Tag: M.W:100-200

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.4316-97-6, name is 4,6-Dichloro-5-methylpyrimidine, molecular formula is C5H4Cl2N2, molecular weight is 163.01, as common compound, the synthetic route is as follows.HPLC of Formula: C5H4Cl2N2

To a solution OF 4-HYDROXY-PIPERIDINE-1-CARBOXYLIC acid isopropyl ester (6.26 g, 33.4 mmol) and 4,6-dichloro-5-methyl-pyrimidine (5.45 g, 33.4 mmol) in 100 mL THF, 1M potassium TERT- butoxide in THF (40 mL, 40 mmol) were added slowly by syringe pump. After 1 hour, everything had been added and mixture was concentrated. Residue was extracted with methylene chloride and water. Organic phases were dried over magnesium sulfate, filtered, and concentrated to give 4- (6- CHLORO-5-METHYL-PYRIMIDIN-4-YLOXY)-PIPERIDINE-1-CARBOXYLIC acid isopropyl’ester as a pale yellow solid (10.3 g, 98%). H NMR (CDC13, 400 MHz) 8 1.22-1. 24 (d, 6H), 1.74-1. 81 (M, 2H), 1.95-2. 04 (M, 2H), 2.24 (s, 3H), 3.40-3. 45 (M, 2H), 3.74-3. 81 (M, 2H), 4.90-4. 98 (M, 1H), 5.31-5. 37 (M, 1H), 8.40 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4316-97-6, 4,6-Dichloro-5-methylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2005/7647; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 2227-98-7, 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. 2227-98-7, name is 4-Aminopyrrolo[3,2-d]pyrimidine. A new synthetic method of this compound is introduced below.

[0065] (4S)-4-{[l-(Triphenylmethyl)-lH-imidazol-4-yl]methyl}-l,3-oxazolidin-2-one or (4S)-4-{[l-(triphenylmethyl)-lH-imidazol-5-yl]methyl}-l,3-oxazolidin-2-one (P.l). A modified literature procedure [Madrigal, et al.14] was followed. (5)-Histidinol dihydrochloride (0.500 g, 2.34 mmol) and diethyl carbonate (2.86 mL, 23.61 mmol) were stirred together in ethanol (24 mL), then sodium methoxide in methanol solution (25%, 1.6 mL, 7.0 mmol) added. The mixture was heated under reflux for 72 h then the solvent was evaporated and the residue chromatographed on silica gel (CHCl3-MeOH-28% aq. NH4OH, 9: 1:0.1) to give (45)-4-(lH-imidazol-4-ylmethyl)-l,3-oxazolidin-2-one as a colourless solid (0.26 g, 1.56 mmol, 90 – 95% pure). XH NMR (500 MHz, CD3OD): delta 7.61 (d, J = 1.0 Hz, 1H), 6.93 (s, 1H), 4.45-4.40 (m, 1H), 4.18-4.12 (m, 2H), 2.86 (dd, J= 14.7, 4.8 Hz, 1H), 2.80 (dd, J= 14.8, 6.1 Hz, 1H). It was dissolved in DMF (4 mL) then triethylamine (0.42 mL, 3.00 mmol) and trityl chloride (0.489 g, 1.70 mmol) were added. The mixture was stirred for 60 h at rt then diluted with Et20 (60 mL) and the mixture washed with H20 (4 x 5mL), brine (5 mL), dried and the solvent evaporated. The residue was chromatographed on silica gel (gradient of 0 – 5% MeOH in EtOAc) to give P.l as a colourless foam (0.520 g, 54%). XH NMR (500 MHz, CD3OD): delta 7.41 (d, J = 1.4 Hz, 1H), 7.39-7.34 (m, 9H), 7.16-7.1 1 (m, 6H), 6.82 (m, 1H), 4.39 (t, J = 8.4 Hz, 1H), 4.19-4.11 (m, 2H), 2.78 (dd, J = 14.6, 4.9 Hz, 1H), 2.73 (dd, J = 14.6, 6.1 Hz, 1H). 13C NMR (125.7 MHz, CD3OD, centre line delta 49.0): delta 162.1 (C), 143.6 (C x 3), 139.8 (CH), 136.6 (C), 130.9 (CH), 129.32 (CH), 129.27 (CH), 121.6 (CH), 76.9 (C), 70.4 (CH2), 53.4 (CH), 33.9 (CH2). ESI-HRMS calcd for C26H23N3Na02+, (M+Na)+, 432.1683, found 432.1677. [0066] (2S)-2-Amino-3-[l-(triphenylmethyl)-lH-imidazol-4-yl]propan-l-ol or (2S)-2- amino-3-[l-(triphenylmethyl)-lH-imidazol-5-yl]propan-l-ol (P.2). Compound P.l (0.510 g, (0109) I .25 mmol) was dissolved in 2-propanol (7 mL) and potassium hydroxide (2 M, 3 mL, 6 mmol) added. The mixture was heated at 80 C for 6 h then silica gel was added to absorb all the solvent then the solvent was evaporated and the residue chromatographed on silica gel (CHCl3-MeOH-28% aq. NH4OH, 9: 1 :0.1) to give P.2 as a colourless gum (0.478 g, 100%). XH NMR (500 MHz, CD3OD): delta 7.40 (d, J = 1.4 Hz, 1H), 7.38-7.34 (m, 9H), 7.18-7.13 (m, 6H), 6.75 (m, 1H), 3.52 (dd, J= 10.9, 4.5 Hz, 1H), 3.35 (dd, J = 10.9. 6.8 Hz, 1H), 3.09-3.03 (m, 1H), 2.65 (dd, J = 14.4, 6.0 Hz, 1H), 2.50 (dd, J = 14.4, 7.4 Hz, 1H). 13C NMR (125.7 MHz, CD3OD, centre line delta 49.0): delta 143.7 (C), 139.7 (CH), 139.2 (C), 130.8 (CH), 129.3 (CH), 129.2 (CH), 121.0 (CH), 76.8 (C), 66.7 (CH2), 53.8 (CH), 33.0 (CH2). ESI-HRMS calcd for C25H26N30+, (M+H)+, 384.2071, found 384.2068. [0067] (2S)-2-[({4-Amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl}methyl)amino]-3-[l- (triphenylmethyl)-lH-imidazol-4-yl]propan-l-ol or (2S)-2-[({4-amino-5H-pyrrolo[3,2- d]pyrimidin-7-yl} methyl)amino] -3 – [ 1 -(triphenylmethyl)- 1 H-imidazol-5-yl]propan- 1 -ol (P.3). Compound P.2 (0.200 g, 0.52 mmol), 9-deazaadenine (0.070 g, 0.52 mmol) and aq. formaldehyde solution (37%, 0.051 mL, 0.68 mmol) were heated at 70 C in tert-butanol (3 mL) forl6 h. Silica gel was added to absorb all the solvent then the solvent was evaporated and the residue chromatographed on silica gel (10% 7M NH3/MeOH-CHCl3) to give P.3 as a colourless foam (0.101 g, 37%). XH NMR (500 MHz, CD3OD): delta 8.03 (s, 1H), 7.39 (s, 1H), 7.35 (d, J = 1.3 Hz, 1H), 7.33-7.29 (m, 9H), 7.12-7.08 (m, 6H), 6.75 (d, J = 1.2 Hz, 1H), 3.96 (d, J = 13.7 Hz, 1H), 3.93 (d, J = 13.6 Hz, 1H), 3.61 (dd, J = 1 1.3, 4.8 Hz, 1H), 3.49 (dd, J = (0111) I I.3, 6.1 Hz, 1H), 3.02-2.97 (m, 1H), 2.72 (dd, J = 14.5, 6.5 Hz, 1H), 2.69 (dd, J = 14.5, 6.7 Hz, 1H). C NMR (125.7 MHz, CD3OD, centre line delta 49.0): delta 152.0 (C), 150.8 (CH), 146.6 (C), 143.7 (C x 3), 139.5 (CH), 139.2 (C), 130.8 (CH), 129.24 (CH), 129.20 (CH), 128.9 (CH), 121.2 (CH), 115.4 (C), 114,8 (C), 76.8 (C), 64.3 (CH2), 59.4 (CH), 41.3 (CH2), 30.7 (CH2). ESI-HRMS calcd for C32H32 70+, (M+H)+, 530.2663, found 530.2666. [0068] (2S)-2-[({4-Amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl}methyl)amino]-3-(lH- imidazol-4-yl)propan-l-ol (PA). Trifluoroacetic acid (0.6 mL, 8 mmol) was added to a stirred solution of P.3 (0.100 g, 0.19 mmol) and triethylsilane (0.090 mL, 0.57 mmol) in CH2CI2 (3 mL). After 2 h, the solvent was evaporated and the residue dissolved in MeOH and the solvent evaporated (3 x). The residue was again dissolved in MeOH, silica gel added and the solvent evaporated. Flash chromatography on silica gel (CHCl3-MeOH-28% aq. NH4OH, 7:2.5:0.5) gave P.4 as a colourless gum which crystallized on standing (0.050 g, 92%). XH NMR (500 MHz, CD3OD): delta 8.14 (s, 1H), 7.52 (d, J= 0.9 Hz, 1H), 7.42 (s, 1H), 6.80 (s, 1H), 4.01 (d, J= 13.6 Hz, 1H), 3.98 (d, J= 13.6 Hz, 1H), 3.63 (dd, J= 11.3, 4.7 Hz, 1H), 3.50 (dd, (0113) J = 11.3, 5…

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2227-98-7, 4-Aminopyrrolo[3,2-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ALBERT EINSTEIN COLLEGE OF MEDICINE OF YESHIVA UNIVERSITY; SCHRAMM, Vern, L.; CLINCH, Keith; GULAB, Shivali, Ashwin; WO2015/123101; (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. 22536-66-9, name is 2-Chloropyrimidine-4-carboxamide. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C5H4ClN3O

Methyl (2-(methylamino)ethyl)carbamic acid tert-butyl ester (1.88 g, 9.99 mmol), 2-chloropyrimidine-4-carboxamide (1.73 g, 10.98 mmol) and potassium carbonate under nitrogen. (1.52g, 10.98mmol) was added toN,N-dimethylformamide (15 mL).The reaction mixture was warmed to 130 C, stirred for 20 hr then cooled to room temperature, filtered and evaporated. The resulting residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate (v / v) = 1/1) to afford the title compound as a white solid (2.50g, 81.0%).

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, 22536-66-9, 2-Chloropyrimidine-4-carboxamide.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jin Chuanfei; Xu Xianjie; Zhang Yingjun; Zheng Changchun; (42 pag.)CN105085491; (2019); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1780-26-3, 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. 1780-26-3, name is 2-Methyl-4,6-dichloropyrimidine, molecular formula is C5H4Cl2N2, 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.

Compound 32a is prepared according to the procedure described in US/2006/0004067A1 (Bang-Chi Chen, et al, published Jan. 05, 2006).

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 1780-26-3, 2-Methyl-4,6-dichloropyrimidine.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/219370; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 2557-79-1, 6-Methyl-2-(trifluoromethyl)pyrimidin-4(3H)-one, 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, 2557-79-1, blongs to pyrimidines compound. Product Details of 2557-79-1

EXAMPLE VI O,O-Diethyl O-(6-methyl-2-(trifluoromethyl)-4-pyrimidinyl)phosphate STR9 A mixture of 3.6 g of 6-methyl-2-(trifluoromethyl)-4-pyrimidinol, 5.0 g of finely powdered potassium carbonate, 40 ml of acetonitrile and 3.45 g of O,O-diethyl chlorophosphate was stirred and heated under reflux for one hour. At this time, no more of the starting phosphorus compound could be detected by glc. The salts were removed by filtration and the filtrate concentrated under reduced pressure. The residue was taken up in ether, the ether solution washed twice with 5 percent aqueous sodium hydroxide solution, once with saturated sodium chloride solution and dried over anhydrous sodium sulfate. The ether was removed in a rotary evaporator leaving 4.0 g of the above-indicated product as an amber colored oil having a refractive index of nd25 =1.4327. The IR and NMR spectra were in agreement with the desired structure. Upon analysis, the product was found to have carbon, hydrogen and nitrogen contents of 38.41, 4.57 and 9.11 percent, respectively, as compared with the theoretical contents of 38.22, 4.49 and 8.92 percent, respectively, as calculated for the above-named structure (Compound 6).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2557-79-1, its application will become more common.

Reference:
Patent; The Dow Chemical Company; US4575499; (1986); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 5177-27-5, 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. 5177-27-5, name is 5-Amino-2,4-dichloropyrimidine, molecular formula is C4H3Cl2N3, 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 round-bottomed flask equipped with a magnetic stirrer was added 2,4-dichloropyrimidin-5-amine (1.89 g, 11.52 mmol), DIPEA (8.05 ml, 46.1 mmol), morpholine-3-carboxylic acid (1.66 g, 12.68 mmol), and DMSO (5 ml). The reaction was stirred at 100 C. overnight. The reaction mixture was poured into water and extracted with EtOAc 3 times. The pH of the aqueous layer was adjusted (about 5) with 10% citric acid and extracted again with EtOAc. The combined organic layer dried over MgSO4, filtered, and concentrated in vacuo to furnish a tan solid. The solid was triturated in diethyl ether containing a small amount of EtOH, filtered, and dried to give 2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one: 1.95 g (70.3%). MS [M+H] found 241.

According to the analysis of related databases, 5177-27-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2011/53921; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 116247-92-8, 1-Pyrimidin-2-yl-piperidin-4-one, 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 C9H11N3O, blongs to pyrimidines compound. Computed Properties of C9H11N3O

To a solution of LDA (prepared from diisopropylamine (167.4 mg, 1.658 mmol) and n-BuLi (2.5 M in hexanes, 0.663 ml, 1.658 mmol) at -78 C., was added a solution of the above 1-pyrimidin-2-yl-piperidin-4-one (320 mg, 1.382 mmol). The mixture was stirred at the same temperature for 1 hour, followed by the addition of PhNTf2 (543.1 mg, 1.52 mmol). The reaction mixture was warmed up to room temperature and stirred for 3 hours before it was quenched with the addition of saturated ammonium chloride (15 ml) and EtOAc (40 ml). After separation of the layers, the aqueous phase was extracted with EtOAc (2*10 ml). The combined organic layers were washed with brine (10 ml), dried (MgSO4), filtered, and concentrated under reduced pressure to furnish the crude product. This material was purified by column chromatography (20% EtOAc/hexanes) to give the corresponding triflate (210.7 mg, 49%) as a white solid as long with recovered starting material (142.9 mg): 1H NMR (CDCl3, 400 MHz) delta 8.37 (d, J=6.4 Hz, 2 H), 6.59 (t, J=6.4 Hz, 1 H), 5.91 (m, 1 H), 4.41 (m, 2 H), 4.11 (t, J=5.6 Hz, 2 H), 2.55 (m, 2 H); MS calc’d for C10H11F3N3O3S [M+H]+: 310; Found: 310.

The synthetic route of 116247-92-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Barbosa, Joseph; Dong, Li; Fink, Cynthia Anne; Wang, Jiancheng; Zipp, G. Gregory; US2006/258672; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 4318-56-3, 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 4318-56-3, name is 6-Chloro-3-methylpyrimidine-2,4(1H,3H)-dione. This compound has unique chemical properties. The synthetic route is as follows.

Isobutyl bromide (8.90 mL, 82.2 mmol) was added to a solution of 6-chloro-3-methyluracil (4) (12.0 g, 74.7 mmol) and potassium carbonate (12.4 g, 89.7 mmol) in DMSO (120 mL). The mixture was then heated to 60 C and stirred for 48 h. The mixture was then cooled to room temperature and diluted with water (40 mL) and brine (40 mL). The product was then extracted using diethyl ether (3×40 mL). The organic layers were combined, dried (MgSO4), filtered and concentrated in vacuo to provide title compound 6 (13.7 g, 84%) as an orange oil. This was used directly in the next step without further purification. Spectroscopic data were consistent with the literature.17 1H NMR (400 MHz, CDCl3) delta 0.96 (6H, d, J=6.8Hz, CH(CH3)2), 2.11-2.22 (1H, m, 2?-H), 3.34 (3H, s, 3-CH3), 3.90 (2H, d, J=7.6Hz, 1?-H2), 5.92 (1H, s, 5-H); 13C NMR (101 MHz, CDCl3) delta 19.7 (2×CH3), 28.1 (CH3), 28.3 (CH), 53.5 (CH2), 101.9 (CH), 146.0 (C), 151.2 (C), 160.9 (C); MS (CI) m/z 217 (M+H+, 95%), 183 (17), 69 (10).

According to the analysis of related databases, 4318-56-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; O’Rourke, Kerry M.; Johnstone, Erin S.; Becker, Holger M.; Pimlott, Sally L.; Sutherland, Andrew; Tetrahedron; vol. 74; 30; (2018); p. 4086 – 4094;,
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. 89793-12-4, name is Ethyl 2-chloropyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 89793-12-4

To a solution of compound 4 (2.29 g 10 mmol) in dioxane (50 ml) was added compound 5 (1.87 g, 1.0 equiv.) and DIPEA (2.58 g, 2.0 equiv.). The mixture was heated overnight at 110-120° C. The resulting mixture was directly purified on silica gel column to afford the coupled product, compound 6, as a white solid (1.37 g, 40percent).

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, 89793-12-4, Ethyl 2-chloropyrimidine-5-carboxylate.

Reference:
Patent; Acetylon Pharmaceuticals, Inc.; Quayle, Steven Norman; Jones, Simon Stewart; US2015/105383; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 7431-45-0, 2-Phenylpyrimidine, 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, 7431-45-0, blongs to pyrimidines compound. category: pyrimidines

General procedure: [Cp*RhCl2]2 (2.5 mol %), Cu(OTf)2 (5 mol %), 1a (0.2 mmol), 2a (0.6 mmol, 3 equiv) and DCE (2 mL) were added to a test tube. The reaction mixture was stirred at 90 oC for 12 h. After that, the solvent was removed under reduced pressure and the residue was purified by silica gel chromatography using PE/EA (5:1) to afford the title compound 4a.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7431-45-0, its application will become more common.

Reference:
Article; Jin, Chen; Wang, Guimin; Yang, Xueyan; Zhu, Weiliang; Yang, Yaxi; Tetrahedron Letters; vol. 59; 21; (2018); p. 2042 – 2045;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia