; East China University of Technology; Mao, Fei; Wang, Huan; Li, Xiaokang; Zhang, Haiyan; Lu, Zhengyu; Li, Jian; (43 pag.)CN105418592; (2016); A;,
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Adding a certain compound to certain chemical reactions, such as: 3764-01-0, 2,4,6-Trichloropyrimidine, 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 C4HCl3N2, blongs to pyrimidines compound. Computed Properties of C4HCl3N2

Take 5000ml three necked flask, equipped with mechanical stirrer, condenser. Feed: 18.2 g of 2,4,6-trichloropyrimidine (molecular weight 182,0.10 mol), phenylboronic acid 28.1 g (molecular weight 122,0.23 mol), tetrakis(triphenylphosphine)palladium 12.0g (0.0104mol), potassium carbonate 60 g (0.435 mol), tetrahydrofuran 600 ml, toluene 400 ml, water 400 ml. Mechanical agitation was initiated under conditions of reduced pressure ventilation Ar gas three times to maintain protection, monitoring the reaction by TLC (thin layer chromatography), refluxed for 8 hours, the reaction was complete. Allowed to cool, the reaction system was divided into two layers, the organic layer was separated and evaporated to dryness to give a solid product, which was recrystallized from toluene to give intermediate M3-1 was 19.9 g, molecular weight 266, 75% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3764-01-0, 2,4,6-Trichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Kunshan Visionox Display Technology?Co., Ltd; Tsinghua University; Beijing Visionox Technology Co. Ltdk; QIU, YONG; TANG, JINMING; FAN, HONGTAO; DUAN, LIAN; REN, XUEYAN; (97 pag.)CN103664906; (2016); B;,
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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. 33034-67-2, name is 2-Chloro-4-(trifluoromethyl)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2-Chloro-4-(trifluoromethyl)pyrimidine

General procedure: alpha,beta-unsaturated tosylhydrazones 1 (0.11 mmol, 1.1 equiv), heteroaryl chlorides 2 (0.1 mmol, 1 equiv), Cs2CO3 (0.25 mmol, 2.5 equiv) and MeCN (1 mL) were added to a tube. The mixture was stirred at 60 C until the heteroaryl chlorides was completely disappeared for 4-8h. After cooling to room temperature, the mixture was quenched with NH4Cl (2 mL, saturated aqueous solution) and extracted with CH2Cl2 (3 ¡Á 2 mL). The combined organic phases were dried over Na2SO4 and solvents removed in vacuo. The residue was purified by flash column chromatography on silica gel with ethyl acetate/petroleum ether (1:10-1:4, V/V) as the eluent, affording the desired product 3 and 4.

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, 33034-67-2, 2-Chloro-4-(trifluoromethyl)pyrimidine.

Reference:
Article; Zeng, Lin; Guo, Xiao-Qiang; Yang, Zai-Jun; Gan, Ya; Chen, Lian-Mei; Kang, Tai-Ran; Tetrahedron Letters; vol. 60; 33; (2019);,
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Adding a certain compound to certain chemical reactions, such as: 6299-85-0, Methyl 2,6-dichloropyrimidine-4-carboxylate, 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, Recommanded Product: Methyl 2,6-dichloropyrimidine-4-carboxylate, blongs to pyrimidines compound. Recommanded Product: Methyl 2,6-dichloropyrimidine-4-carboxylate

Example 226 (Z)-methyl 2-(((1-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)pyrimidin-2-yl)piperidin-4-yl)methyl)amino)pyrimidine-4-carboxylate was prepared as follows.Methyl 2-((piperidin-4-ylmethyl)amino)pyrimidine-4-carboxylate was prepared as follows: A 40 mL round-bottomed vial was charged with tert-butyl 4-(aminomethyl)piperidine-1-carboxylate (1.76 mmol, 1.1 equiv.), acetonitrile (4 mL), DiPEA (2.37 mmol, 1.5 equiv.), methyl 2,6-dichloropyrimidine-4-carboxylate (1.58 mmol, 1 equiv.), and then shaken at 85 C. for 72 h. The reaction mixture was concentrated under reduced pressure and purified on SiO2 using a Biotage and a 10-50% EtOAc/hexanes gradient to provide the desired protected amine (233 mg, 552 mg theoretical, 42%). Methyl 2-((piperidin-4-ylmethyl)amino)pyrimidine-4-carboxylate was prepared using the general TFA de-protection procedure and used directly in the general displacement procedure to provide the title compound (4 mg, 73.4 mg theoretical, 5%). LC-MS m/z 456.1 (M+1).

The synthetic route of 6299-85-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jasco Pharmaceuticals, LLC; US2011/152235; (2011); A1;,
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Application of 14048-15-8 , The common heterocyclic compound, 14048-15-8, name is 2,4-Dimethoxypyrimidin-5-amine, molecular formula is C6H9N3O2, 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.

Reference Example 95 5-Isothiocyanato-2,4-dimethoxypyrimidine To a solution of 2,4-dimethoxypyrimidin-5-amine (prepared by the method described in U.S. Pat. No. 6,342,503B1) (4.68 g, 30.0 mmol) in tetrahydrofuran (60 mL) was added 1,1-thiocarbonyldiimidazole (6.41 g, 36.0 mmol) portionwise at 0 C. The mixture was warmed to room temperature and stirred for 20 hr. The mixture was concentrated in vacuo to give a residue which was passed through a pad of silica gel eluding with n-hexane/ethyl acetate. The filtrate was concentrated in vacuo to give the title compound (5.0 g, 84%) as a colorless solid. 1H NMR (CDCl3) delta 3.99 (s, 3H), 4.09 (s, 3H), 8.06 (s, 1H). MS Calcd.: 197; Found: 198 (M+H).

The synthetic route of 14048-15-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/186879; (2009); A1;,
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Reference of 3934-20-1 ,Some common heterocyclic compound, 3934-20-1, molecular formula is C4H2Cl2N2, 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 2,4-Dichloropyrimidine (1.0 g, 6.7 mmol) was added 28 % w/v ammonium hydroxide solution (20 mL). The mixture was stirred overnight at ambient temperature then concentrated in vacuo. The residue was dry loaded and purified by FCC eluting with 2-10 % EtOH in CHCI3 to afford 2-amino-4-chloropyrimidine and 2-chloro-4-aminopyrimidine. Yield: 2-amino-4-chloropyrimidine 200 mg, 23 %; 2-chloro-4-aminopyrimidine 600 mg, 69 %.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3934-20-1, its application will become more common.

Reference:
Patent; EVOTEC NEUROSCIENCES GMBH; MADDEN, James; HALLETT, David James; PARKES, Alastair; RAOOF, Ali; WANG, Xialou; WO2010/20556; (2010); A1;,
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Electric Literature of 17321-93-6, 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. 17321-93-6, name is 2-Amino-5-bromo-4-methylpyrimidine, molecular formula is C5H6BrN3, 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.

Isoamylnitrite (21ML) was added to a stirred suspension of 5-bromo-4-methyl-2- PYRIMIDINAMINE (1.75g) in bromoform (30ML) and the mixture heated at 85¡ãC for 4h. After cooling, isohexane (300ML) was added and the solution passed through a pad of silica-gel. The silica was washed with petrol (1000ml), dichloromethane (200ml) then the product eluted with ethylacetate. The ethylacetate layer was evaporated under reduced pressure and the residue purified by chromatography on silica eluting with 5percent diethylether/ isohexane, yield 0. 9g 1H NMR CDC13 : No. 8. 52 (s, 1H), 2.64 (s, 3H) MS: APCI (-VE) 249/51/53

According to the analysis of related databases, 17321-93-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; WO2004/89885; (2004); A1;,
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Pyrimidine – Wikipedia

Reference of 90213-66-4, 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. 90213-66-4, name is 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below.

To a suspension of 2.4-dichloro-7H–pvrro]o[2,3-dipyrimidine (7.2 g, 38 rnmoi) in DCM (120 mL) was added N4odosuccinimide (12.0 g. 53.3 rnmol) in portions over 30 mm. The mixture was stirred at 25 C for 16 h. The mixture was filtered, the filtered cake was washed with DCM to give 2,4-dichioro-5-iodo–7H-pyrroio[2,3-d]pyrimidine (131a) (76 g, 24 mmoi, 64% yield) as a white solid. LCMS [M-FF{]: 3139.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,90213-66-4, 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; PRELUDE THERAPEUTICS, INCORPORATED; LUENGO, Juan; LEAL, Raul, A.; LIN, Hong; SHETTY, Rupa; (166 pag.)WO2018/85833; (2018); A2;,
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Synthetic Route of 24415-66-5 ,Some common heterocyclic compound, 24415-66-5, molecular formula is C6H5ClN4, 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 4 (50 mg; 0.296 mmol), Na2CO3 (60.74 mg; 0.592 mmol), Pd(PPh3)4 (34.66 mg; 0.030 mmol) and boronic acid (1.5 equiv.) was heated at 130 C in dioxane/water (4/1, 3 mL) for 3h. The reaction was followed by TLC. After completion, the mixture was filtered by celite and concentrated under vacuum. The solid obtained was submitted to a column chromatography. The increase of polarity in solvent gradient was made from neat petroleum ether to mixture of AcOEt/petroleum ether (6:4).

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. 24415-66-5, 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Loubidi, Mohammed; Moutardier, Anais; Campos, Joana F.; Berteina-Raboin, Sabine; Tetrahedron Letters; vol. 59; 11; (2018); p. 1050 – 1054;,
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