Day: June 4, 2021

Synthetic Route of 1780-33-2, 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. 1780-33-2, name is 4,6-Dichloro-2,5-dimethylpyrimidine, molecular formula is C6H6Cl2N2, 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 C 4-Chloro-2,5-dimethyl-6-(2,4,6-trimethylphenoxy)-pyrimidine A solution of 2,4,6-trimethylphenol (2.720 g, 20 mmol) in 60 ml of dry THF was treated with NaH (60percent in oil, 1,200 g, 30 mmol) at room temperature. After stirring at room temperature for 15 minutes, 2,5-dimethyl-4,6-dichloropyrimidine (3.34 g, 20 mmol) was added and the resulting mixture was heated at reflux for 15 hours. The mixture was quenched with saturated ammonium chloride and extracted with ethyl acetate. The organic layer was dried and concentrated to give 5.4528 g of beige solid. The solid was recrystallized from isopropanol to give 5.1345 g of pale yellow solid. mp 86-87° C.; high MS (C15H17ClN20) calc. 276.1025, found 276.10359. 1H NMR (CDCl3) delta 6.87 (s, 2H), 2.37 (s, 6H), 2.28 (s, 3H), 2.01 (s, 6H) ppm.

According to the analysis of related databases, 1780-33-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc.; US6956047; (2005); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 13223-25-1, 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 13223-25-1 as follows.

Step 2: To an ice-cooled solution of 2-(4-nitro-1 H-pyrazol-1-yl)ethanol (1.90 g, 12.02 mmol) in THF (60 mL), NaH (673 mg, 16.82 mmol, 60 %) was added and the solution was stirred for 5 min at 0 C, then the ice bath was removed and the reaction mixture was stirred at rt for 30 min, before 2-chloro-4,6-dimethoxypyrimidine (2.31 g, 13.22 mmol) was added. After 40 min at rt, the reaction mixture was quenched with water and the org. solvent was removed in vacuo. The aq. layer was extracted with DCM (1 x), then acidified with 1 N HCI-solution to pH 2, and extracted with DCM (2x). The combined org. layers were washed with brine, dried (MgS04), filtered and the solvent removed under reduced pressure. Purification by crystallization (DCM-hept-mixture) yielded 4,6-dimethoxy-2-(2-(4-nitro-1 /-/-pyrazol-1- yl)ethoxy)pyrimidine as a beige solid. LC-MS conditions A: tR = 0.88 min, [M+H]+= 295.98.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13223-25-1, its application will become more common.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; BOLLI, Martin; BOSS, Christoph; BROTSCHI, Christine; GUDE, Markus; HEIDMANN, Bibia; SIFFERLEN, Thierry; WILLIAMS, Jodi, T.; WO2012/110986; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 7226-23-5 , The common heterocyclic compound, 7226-23-5, name is 1,3-Dimethyltetrahydropyrimidin-2(1H)-one, molecular formula is C6H12N2O, 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.

A solution of diisopropylamine (29.2 mL, 0.21 mol) in dry tetrahydrofuran (186 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (62 mL) was cooled to -78 C. and then treated with a 2.5M solution of n-butyllithium in hexanes (83.4 mL, 0.21 mol). The yellow-orange reaction mixture was stirred at -78 C. for 35 min and then slowly treated with a solution of 4-(methanesulfonyl)phenyl acetic acid methyl ester (45.35 g, 0.20 mol) in dry tetrahydrofuran (186 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (62 mL). The reaction mixture turned dark in color. The reaction mixture was then stirred at -78 C. for 50 min, at which time, a solution of iodomethylcyclopentane (50.08 g, 0.24 mol) in a small amount of dry tetrahydrofuran was added slowly. The reaction mixture was then stirred at -78 C. for 50 min, and then allowed to warm to 25 C. where it was stirred for 36 h. The reaction mixture was quenched with water (100 mL), and the resulting reaction mixture was concentrated in vacuo to remove tetrahydrofuran. The remaining residue was diluted with ethyl acetate (1.5 L). The organic phase was washed with a saturated aqueous sodium chloride solution (1*500 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 3/1 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-methanesulfonylphenyl)propionic acid methyl ester (41.79 g, 68%) as a yellow viscous oil: EI-HRMS m/e calcd for C16H22O4S (M+) 310.1239, found 310.1230.

The synthetic route of 7226-23-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffman-La Roche Inc.; US6610846; (2003); B1;,
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. 274693-26-4, name is 2-(((3aR,4S,6R,6aS)-6-(7-(((1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanol. This compound has unique chemical properties. The synthetic route is as follows. Safety of 2-(((3aR,4S,6R,6aS)-6-(7-(((1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanol

The intermediate TG-3 obtained in the step S3 is added to the reactor, and then dissolved in methanol, and the temperature is lowered to 2 C, and nitrogen gas is added thereto, and the methanol solution of hydrochloric acid is added dropwise under the temperature control for 2 hours. Water and ethyl acetate were added, the system was temperature-controlled at 15 C, and the liquid phase was separated. The aqueous phase was extracted twice with 5 times TG-3 weight of ethyl acetate. The organic phase was washed once with saturated aqueous sodium hydrogencarbonate and the organic layer was evaporated to dryness. After adding ethyl acetate, stirring to complete dissolution, heating to reflux, adding n-hexane dropwise, stirring and cooling to 22 C, stirring was continued for 1.5 h, filtration, and vacuum drying to obtain white solid TG-4 as a crude product; The mass ratio of TG-3, methanol, methanolic hydrochloric acid solution, water, ethyl acetate and n-hexane was 1:2.5:2.5:3:2:4.

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, 274693-26-4, 2-(((3aR,4S,6R,6aS)-6-(7-(((1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanol.

Reference:
Patent; Jiangxi Sinopharm Co., Ltd.; Yang Jianguo; Wan Yibin; Ge Youqun; Zuo Feihong; Yu Chengxiang; Yang Ming; Li Jinjin; Yu Lianxin; Liu Wei; Xie Liangliang; Liu Linhua; (19 pag.)CN108892670; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 14080-50-3, name is Thieno[2,3-d]pyrimidin-4(3H)-one, molecular formula is C6H4N2OS, 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. Safety of Thieno[2,3-d]pyrimidin-4(3H)-one

A solution of intermediate b (5.102 g, 0.033 mol) was added to toluene (100 mL) and its phosphorus oxychloride (30 ml) 90 C for 2 hours. The reaction solution was cooled and then added dropwise to ice water, The filter cake was dried to give a yellow powder of 2.432 g in a yield of 43.4%.

With the rapid development of chemical substances, we look forward to future research findings about 14080-50-3.

Reference:
Patent; Jiangxi Science and Technology Normal University; Zhu Wufu; Zheng Pengwu; Wang Linxiao; Lan Zhou; Tang Qidong; Liu Xiaobo; Wang Caolin; Zhao Bingbing; (30 pag.)CN107253964; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 4994-86-9 , The common heterocyclic compound, 4994-86-9, name is 4-Chloro-2-methylpyrimidine, molecular formula is C5H5ClN2, 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.

Pd(Ph3P)4 (37.7 mg, 0.033 mmol) was added to a mixture of 4-chloro-2-methylpyrimidine (117 mg, 0.913 mmol), 3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-6-methyl-2-pyridinecarbonitrile D67 (150 mg), copper(I) iodide (22.35 mg, 0.117 mmol) and cesium fluoride (198 mg, 1.304 mmol) in 1,4-dioxane (3 ml) at room temperature. The mixture was degassed via 3 vacuum/nitrogen cycles and sonicated briefly to homogenise the reaction mixture which was then heated to 65 C. with shaking for 1 hour. The mixture was cooled and filtered washing with EtOAc. The organic phase was evaporated under reduced pressure. The residue was taken up in EtOAc (30 ml) and washed with NaHCO3 solution, dried (Na2SO4) and evaporated under reduced pressure. This residue was purified twice by flash chromatography on silica gel (Biotage Snap 25 g column, EtOAc/Cy from 50/50 to 100/0 then Biotage Snap 25 g column, isocratic Et2O) to give 85 mg of almost pure title compound. This material was purified further by recrystallisation from EtOH/Cy to give the title compound D80 (59 mg) as a yellow solid.UPLC (Acid QC_POS-50-800): rt=0.53 minutes, peak observed: 211 (M+1). C12H10N4 requires 210. 1H NMR (400 MHz, CDCl3) delta ppm 2.72 (s, 3H) 2.87 (s, 3H) 7.55 (d, 1H) 7.75 (d, 1H) 8.24 (d, 1H) 8.85 (d, 1H).

The synthetic route of 4994-86-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALVARO, Giuseppe; Amantini, David; Castiglioni, Emiliano; Di Fabio, Romano; Pavone, Francesca; US2010/144760; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature 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.

Preparation of methyl (+/-)-2-(4,6-dimethoxy-2-pyrimidinyloxy)-3,3-dimethylbutanoate 4.38 g (25 mmol) of 2-chloro-4,6-dimethoxypyrimidine, 3.90 g (25 mmol) of methyl (+/-)-2-hydroxy-3,3-dimethylbutanoate and 0.66 g (6.3 mmol) of sodium methanesulfinate were heated in the presence of 5.17 g (37.5 mmol) of potassium carbonate in 25 ml of N,N-dimethylformamide to 120 C. with stirring. After 2 hours, the solvent was removed in a rotary evaporator at 70 C./20 mbar. The residue was taken up in 30 ml of water and 30 ml of dichloromethane. After the organic phase had been separated off, the aqueous phase was again extracted with 20 ml of dichloromethane. The combined organic phases was washed with water, dried over magnesium sulfate and evaporated. The title product was obtained in a yield of 5.93 g (82.7 percent of theory) in the form of pale yellowish crystals (GC content 99.2 percent). The melting point of the title compound was 104.4 to 107.0 C.

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; Lonza AG; US5840892; (1998); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 4595-60-2, 2-Bromopyrimidine, 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, HPLC of Formula: C4H3BrN2, blongs to pyrimidines compound. HPLC of Formula: C4H3BrN2

Preparation 21 4-Pyrimidin-2-yl-benzaldehyde A solution of 2-bromopyrimidine (1.00 g, 6.3 mmol) and tetrakistriphenylphosphine(0) palladium (0.218 g, 0.189 mmol) in ethylene glycol dimethyl ether (30 mL) was stirred at room temperature for 10 minutes. A solution of 4-formylbenzene boronic acid (1.14 g, 7.61 mmol) and sodium bicarbonate (1.58 g, 18.9 mmol) in 15 mL water was added and the reaction was heated at reflux for 16 h. The mixture was diluted with water and CH2Cl2. The layers were separated, and the aqueous solution was washed with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified via flash chromatography on silica gel (10% to 30% hexanes in EtOAc) to afford the title compound (0.979 g). 1H NMR (400 MHz, CDCl3) delta 10.11 (s, 1H), 8.83 (s, 2H), 8.82 (s, 1H), 7.98 (s, 2H), 7.23 (s, 2H).

The synthetic route of 4595-60-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US2005/203086; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 1780-26-3, name is 2-Methyl-4,6-dichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 1780-26-3

4,6-Dichloro-2-methyl-pyrimidine (5.0 g, 30.6 mmol) was added to a mixture of Isopropanol / NH3.H20 (40 mL / 10 mL). The reaction mixture was heated to 90 C for 18 h. After cooled to RT, the precipitate was collected by filtration, washed with H20 (10 mL x 3) and dried. 6-Chloro-2-methyl-pyrimidin-4-ylamine (1.5 g, yield: 33.9%) was obtained as a white solid.

With the rapid development of chemical substances, we look forward to future research findings about 1780-26-3.

Reference:
Patent; MANNKIND CORPORATION; TOLERO PHARMACEUTICALS, INC.; ZENG, Qingping; FARIS, Mary; MOLLARD, Alexis; WARNER, Steven L.; FLYNN, Gary A.; WO2014/52365; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
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. 1224944-77-7, name is Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate. A new synthetic method of this compound is introduced below., Recommanded Product: 1224944-77-7

To a solution of (tf)-2-(l-aminoethyl)-4-fluorophenol (2) (85 g, 443.56 mmol, 1.00 eq.) and ethyl 5-chloropyrazolo[l,5-a]pyrimidine-3-carboxylate (la) (100.08 g, 443.56 mmol, 1.00 eq.) in n-BuOH (2 L) was added DIEA (343.96 g, 2.66 mol, 6.00 eq.). The mixture was stirred at 120 C for 2 hrs. TLC (PE:EtOAc=l : l) showed the reaction was completed. The reaction mixture was diluted with H20 (500 mL) at 16 C, and extracted with EtOAc (500 mLx3). The combined organic layers were washed with brine (500 mL), dried over Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (Si02, Petroleum ether/Ethyl acetate=10/l to 1 :3) to give ethyl (K)-5-((l-(5- fluoro-2-hydroxyphenyl)ethyl)amino)pyrazolo[l,5-a]pyrimidine-3-carboxylate (3) (122 g, 349.34 mmol, 78.76% yield, ee>99% purity) as a white solid. 1HNMR (CDC13 , 400MHz) delta 9.28 (br. s., IH), 8.26 (s, IH), 8.14 (d, 7=7.5 Hz, IH), 6.95 – 6.89 (m, 2H), 6.87 – 6.80 (m, IH), 6.18 (d, 7=7.5 Hz, IH), 5.98 (d, 7=8.3 Hz, IH), 5.71 – 5.54 (m, IH), 4.50 – 4.35 (m, 2H), 1.60 (d, 7=6.8 Hz, 3H), 1.42 (t, J=7.2 Hz, 3H).

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, 1224944-77-7, Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate.

Reference:
Patent; TP THERAPEUTICS, INC.; CUI, Jingrong Jean; LI, Yishan; ROGERS, Evan W.; ZHAI, Dayong; DENG, Wei; HUANG, Zhongdong; (120 pag.)WO2017/15367; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia