Tag: M.W:100-200

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. 22536-61-4, name is 2-Chloro-5-methylpyrimidine, molecular formula is C5H5ClN2, 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. category: pyrimidines

In a sealed glass tube a suspension of l-cyclopropyl-6-(lH-imidazol-5-yl)-3,3-dimethylindolin- 2-one (example 71a, 70 mg), 2-chloro-5-methylpyrimidine (37.0 mg) and cesium carbonate (158 mg) in acetonitrile (1.05 ml) was heated to 120 C for 30 minutes under microwave irradiation. Then again 18 mg 2-chloro-5-methylpyrimidine and 89 mg cesium carbonate were added and the reaction mixture heated to 120C under conventional heating for 2 hours. The reaction mixture was concentrated in vacuo and purified by flash chromatography (silica gel, gradient, 0% to 100% EtOAc in n-heptane). The title compound was obtained as off white solid (75 mg, 80%). MS (ESI, m/z): 360.2 [(M+H)+].

With the rapid development of chemical substances, we look forward to future research findings about 22536-61-4.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HILPERT, Hans; KOLCZEWSKI, Sabine; LIMBERG, Anja; STOLL, Theodor; WO2015/177110; (2015); A1;,
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. 6153-44-2, name is Methyl 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate, molecular formula is C6H6N2O4, 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 Methyl 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate

6-morpholin-4-yl-2-pyridin-2-yl-pyrimidine-4-carboxyIic acidMethyl orotate (5 g, 29.41 mmol) was suspended in phosphorous oxychloride (50 ml) and the mixture was heated to reflux for 4 hours. After this time excess phosphorous oxychloride was removed under reduced pressure. The resulting dark residue was poured onto ice with vigorous stirring and the solution was left to stir until all the ice had melted. The crude product was then collected by filtration and the filtrate was extracted with ether (x2). The filtered product was added to the ether washings and dried over magnesium sulfate. The solution was then concentrated to give methyl 2,6-dichloropyrimidine-4- carboxylate (5.25g, 25.37mmol) as a yellow oil that solidified on standing. To this was added morpholine (2.005g, 25.37 mmol) and THF (40ml) and the mixture left for 2 hours at room temperature. The reaction was then evaporated to dryness to afford methyl 2- chloiO-6-morpholin-4-yl-pyrirnidine-4-carboxylate (5.4 Ig, 21 mmol) LCMS Spectrum: MH+ 258.39, Retention time 1.56, Method: Monitor Base Methyl 2-chloro-6-morpholin-4-yl-pyrimidine-4-carboxylate (2.58g, lOmmol), 2- tributylstannyl pyridine (4.055g, 11 mmol) and tetrakis(triphenylphosphine)palladium (0) (1 Omolpercent, lmmol, 1.116g) were suspended in THF (20 ml) and heated to 100 0C for 30 minutes in the microwave. To this mixture was added sodium hydroxide (20 ml) (4M in H2O), and the reaction was stirred for 1 hour. The resulting precipitate was collected by filtration found to be the monosodium salt of 6-morpholin-4-yl-2-pyridin-2-yl-pyrimidine- 4-carboxylic acid, (1.53g). LCMS Spectrum: (M+Na)+ 308.47, Retention Time 1.42, Method: Monitor BaseNMR Spectrum: 1H NMR (300.132 MHz, D2O) 53.70 – 3.86 (m, 8H), 7.11 (s, IH), 7.51 (ddd, IH), 7.94 (td, IH), 8.28 (d, IH), 8.60 (d, IH) ppm.

With the rapid development of chemical substances, we look forward to future research findings about 6153-44-2.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/80382; (2007); 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 1683-75-6, name is 2-Amino-4-chloro-5-fluoropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 2-Amino-4-chloro-5-fluoropyrimidine

To a solution of 6-bromo-4-methoxy-lH-indole-3-carbaldehyde A.140 (0.65 g, 2.56 mmol) in DMF (13 mL) at room temperature was added Cs2CO3 (2.50 g, 7.67 mmol) followed by 4-chloro-5-fluoropyrimidin-2-amine A.53 (0.453 g, 3.07 mmol) and the mixture was stirred at 80 0C for 6 hours. The mixture was concentrated under reduced pressure and purified by silica gel column chromatography using 0% to 100% gradient of dichloromethane-methanol- NH4OH (89:9:1) in dichloromethane as eluent to give l-(2-amino-5-fiuoropyrimidin-4-yl)-6- bromo-4-methoxy-lH-indole-3-carbaldehyde A.141 (0.319 g, 34.2% yield) as a yellow solid: 1H NMR (500 MHz, DMSO-d6) 5 ppm 10.39 (1 H, s), 8.56 (1 H, d, J=3.7 Hz), 8.32 (1 H, d, J=2.7 Hz), 7.95 (1 H, s), 7.13 (2 H, s), 7.12 (1 H, d, J=1.4 Hz), 4.01 (3 H, s); Mass Spectrum(ESI) m/e = 365.0 [M+l ( 79Br] and 367.0 [M+l (81Br)].

With the rapid development of chemical substances, we look forward to future research findings about 1683-75-6.

Reference:
Patent; AMGEN INC.; WO2009/158011; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 3435-25-4, 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 3435-25-4, name is 4-Chloro-6-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Example 8: Synthesis of (S)-methyl-2-((2R,3R)-3-((S)-1 -((3R,4S,5S)-4-((S)-N,3-dimethyl- 2-((4-methylpyrimidin-2-yl)amino)butanamido)-3-methoxy-5-methylheptanoyl)pyrrolidin-2- yl)-3-methoxy-2-methylpropanamido)-3-phenylpropanoate (FP-8)To a solution of Val-Dil-Dap-PheOMe TFA salt (5.0 mg, 0.0067 mmol) in 2-propanol (2 ml) in a 4 oz. vial were added 2-chloro-4-methylpyrimidine (2.6 mg, 0.020 mmol) and DIEA (4.3 mg, 0.033 mmol). The vial was sealed and heated at 100 oC for 4 days. The crude was purified by preparative HPLC using a 20-50% gradient to obtain (S)-methyl-2- ((2R,3R)-3-((S)-1 -((3R,4S,5S)-4-((S)-N,3-dimethyl-2-((4-methylpyrimidin-2- yl)amino)butanamido)-3-methoxy-5-methylheptanoyl)pyrrolidin-2-yl)-3-methoxy-2- methylpropanamido)-3-phenylpropanoate (FP-8) as a TFA salt

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 3435-25-4, 4-Chloro-6-methylpyrimidine.

Reference:
Patent; NOVARTIS AG; GEIERSTANGER, Bernhard; GRUNEWALD, Jan; OU, Weijia; PAN, Shifeng; UNO, Tetsuo; WAN, Yongqin; WANG, Xing; WO2015/189791; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 49844-90-8, Adding some certain compound to certain chemical reactions, such as: 49844-90-8, name is 4-Chloro-2-(methylthio)pyrimidine,molecular formula is C5H5ClN2S, 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 49844-90-8.

4-Chloro-2-methylthiopyrimidine (9 g, 56.0 mmol) was added to 47% HI (55 mL) solution and the mixture was stirred at room temperature for 48 hours. The precipitated solids were filtered, dissolved in water (100 mL) and added 20% NaOH to adjust pH 8. The mixture was extracted with chloroform and the extract was washed with water and dried over MgSO4 and, subsequently, the solvent was evaporated. The residue was recrystallized from petroleum ether to give the title compound (9.5 g, 36.7 mmol, yield 67%).1H-NMR (CDCl3) delta: 2.54 (s, 3H), 7.41 (d, IH), 8.01 (d, IH)

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. 49844-90-8, 4-Chloro-2-(methylthio)pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DONGBU HANNONG CHEMICALS CO., LTD.; WO2006/137658; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 39906-04-2, 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.39906-04-2, name is 4,6-Dichloro-2-methylpyrimidin-5-amine, molecular formula is C5H5Cl2N3, molecular weight is 178.02, as common compound, the synthetic route is as follows.

Example 77 (1 S,2R)-2-(4-(diisobutylamino)-3-(3-(2-methylpyrimidin-5-yl)ureido)phenyl)cyclopropanecarboxylic acid 77A. 2-methylpyrimidine-5-amineA solution of 4,6-dichloro-2-methylpyrimidin-5-amine (2 g, 11.23 mmol) in ethylether (93 ml) was treated with sodium hydroxide (7.37 g, 184 mmol) in water (22.05 ml)and 10% palladium on carbon (0.161 g, 1.5 17 mmol). The mixture was shaken at rt on aParr shaker under 50 psi of H2 gas for 22 h. The reaction was filtered through Celite andthe filter cake was washed with DCM. The solvent from the filtrate was evaporated togive a yellow residue. The suspension was re-dissolved in DCM and water. The aqueous layer was neutralized to approximately pH 6 with 4N HC1, then extracted with DCM (3X). The combined organic phases were dried over anhydrous Na2SO4, filtered, and concentrated to afford a yellow residue. The aqueous phase still contained product, so thewater was evaporated to give a yellow solid. The solid was taken up in MeOH and DCM and filtered to remove all salts. The filtrate was evaporated to give a yellow residue. A total of two crops were obtained – one from the extraction and one from the aqueous layer. Each crop was purified by flash chromatography and combined to give 77A (off- white solid, 0.968 g, 8.87 mmol, 79 % yield). ?H NMR (400MHz, CHLOROFORM-d) oe8.14 (s, 2H), 3.60 (br. s., 2H), 2.61 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 39906-04-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; HUANG, Audris; CHEN, Bin; CHEN, Libing; SEITZ, Steven P.; HART, Amy C.; MARKWALDER, Jay A.; WO2014/150677; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1820-81-1, Adding some certain compound to certain chemical reactions, such as: 1820-81-1, name is 5-Chlorouracil,molecular formula is C4H3ClN2O2, 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 1820-81-1.

5-Chlorouracil (4.5 g, 30.82 mmol) was dissolved in phosphorus oxychloride (100 mL) and phosphorus pentachloride (19.2 g, 92.46 mmol) was added. The reaction mixture was heated at reflux overnight; it was then cooled to RT and the solvent was evaporated under reduced pressure. The residue was cooled to 0 0C and ice flakes were carefully added. The resulting mixture was stirred for 10 minutes; it was then partitioned between water and DCM. The organic phase was separated and washed 3 times with water. The aqueous layers were combined and extracted twice with DCM. The combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure to give f> o fQS% vipid) of 2,4, 5-trichloro-pyrimidine as a yellow oil without further purifications.

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. 1820-81-1, 5-Chlorouracil, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2008/28860; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference 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.

EXAMPLE 29 3-Cyclopentyl-N-pyridin-2-yl-2-(4-pyridin-4-yl-phenyl)-propionamide A solution of diisopropylamine (17.1 mL, 122.21 mmol) in dry tetrahydrofuran (55 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (18 mL) was cooled to -78 C. under nitrogen and then treated with a 10M solution of n-butyllithium in hexanes (12.2 mL, 122.21 mmol). The yellow reaction mixture was stirred at -78 C. for 30 min and then treated dropwise with a solution of 4-iodophenylacetic acid (15.25 g, 58.19 mmol) in dry tetrahydrofuran (55 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (18 mL). The reaction mixture turned dark in color and was allowed to stir at -78 C. for 45 min, at which time, a solution of iodomethylcyclopentane (13.45 g, 64.02 mmol) in a small amount of dry tetrahydrofuran was added dropwise. The reaction mixture was allowed to warm to 25 C. where it was stirred for 42 h. The reaction mixture was concentrated in vacuo to remove tetrahydrofuran and then quenched with a 10% aqueous hydrochloric acid solution (100 mL). The resulting aqueous layer was extracted with ethyl acetate (3*200 mL). The combined organic extracts were washed with a saturated aqueous sodium chloride solution (1*200 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-iodo-phenyl)-propionic acid (13.97 g, 70%) as a cream solid: mp 121-122 C.; EI-HRMS m/e calcd for C14H17IO2 (M+) 344.0273, found 344.0275.

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

Reference:
Patent; Corbett, Wendy L.; Haynes, Nancy-Ellen; Sarabu, Ramakanth; US2002/2190; (2002); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 873-83-6 ,Some common heterocyclic compound, 873-83-6, molecular formula is C4H5N3O2, 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 2-hydroxynaphthalene-1,4-dione (0.17 g, 1 mmol), 4-chlorobezaldehyde(0.14 g, 1 mmol), 6-amino-uracil (0.12 g, 1 mmol), and p-TSA (0.05 g) in refluxing water (5 mL) was stirred for 6 h. After completion of the reaction as confirmed by thin-layer chromatography (TLC) (eluent EtOAc=n-hexane, 1:3), the reaction mixture was cooled to room temperature. The precipitated product was separated by filtration, washed three times with water and 5mL acetone, and dried at 60?70 ¡ãC. Corresponding products were analytically pure without recrystallization.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,873-83-6, its application will become more common.

Reference:
Article; Azizian, Javad; Delbari, Akram Sadat; Yadollahzadeh, Khadijeh; Synthetic Communications; vol. 44; 22; (2014); p. 3277 – 3286;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 42754-96-1, 4,6-Dichloro-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, Application In Synthesis of 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine, blongs to pyrimidines compound. Application In Synthesis of 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine

TMSOTf (1.04 g, 4.72 mmol) and DBU (532 mg, 3.54 mmol) were added to a solution of 5b (520 mg, 1.18 mmol) and 4,6-dichloro-1H-pyrazolo[3,4-djpyrimidine (220 mg, 1.18 mmol) in MeCN (14 mL) successively. After the reaction mixture was stirred at rt for 2 h, it was poured into sat.aq. NaHCO3 and extracted with EtOAc. The organic layer was washed with brine, dried and concentrated in vacuo. The residue was purified by column chromatography (Si02, 33% EtOAc petroleum ether) to afford the title compound (5c) (250 mg, 38% yield) as a mixture of two diastereomers.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,42754-96-1, 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ORIC PHARMACEUTICALS, INC.; DU, Xiaohui; EKSTEROWICZ, John; FANTIN, Valeria R.; JACKSON, Erica L.; SUN, Daqing; YE, Qiuping; MOORE, Jared; ZAVOROTINSKAYA, Tatiana; (262 pag.)WO2019/90111; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia