Tag: M.W:200-300

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. 1780-40-1, name is 2,4,5,6-Tetrachloropyrimidine, molecular formula is C4Cl4N2, 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. Quality Control of 2,4,5,6-Tetrachloropyrimidine

A hydroxyl group-containing tertiary amine betaine was prepared according to the method of Example 1.The tertiary amine betaine was dissolved in 500 mL of deionized water and added to a round bottom flask with mechanical stirring,Cool to about 10 C.108.5g of 2,4,5,6-tetrachloropyrimidine fine powder was added under stirring, and after stirring well,A solution of 26 g of sodium carbonate dissolved in 50 mL of deionized water was added portion wise with stirring.After adding continue to react 3 ~ 5h.Then slowly add potassium acetate to the reaction solution to precipitate the product, after filtration and washed with anhydrous ethanol,Vacuum drying to obtain a trichloropyrimidine active group tertiary amine betaine antibacterial agent.

With the rapid development of chemical substances, we look forward to future research findings about 1780-40-1.

Reference:
Patent; Hong Kong Polytechnic University; Xin Haozhong; He Liang; Gao Chang; (17 pag.)CN106928158; (2017); A;,
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 130049-82-0, name is 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C11H15ClN2O2

Step A 9-((tert-butyldimethylsilyl)oxy)-3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one A solution of 3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one (1.0 g, 4.12 mmol) in DMF (5 mL) was treated with 1H-imidazole (701.24 mg, 64.66 mmol), followed by a solution of t-butyldimethylchlorosilane (683.12 mg, 4.53 mmol) in DMF (1 mL). After stirring for 18 h at room temperature, the solvents were removed under vacuum and the residue was taken up in dichloromethane/water (10 mL/10 mL) with addition of a spatula of potassium carbonate. The aqueous layer was extracted with dichloromethane (three times 10 mL). The combined organic fractions were dried over Na2SO4, filtered, and the solvent was removed under vacuum. The crude mixture was used without further purification in the next step. (ESI-MS (M+1) 357).

With the rapid development of chemical substances, we look forward to future research findings about 130049-82-0.

Reference:
Patent; Hryhorenko, Eric; Sankaran, Banumathi; DeCory, Thomas R.; Tubbs, Theresa; Colt, Linda; Vliegen, Maarten; Haspeslagh, Pieter Rik; US2014/57301; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 35265-82-8, 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 35265-82-8, name is 2,4-Dichloro-6-methylthieno[3,2-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

At normal temperature a solution of bromine (1.44 mE, 27.6 mmol) in acetic acid (10 mE) was slowly added dropwise into a solution of 8-g (prepared according to the method ofpatent: W02007/023382A2)(1.984 g, 9.2mmol) and aluminum trichloride (2.46 g, 18.4 mmol) in acetic acid (30 mE). The mixture was heated to 80 C. to react for 6 irs afier the addition was completed. The reaction mixture was cooled, and then partitioned between ethyl acetate (80 mE) and water (80 mE). The organic layer was separated and washed with 5% sodium thiosulfate solution (2×80 mE). The aqueous phase was extracted with ethyl acetate (x2), the combined organic phase was washed sequentially with saturated sodium bicarbonate solution (200 mE) and saturatedbrine (400 mE), dried over anhydrous sodium sulfate, and concentrated under reduced pressure, to yield target compound 8-f(1 .035 g, yield 76%) as a pale yellow solid. EC-MS (ESI): mlz 296.9 (M+H).

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 35265-82-8, 2,4-Dichloro-6-methylthieno[3,2-d]pyrimidine.

Reference:
Patent; SHANGHAI YINGLI PHARMACEUTICAL CO., LTD; XU, Zusheng; (174 pag.)US2016/214994; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 6693-08-9, 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 6693-08-9, name is 2,4,6-Trichloro-5-fluoropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 3-amino-5-isoproxypyrazole (1.75 g, 12.41 mmol) in THF (20 ml) was added triethylamine (1.51 g, 14.89 mmol) and then slowly a solution of 2,4,6-trichloro-5- fluoropyrimidine (WO200549033, 2.50 g, 12.41 mmol) in THF (20 ml) at 0 0C. The resulting mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue was diluted with EtOAc. The solution was then washed with brine twice. The organic layer was obtained and evaporated to dryness. The dried residue was subject to silica gel chromatographic purification (by ISCO Combiflash with gradient EtOAc/hexanes) to afford EPO the desired product (1.40 g, yield 79%). LC-MS, 264 (M-41); 1H NMR (CDCl3) delta 8.70 (s, IH), 5.90 (s, IH), 4.50 (m, IH), 1.22 (d, 6H).

According to the analysis of related databases, 6693-08-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/123113; (2006); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 90914-41-3, 3-Bromo-4-chloro-1H-pyrazolo[3,4-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, Quality Control of 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine, blongs to pyrimidines compound. Quality Control of 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine

1-(1-benzyl-4-piperidinyl)-3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine (Intermediate C) 3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine (Intermediate B) (5.0 g, 21.42 mmol), 1-benzyl-4-piperidinol (8.2 g, 42.83 mmol) and triphenylphosphine (11.23 g, 42.83 mmol)were suspended in 250 ml of tetrahydrofuran. The reaction mixture was cooled in an ice-water bath and diethyl azodicarboxylate (6.8 ml, 42.83 mmol) was added dropwise. 10 minutes later, the reaction mixture was allowed to warm up to room temperature. After stirring for 2 hours, solvent was removed and the residue was taking into ethyl acetate. The organic layer was washed, dried and evaporated. The crude product was passed through Biotage flash column using dichloromethane/ethyl acetate (90:10) as the mobile phase to yield 10.56 g of 1-(1-benzyl-4-piperidinyl)-3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine. The product was 61% pure with a HPLC retention time of 12.46 min. (HPLC condition: 5 to 95% CH3CN in 0.1 N aqueous ammonium acetate over 20 min., the column size is 3.9*150 mm, 300 A).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,90914-41-3, 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Abbott Laboratories; US2002/156081; (2002); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 63558-65-6, name is 4-Chloro-5-iodopyrimidine, the common compound, a new synthetic route is introduced below. Recommanded Product: 4-Chloro-5-iodopyrimidine

Step 3: N-4′-[(5-Iodopyrimidin-4-yl)amino]-6-methylbiphenyl-3-yl-3-(trifluoromethyl)benzamideTo lambda^-(4′-amino-6-methylbiphenyl-3-yl)-3-(trifluoromethyl)benzamide (60.0 mg, 0.162 mmol) was added 4-chloro-5-iodopyrimidine (39 mg, 0.16 mmol) followed by ethanol (0.47 mL). The reaction was heated to 80 0C in a sealed tube until LCMS indicated complete reaction, typically 1 -2 hours. The reaction was cooled to ambient temperature and the solvent was evaporated. The residue was partitioned between saturated aqueous NaHCO3 and EtOAc, the organic phase was washed with brine, dried (MgSO4) and evaporated to leave the crude product, which was then purified by column chromatography to give the final compound (39.9 mg, 42.88%). 1H NMR (400 MHz, CDCl3): delta 8.61 (s, 2H), 8.14 (s, IH), 8.08 (d, IH), 7.95 (s, IH), 7.81 (d, IH), 7.5-7.7 (m, 5H), 7.40 (m, 3H), 7.29 (d, IH), 2.29 (s, 3H). MS (EI) m/z = 575 (M+H).

The synthetic route of 63558-65-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INCYTE CORPORATION; WO2008/79965; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 583878-42-6, Adding some certain compound to certain chemical reactions, such as: 583878-42-6, name is Ethyl 4-chloro-6-methyl-2-(methylthio)pyrimidine-5-carboxylate,molecular formula is C9H11ClN2O2S, 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 583878-42-6.

To a solution of Intermediate III-A1 (400 mg, 1 mmol) dissolved in MeOH (4 mL) was added conc. HCl (4 mL) . The resulting mixture was concentrated at 50 to dryness. The residue was dissolved in n-BuOH (20 mL) , and then added DIEA (1 mL) and ethyl 4-chloro-6-methyl-2- (methylthio) pyrimidine-5-carboxylate (246 mg, 1 mmol) . The mixture was stirred at rt. for 2h, and then concentrated to remove the solvent. The residue was purified by flash column chromatography to afford the title compound as a solid (500 mg) . Yield: 97.8. MS (ESI) : calcd. value for C24H23ClN6O3S is 510.12, m/z measured value is 511.1 (M+1)+.

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. 583878-42-6, Ethyl 4-chloro-6-methyl-2-(methylthio)pyrimidine-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-Guo; DAI, Guangxiu; JIA, Hong; ZHANG, Zhulin; WENG, Jianyang; VENABLE, Jennifer Diane; BEMBENEK, Scott Damian; CHAI, Wenying; MEDUNA, Steven Paul; KEITH, John Matthew; ECCLES, Wendy; LEBSACK, Alec Donald; JONES, William Moore; SMITH, Russell Christopher; (195 pag.)WO2016/119707; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 32779-37-6, 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.32779-37-6, name is 2,5-Dibromopyrimidine, molecular formula is C4H2Br2N2, molecular weight is 237.88, as common compound, the synthetic route is as follows.

5.4 A mixture of 1.06 g (5.85 mmol) trans-4-(4-Methylamino-cyclohexyl)-but-3-yn-1-ol, 1.67 g (7.02 mmol) of 2,5-dibromo-pyrimidine [Brown, Desmond J.; Arantz, B. W., Pyrimidine reactions. XXII. Relative reactivities of corresponding chloro-, bromo-, and iodopyrimidines in aminolysis. J. Chem. Soc. C (1971), Issue 10, 1889-91] and 3.38 ml (19.88 mmol) N-ethyldiisopropylamine were heated for 2 h at 85 C., diluted with 1 ml DMA and heated for 3.5 h at 85 C. The reaction was cooled, evaporated and partitioned between aqueous saturated NaHCO3/Et2O (3*). The organic phases were washed with aqueous 10% NaCl, dried (NaSO4) and evaporated. Flash chromatography on silica gel (hexane/EtOAc 9:1 to 1:1) gave 1.37 g (69%) of trans-4-{4-[(5-Bromo-pyrimidin-2-yl)-methyl-amino]-cyclohexyl}-but-3-yn-1-ol, MS: 338 (MH+, 1Br).

Statistics shows that 32779-37-6 is playing an increasingly important role. we look forward to future research findings about 2,5-Dibromopyrimidine.

Reference:
Patent; Ackermann, Jean; Aebi, Johannes; Dehmlow, Henrietta; Maerki, Hans-Peter; Morand, Olivier; US2003/186984; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 151266-23-8 , The common heterocyclic compound, 151266-23-8, name is 3-Iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine, molecular formula is C5H4IN5, 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 a suspension of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (103) (2.0 g, 7.66 mmol) in anhydrous N,N-dimethylformamide (50 mL) under an argon atmosphere, potassium carbonate (4.23 g, 30.6 mmol) and bromocyclopentane (1.37 g, 9.20 mmol, 1.2 eq) were added sequentially. The resulting mixture was stirred at 80 C. for 5 h and then was allowed to cool to room temperature. The mixture was filtered and the filtrate was concentrated to half volume in vacuo and then partitioned between water and ethyl acetate. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford the desired product, 1-cyclopentyl-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (601) (1.27 g, 50.4% yield) as a yellow solid. ESI-MS (M+H)+ m/z: 330.1.

The synthetic route of 151266-23-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Intellikine LLC; Ren, Pingda; Liu, Yi; Wilson, Troy Edward; Li, Liansheng; Chan, Katrina; US2015/225407; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 74901-69-2, 2,4-Dichloro-6,7-dihydrothieno[3,2-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, 74901-69-2, blongs to pyrimidines compound. Quality Control of 2,4-Dichloro-6,7-dihydrothieno[3,2-d]pyrimidine

To a solution of 2,4-dichloro-6,7-dihydrothieno[3,2-d]pyrimidine (2.50 g, 12 mmol) in DMSO (8 mL) was added DIPEA (4.2 mL, 24 mmol) and 6-oxaspiro[3.3]heptan-2- amine hydrochloride (2.00 g, 13 mmol) was added. The reaction mixture was stirred at rt overnight. Water ( 10 mL) was added and the obtained slurry was stirred for 30 min before filtration and subsequent washings with water afforded the title compound as solid material. 1H NMR (DMSO-d6) delta: 7.43 (d, J = 7.1 Hz, 1H), 4.62 (s, 2H), 4.49 (s, 2H), 4.26 (h, J = 8.1 Hz, 1H), 3.39 – 3.31 (m, 2H), 3.17 – 3.08 (m, 2H), 2.62 – 2.53 (m, 2H), 2.30 – 2.16 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,74901-69-2, its application will become more common.

Reference:
Patent; LEO PHARMA A/S; LARSEN, Jens; (110 pag.)WO2019/57806; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia