Category: pyrimidines

Related Products of 56741-94-7, 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. 56741-94-7, name is 2-Amino-6-phenylpyrimidin-4(3H)-one, molecular formula is C10H9N3O, 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.

A suspension of guanidine carbonate (3.60 g, 20 mmol) in ethanol (120 mL) and toluene (20 mL) was refluxed under nitrogen for 1 h, during which time about 50 mL of solvent was removed by distillation. After the mixture was cooled to 45 0C, ethyl 3-oxo-3- phenylpropanoate (7.68 g, 40 mmol) was added and the solution was heated at reflux overnight. The desired product precipitated as a white solid during the reaction. Water (50 mL) was added to the reaction and the mixture was refluxed for an additional 30 min. After cooling to rt, the mixture was neutralized with IN HCl and placed in the refrigerator for 6 h. The solid was filtered, washed with water followed by ether and dried at 60 0C under vacuum to give the product as white solid (6.45 g, 86%). MS ES: 188 (M+H)+, calcd 188; RT = 0.91 min; TLC (CH2Cl2/ 2M NH3 in MeOH 95/5) Rf = 0.10.A mixture of the above product (6.0 g, 32 mmol) and POCl3 (100 mL) was heated at reflux for 1 h. The majority of the POCl3 was removed in vacuo and the residue was diluted with EtOAc and poured over an ice/saturated NaHCO3 solution. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with brine, dried (Na2SO4), and concentrated. The crude organic concentrate was re-crystallized from EtO Ac/ether to give the product IA as an off-white powder (2.8 g, 43%). MS ES: 206 (M+H)+, calcd 206; RT = 2.49 min; TLC (CH2Cl2/ 2M NH3 in MeOH 95/5) Rf = 0.72. (Reference 1: H. L. Skulnick, S. D. Weed, E. E. Edison, H. E. Renis, W. Wierenga, and D. A. Stringfellow, J. Med. Chem. 1985, 28, 1854-1869).

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 56741-94-7, 2-Amino-6-phenylpyrimidin-4(3H)-one.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2006/99231; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 150010-20-1, 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.150010-20-1, name is 2-Bromo-5-methylpyrimidine, molecular formula is C5H5BrN2, molecular weight is 173.0106, as common compound, the synthetic route is as follows.

To a mixture of compound 7-3 (80 mg, 0.24 mmol) and 2-bromo-5- methylpyrimidine (46 mg, 0 27 mmol ) in DMT (2 mL) was added potassium carbonate (67 mg, 0.48 mmol) and 18-crown-6 (64 mg, 0.24 mmol) and the mixture was stirred at 100 C for 16 hours. The mixture was diluted with EtOAc and washed with saturated aqueous NEUCl solution and brine, dried over anhydrous NarSCX filtered and concentrated to dryness. The residue was purified by chromatography on silica gel (eluted with PE: EtOAc 2: 1) to afford compound 7-4 (47 mg, yield 45.9 %) as a yellow solid. LC/MS (ESI) m/z: 423 (M+H)?.

Statistics shows that 150010-20-1 is playing an increasingly important role. we look forward to future research findings about 2-Bromo-5-methylpyrimidine.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; GAHHACHANDA, Venkat, Rao; EASTMAN, Kyle, J.; GODWIN, Pais; (611 pag.)WO2020/51532; (2020); A2;,
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Synthetic Route of 1119280-68-0, Adding some certain compound to certain chemical reactions, such as: 1119280-68-0, name is 2-Chlorothieno[3,2-d]pyrimidine,molecular formula is C6H3ClN2S, 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 1119280-68-0.

To a solution of 2-chlorothieno[3,2-d]pyrimidine (150mg, 0.87mmol) and 4- morpholinoaniline (188mg, 1.05mmol) in NMP (5mL) was added diisopropylethylamine (337muL, 1.93mmol). The reaction was heated at 25O 0C in a microwave reactor for 20min, then diluted with EtOAc and 5%aq. citric acid. The aqueous layer was extracted twice further with EtOAc and the combined organic fractions washed with sat. aq. NaHCO3, dried (Na2SO4) filtered and concentrated to afford the crude product. Purification by silica gel chromatography using 30-70% EtOAc/DCM as eluent then afforded the product as an orange gum. Trituration with EtOAc three times and collection of the fine solid afforded compound 7 as a dark yellow solid (26mg, 10%).

According to the analysis of related databases, 1119280-68-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CYTOPIA RESEARCH PTY LTD; WO2009/62258; (2009); A1;,
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Reference of 42754-96-1, 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. 42754-96-1, name is 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine, molecular formula is C5H2Cl2N4, 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.

Step B: 4-(2,6-Dimethyl-4-(pyridin-4-yl)phenoxy)-6-chloro-1H-pyrazolo[3,4-d]pyrimidine; Sodium hydride (1.2 eq) is added to 2,6-dimethyl-4-(pyridin-4-yl)phenol (prepared according to literature procedures, see Combellas et al., Tetrahedron Letters, 1992, 33, 4923) (1.2 eq) in 1-methyl-2-pyrridone (2 ml/mmol) at 0 C. The reaction mixture is stirred at room temperature for 30 min and a solution of-4,6-dichloro-1H-pyrazolo[3,4-d]pyrimidine (1 eq) in 1-methyl-2-pyrridone (1 ml/mmol) is added. The resulting mixture is heated to 100 C. for 16 h, cooled to room temperature, poured into ice water and extracted with CHCl3 (×3). The combined organic layers are washed with water and brine, dried (Na2SO4), concentrated to dryness and purified by silica gel chromatography.

According to the analysis of related databases, 42754-96-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ardea Biosciences; US2009/162319; (2009); A1;,
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Synthetic Route of 6972-27-6, 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. 6972-27-6, name is 6-Chloro-1,3-dimethylpyrimidine-2,4(1H,3H)-dione, molecular formula is C6H7ClN2O2, 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.

3-[4-(2-Methoxyphenyl)piperazin-1-yl]propylamine (50.00 g, 0.20 mol) was added to a 500 ml clean three-neck reaction flask.And 6-chloro-1,3-dimethyluracil purified water(35.01g, 0.20mol), anhydrous sodium carbonate (63.59g, 0.60mol)And purified water (500ml), mechanically stirred, heated to 60 C for 2 hours,The temperature was lowered to room temperature, suction filtered, and the filter cake was blast dried at 50 C for 6 hours to obtain 66.23 g of urapidil.The yield was 85.2% and the purity was 97.9%.

According to the analysis of related databases, 6972-27-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hebei Yipin Pharmaceutical Co., Ltd.; Zhang Ji; Chen Wenhui; Lv Shuai; Liu Xuesong; Duan Shibao; Li Minghao; Cheng Yao; Zhao Cuiran; Zhang Yongran; (7 pag.)CN109516960; (2019); A;,
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Electric Literature of 1780-40-1, 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.1780-40-1, name is 2,4,5,6-Tetrachloropyrimidine, molecular formula is C4Cl4N2, molecular weight is 217.8682, as common compound, the synthetic route is as follows.

To a solution of 2,4,5, 6-tetrachloropyrimidine (1 kg, 4.63 mol) in THF (6 L) was added IN NaOH (6 L, 6.0 mol) drop wise, and the mixture was stirred overnight at room temperature. The solution was acidified with IN HC1 and extracted with DCM (3x). The combined organics were dried (Na2S04) and concentrated in vacuo. The solids were slurried in Et20 for 30 min, filtered, washed with Et20 and dried to give 635 g (69%) of the title compound. LCMS (C18 column, column size: 4.6*50 mm; mobile phase: 20%-40%, Acetonitrile-Water-0.02% NH4OAc): Rt= 2.785 min; [M+H] Calc’d for C4HC13N20, 199; Found, 199.

Statistics shows that 1780-40-1 is playing an increasingly important role. we look forward to future research findings about 2,4,5,6-Tetrachloropyrimidine.

Reference:
Patent; CELGENE QUANTICEL RESEARCH, INC.; CHEN, Young K.; KANOUNI, Toufike; KALDOR, Stephen W.; STAFFORD, Jeffrey Alan; VEAL, James Marvin; TAVARES-GRECO, Paula Alessandra; KREILEIN, Matthew Michael; (41 pag.)WO2017/79670; (2017); A1;,
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Reference of 13223-25-1 ,Some common heterocyclic compound, 13223-25-1, 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.

2-Chloro-4,6-dimethoxypyrimidine (50 g, 0.29 mol) was suspended in trifluoroacetic anhydride (175 ml, 1.24 mol, 4 equiv.) and the mixture was cooled in a brine-ice bath to +2 0C. Concentrated nitric acid was then added drop-wise to the stirred mixture (CARE; effervescence and exotherm) at such a rate that the exotherm did not cause the temperature of the reaction mixture to rise above +40 0C (about 45 minutes). After 1 hour the reaction was complete (as determined by TLC of an aliquot which was quenched with water and extracted with DCM; plate eluted with DCM). The resulting thick white precipitate was poured onto ice (500 g) and the aqueous solution was extracted with dichloromethane (2 x 400 ml). The combined organic layers were then washed with saturated aqueous sodium bicarbonate solution (2 x 200 ml) until the washings remained at pH 7. The solution was dried (MgSO4) and the solvent was removed under reduced pressure to give a yellow- white crystalline solid. This material was partially dissolved in warm diethyl ether (~300ml) with stirring and then cooled in an ice-bath. Filtration gave the product as a pale yellow-white crystalline solid (56 g, 88 %).; 2-Chloro-4,6-dimethoxypyrimidine (2 g, 11.5 mol) was suspended in trifluoroacetic anhydride (3.2 ml, 23 mmol, 2 eq.) and the mixture was cooled in a brine ice-bath to +2 0C. Fuming nitric acid (0.58 ml, 13.8 mmol, 1.2 eq) was then added drop-wise to the stirred mixture (exotherm) at such a rate that the exotherm did not cause the temperature of the reaction mixture to rise above +40 0C (about 1 minute). The thick precipitate was then warmed to room temperature and left overnight. After this time the reaction was complete (as determined by TLC of an EPO aliquot which was quenched with water and extracted with DCM; TLC run with DCM and visualised with uv). Water (20 ml) was added to the resulting thick white precipitate and the aqueous solution was extracted with dichloromethane (2 x 40 ml). The combined organic layers were then washed with saturated aqueous NaHCO3 solution (-20 ml) until the washings remained at pH 7, dried (MgSO4) and the solvent was removed under reduced pressure to give a white crystalline solid (2.38 g, 95 %).

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. 13223-25-1, 2-Chloro-4,6-dimethoxypyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PARADIGM THERAPEUTICS LTD.; WO2007/582; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1546-78-7, 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. 1546-78-7, name is 4-Hydroxy-6-(trifluoromethyl)pyrimidine, molecular formula is C5H3F3N2O, 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.

Preparation of 6-Trifluoromethyl-pyrimidin-4-ylamine; The procedure was derived from methods described in US 5,756,275 and WO 02/38569. In a 250 mL round bottom flask, 6-trifluorornethyl-4-pyrimidinol (10 g, 60.9 mmol) was dissolved in 70 mL phosphorus oxychloride (0.73 mol). The solution was heated at reflux for 7 h. The cooled reaction solution was then added gradually to 200 mL 30% ammonium hydroxide, and the resulting mixture was stirred overnight at room temperature. The reaction mixture was extracted with ethyl acetate (2 x 100 mL), and the combined extracts were dried (MgSO4) and evaporated in vacuo to give 6-trifluoromethyl-pyrimidin-4-ylami?e (1.4 g, yield 14%) as a white solid. 1H NMR (400 MHz, DMSO-dbeta) delta 8.50 (s, 1 H), 7.60 (broad s, 2 H), 6.90 (s, 1 H); LC-MS m/z 164.1 [M+Hf.

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 1546-78-7, 4-Hydroxy-6-(trifluoromethyl)pyrimidine.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2007/75650; (2007); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 941685-26-3, 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine, 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, blongs to pyrimidines compound. Recommanded Product: 941685-26-3

A solution of 4-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3- fif]pyrimidine (15.0 g, 52.9 mmol) in N,N-dimethylformamide (200 mL) was added to Pd(dppf)Cl2 (2.2 g, 2.7 mmol), (3-nitrophenyl)boronic acid (13.3 g, 79.7 mmol) under nitrogen. A solution of sodium carbonate (6.00 g, 56.6 mmol) in water (60.0 mL) was then added and the reaction was stirred for 3 hours at 100 C. The resulting mixture was concentrated in vacuo, and the solids were filtered and extracted with dichloromethane (*3). The combined organic layers were washed with H20, brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The reaction was then purified by chromatography using silica gel, eluting with 0-33% EtOAc/petroleum ether. The product was collected and concentrated in vacuo to afford 4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-£ lpyrirnidine as a yellow solid. LRMS (ESI) calc’d for [M+H]+: 371, found 371.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,941685-26-3, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; AHEARN, Sean, P.; CHRISTOPHER, Matthew; JUNG, Joon; PU, Qinglin; RIVKIN, Alexey; SCOTT, Mark, E.; WITTER, David, J.; WOO, Hyun Chong; CASH, Brandon; DINSMORE, Christopher; GUERIN, David; WO2013/85802; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 374930-88-8 ,Some common heterocyclic compound, 374930-88-8, molecular formula is C13H19BrN4O2, 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.

tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate (0.242 g, 0.705 mmol) was taken up in THF (3.5 mL) and cooled to -78 C. A solution of nBuLi, 2.5 M in hexanes (0.31 mL, 0.775 mmol) was added at a fast dropwise rate from a syringe. The resulting mixture was stirred at -78 C. for 15 minutes. A solution of (R,Z)-2-methyl-N-(2,2,2-trifluoro-1-(4-fluorophenyl)ethylidene)propane-2-sulfinamide (0.225 g, 0.762 mmol) in THF (0.5 mL) was added at a fast dropwise rate from a syringe. The reaction mixture was stirred at -78 C. for 5 minutes before warming to room temperature. After 45 minutes, saturated NH4Cl was added and the products extracted into EtOAc (×2). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification of the residue by MPLC (0-80% EtOAc-hexanes) gave tert-butyl 4-(5-((S)-1-(((R)-tert-butylsulfinyl)amino)-2,2,2-trifluoro-1-(4-fluorophenyl)ethyl)pyrimidin-2-yl)piperazine-1-carboxylate (304 mg, 0.543 mmol, 77% yield) as a pale yellow gum. The absolute stereochemistry was assigned randomly. MS (ES+) C25H33F4N5O3S requires: 559. found: 560 [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,374930-88-8, its application will become more common.

Reference:
Patent; Hodous, Brian L.; Kim, Joseph L.; Wilson, Kevin J.; Wilson, Douglas; Zhang, Yulian; US2015/111887; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia