Tag: M.W:200-300

Application of 22276-95-5, 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. 22276-95-5, name is 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below.

To a mixture of 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (G-1) (6.24 g, 26.8 mmol, 1.0 eq) in anhydrous THF (100 mL) at -78 C. under argon, n-BuLi solution (2.5 M in THF, 23.6 mL, 59.0 mmol, 2.2 eq) is added dropwise over 30 min. The reaction mixture is stirred at -78 C. for 1 h and then dry ice (300 g) is added in portions under an argon atmosphere. The resulting mixture is allowed to warm to RT and then stirred at RT overnight. The reaction mixture is diluted with H2O (200 mL) and extracted with ethyl acetate (50 mL*4). The aqueous layer is acidified with conc. HCl to adjust the pH to 3-4. The precipitate is collected by filtration, rinsed with H2O (30 mL) and dried in vacuo to afford the product, 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid (H-1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22276-95-5, its application will become more common.

Reference:
Patent; Ren, Pingda; Liu, Yi; Li, Liansheng; Chan, Katrina; Wilson, Troy Edward; Castro, Alfredo C.; Evans, Catherine A.; Snyder, Daniel A.; US2012/122838; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 938443-20-0, 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.938443-20-0, name is 2,4,7-Trichloropyrido[2,3-d]pyrimidine, molecular formula is C7H2Cl3N3, molecular weight is 234.4699, as common compound, the synthetic route is as follows.

[00383] To a solution of 2,4,7-trichloropyrido[2,3-d]pyrimidine (4.0 g, 17.06 mmol, 1.0 equiv) in DMA (10 mL) was added (3,S)-3-methylmorpholine (4.31 g, 42.65 mmol, 2.5 equiv) and DIPEA (5.51 g, 42.65 mmol, 7.43 mL, 2.5 equiv). The reaction solution was heated to 70 C for 48 h. The reaction suspension was cooled to room temperature, poured into cold H2O (50 mL) to precipitate out a solid. The solid was filtered and the filter cake was rinsed with H2O, and dried under reduced pressure to give the crude product, which was purified by column chromatography on silica gel (0?100% petroleum ether/EtOAc) to give (3S)-4-[7- chloro-2-[(3,S)-3-methylmorpholin-4-yl]pyrido[2,3-d] pyrimidin-4-yl] 3-methyl-morpholine (3.5 g, 56.4% yield) as a yellow solid. LCMS (ESI) m/z: [M + H] calcd for C17H22CIN5O2: 364.15; found 364.2.

The chemical industry reduces the impact on the environment during synthesis 938443-20-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; REVOLUTION MEDICINES, INC.; SEMKO, Christopher; PITZEN, Jennifer; WANG, Gang; TIBREWAL, Nidhi; AGGEN, James Bradley; THOTTUMKARA, Arun P.; BURNETT, G. Leslie; GLIEDT, Micah James Evans; KISS, Gert; WON, Walter; LEE, Julie Chu-li; GILL, Adrian Liam; (538 pag.)WO2018/204416; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 108381-23-3 ,Some common heterocyclic compound, 108381-23-3, molecular formula is C9H11ClN2O2, 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 mixture of 2-amino-6-methoxy-l,2,3,4-tetrahydro-naphthalene hydrochloride (87mg, 0.43mmol), 2-chloro-4,6-dimethyl-pyrimidine-5-carboxylic acid ethyl ester (71mg, O.33mmol) and KOAc (150mg, 1.5mmol) in ethanol (3ml) was microwaved at 120 C for lh. The reaction mixture was cooled to rt, quenched with 1NHC1 and extracted with EtOAc. The organic layer was washed with brine, dried over Na2S04, filtered and concentrated. The crude residue was purified by flash chromatography with a 5-60% EtOAC in hexane gradient to afford the desired product (69mg, 60% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,108381-23-3, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GILLESPIE, Paul; MICHOUD, Christophe; RUPERT, Kenneth Carey; THAKKAR, Kshitij Chhabilbhai; YI, Lin; WO2012/123467; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 874676-81-0 ,Some common heterocyclic compound, 874676-81-0, molecular formula is C4H2ClIN2, 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.

[00201] Step 1 : 5-Chloro-2-iodopyrimidine (4 g, 16.64 mmol) and tetrakis(triphenylphosphine)palladium(0) (1.92 g, 1.66 mmol) were suspended in THF (83 mL). 3-Ethoxy-3-oxopropylzinc bromide (33.3 mL, 16.64 mmol) was added, and the resultant mixture was stirred at room temperature for 18 hours. The mixture was diluted with saturated ammonium chloride and water (1 : 1) and extracted with EtOAc (3×100 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (EtOAc:Hexanes) to give ethyl 3-(5-chloropyrimidin-2-yl)propanoate. MS ESI calcd for C9H12C1N202 [M + H]+ 215, found 215. ‘H NMR (500 MHz, DMSO-d6) delta 8.82 (s, 2H), 4.00 (q, J= 7.1 Hz, 2H), 3.13 (t, J = 6.9 Hz, 2H), 2.78 (t, J= 6.9 Hz, 2H), 1.1 1 (t, J = 7.1 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,874676-81-0, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HAIDLE, Andrew, M.; ALTMAN, Michael, D.; KATTAR, Solomon, D.; CHRISTOPHER, Matthew; ELLIS, John, Michael; FISCHER, Christian; NORTHRUP, Alan, B.; CHILDERS, Kaleen Konrad; WO2013/192088; (2013); 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 126728-20-9, name is 2,4-Dichloropyrido[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

General procedure: A mixture of 5 (5.0 mmol), the respective amine (12 mmol), equimolecular amounts of triethylamine, and ethanol (15 mL) was heated at 70 C for 5 h with stirring. The solvent was removed under vacuum and the residue was dissolved in water (30 mL); the mixture was extracted with chloroform (3 × 25 mL) and the organic extracts were dried over anhydrous sodium sulfate and the solvent was removed in vacuum. For compounds 6t-y the resulting solid was purified by recrystallization as indicated in Table 1. For compounds 6z-ai the residual material isolated after removal of the solvent was washed with 5% HCl (25 mL) and the resulting solid was isolated and purified as indicated in Table 1.

With the rapid development of chemical substances, we look forward to future research findings about 126728-20-9.

Reference:
Article; Font, Maria; Gonzalez, Alvaro; Palop, Juan Antonio; Sanmartin, Carmen; European Journal of Medicinal Chemistry; vol. 46; 9; (2011); p. 3887 – 3899;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 3177-20-6, Methyl 2,4-dichloropyrimidine-5-carboxylate, 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, SDS of cas: 3177-20-6, blongs to pyrimidines compound. SDS of cas: 3177-20-6

Alternatively, instead of the hydrazone linkage describe above, the compounds may have an amide linkage (see Scheme I below). The synthesis consists of 3 steps. First, to a stirred solution of 4-(2-hydroxyethyl)morpholine (B) (2.8 g, 21.3 mmol) in anhydrous THF (45 mL) at 0 0C, sodium hydride, 60percent dispersion in mineral oil, (0.9 g, 22.5 mmol) is added in three portions under nitrogen purge. Ice-bath was removed and a mixture is stirred at room temperature for 20-30 minutes. The mixture is cooled to 0 0C and added drop-wise (using syringe or dropping funnel) under nitrogen purge to a solution of methyl 2,4-dichloropyrirnidine carboxylate (A) (4.03 g, 19.4 mmol) in anhydrous THF (35 mL) at 0 0C. The resultant solution is stirred for 30 minutes at 0 0C, followed by 30 minutes at room temperature. It is then quenched carefully with ice-water (115mL) and diluted with ethyl acetate (115 mL). Organic layer is separated, water layer extracted once with ethyl acetate, combined ethyl acetate extracts are washed with brine and dried over anhydrous sodium sulfate. Concentration, followed by column chromatography with gradient eluation (hexane : ethyl acetate, 1:1; hexane : ethyl acetate,l:2; ethyl acetate; dichloromethane-acetone-methanol, 3:1:01) affords 3 fractions: first (0.56 g, 9.5percent ) – mostly isomer C, second (1.28 g, 21.8percent)- a mixture of C and D, and byproduct (E), third (0.7 g, 11.9percent) – mostly isomer (D). EPO In the second step, a solution of compound C (0.6 g, 2 mmol), 5-amino-2,3- dimethylindole (F) (0.32 g, 2 mmol) and DIPEA (0.28 g, 2.2 mmol)in dioxane is heated at reflux for two hours. Ethyl acetate and water are added to the concentrated reaction mixture, water layer extracted with ethyl acetate, combined ethyl acetate extracts washed with brine and dried over anhydrous sodium sulfate. Product G (0.64 g, 75percent) is isolated by column chromatography with gradient eluation (ethyl acetate; dichloromethane- acetone-methanol, 3:1:01).In the same manner compound D is converted into product H.Compounds H is then converted into their corresponding amides (I) using appropriate amines following general procedure for amide formation.To a stirred mixture of ester (1 mmol) and amine (1.05 mmol) in toluene (3.2 mL)., 2 M solution of trimethylaluminum in toluene (1.6 eq) is added drop-wise under nitrogen purge. The reaction mixture is stirred until gas evolution halted, and then mixture is micro waved at 120 0C for 5-7 minutes (Emrys Optimizer). To the reaction mixture were added IN NaOH solution and dichloromethane, organic layer separated, washed with water, brine and dried over anhydrous sodium sulfate. Flash column chromatography purification affords about 65-75percent of a desired amide (I).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3177-20-6, Methyl 2,4-dichloropyrimidine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; SYNTA PHARMACEUTICALS CORP.; WO2006/53109; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 145783-15-9, 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine, 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, Formula: C7H9Cl2N3S, blongs to pyrimidines compound. Formula: C7H9Cl2N3S

Example 6 Synthesis of 2-[((3aR,4S,6R,6aS)-6-[[5-amino-6-chloro-2-(propylthio)pyrimidin-4-yl]amino]-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy]ethanol (Compound I) Take 250mL reaction flask 4,6-dichloro-2-(propylthio)pyrimidin-5-amine (16.1g, 68mmol), 2-[[(3aR,4S,6R,6aS)-6-amino-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]-dioxol-4-yl]oxy]-1-ethanol (14.8g, 68mmol), triethylamine (68.7g, 680mmol) and n-butanol (100mL) were added at atmospheric pressure. The resulting reaction mixture was sealed and heated to 100C, reflux for 55h. Followed by cooling to 30C. The solvent was distilled off. Isopropyl acetate and water, the phases were separated. The aqueous phase was extracted with isopropyl acetate, the combined organic phases, washed. Dried over anhydrous magnesium sulfate. Filter. The solvent was distilled off, give a reddish brown oil. N-heptane was added after a beating, white solid 24.9g, yield 87.2%. HPLC purity was 99.4%.

The synthetic route of 145783-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Qingdao Huanghai Pharmaceutical Co., Ltd.; Zhang, Fuli; Xu, Jianguo; Liu, Xiaohua; Gao, Yongji; He, Xiaoqing; Xu, Taizhi; Hu, Jie; (12 pag.)CN103626745; (2016); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 10457-14-4 ,Some common heterocyclic compound, 10457-14-4, molecular formula is C10H20N2O2Si2, 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.

TMS-protected uracil was dissolved in dry MeCN (10 ml) under nitrogen and TMSOTf (7.12 g,32 mmol) was added dropwise. When the reaction mixture was added with stirring, the mixture was clarified and compound V (1 g, 4 mmol ) In MeCN (2 ml) wasadded dropwise to the above reaction mixture. The mixture was stirred at 40 C for 10 h. TLC Compound V was quenched with ice water, filtered through celite and washed withDCM (30 ml * 2 times) The filter cake was separated and the organic phase was washed with NaCl (sat), dried over anhydrous sodium sulfate and the crude product was spin-dried directlyfor the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10457-14-4, its application will become more common.

Reference:
Patent; Shanghai Hongbozhiyuan Pharmaceutical Co., Ltd.; Li Dafeng; Chen Ping; (15 pag.)CN107200757; (2017); 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. 126728-20-9, name is 2,4-Dichloropyrido[2,3-d]pyrimidine, molecular formula is C7H3Cl2N3, 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. SDS of cas: 126728-20-9

General procedure: A mixture of 5 (5.0 mmol), the respective amine (12 mmol), equimolecular amounts of triethylamine, and ethanol (15 mL) was heated at 70 C for 5 h with stirring. The solvent was removed under vacuum and the residue was dissolved in water (30 mL); the mixture was extracted with chloroform (3 × 25 mL) and the organic extracts were dried over anhydrous sodium sulfate and the solvent was removed in vacuum. For compounds 6t-y the resulting solid was purified by recrystallization as indicated in Table 1. For compounds 6z-ai the residual material isolated after removal of the solvent was washed with 5% HCl (25 mL) and the resulting solid was isolated and purified as indicated in Table 1.

With the rapid development of chemical substances, we look forward to future research findings about 126728-20-9.

Reference:
Article; Font, Maria; Gonzalez, Alvaro; Palop, Juan Antonio; Sanmartin, Carmen; European Journal of Medicinal Chemistry; vol. 46; 9; (2011); p. 3887 – 3899;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 56686-16-9, 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 56686-16-9 as follows.

t-BuLi (Aldrich; 1.7 M soln in pentane, 1.1 mL) was added to a mixture of 8 (Aldrich; 200 mg, 0.9 mmol) and dry THF (2 mL) at -78 C under argon. The mixture was left at -78 C for 30 min and then compound 3 (190 mg, 0.8 mmol) was added. The mixture was allowed to warm to room temperature. The reaction was followed by TLC (CHCl3/acetone, 85/15, v/v) at 30 min intervals. After stirring for 3 h at room temperature, when 3 was no longer detected by TLC, Et2O (20 mL) was added. The mixture was washed with H2O (5 mL) and evaporated to dryness. The residue was dissolved in 1,4-dioxane (6 mL) and CH2Cl2 (2 mL). Cu(OAc)2 (40 mg), NH3 (aq) (0.3 mL) and H2O (1 mL) were added. The mixture was stirred at room temperature for 1 d. The organic layer was separated, washed with H2O (10 mL), dried (MgSO4) and concentrated to dryness. Column chromatography of the residue (CHCl3/acetone, 85/15, v/v) gave 9 (70 mg, 39%), 10 (89 mg, 71%), and 11 (50 mg, 17%). 9: A white solid (mp >180 C, dec). deltaH (CDCl3, 200 MHz) 1.43-1.56 (16H, m), 1.90 (4H, m), 2.35 (4H, m), 3.29 (4H, m), 3.56 and 4.34 (8H, AB quartet, 2JAB 11.4 Hz); deltaC (CDCl3, 50 MHz) 22.34, 22.58, 25.42, 26.16, 27.48, 28.49, 36.98, 64.28, 66.43, 72.57, 98.80, 136.38; numax (KBr) 2936, 2860, 1496, 1448, 1380, 1240, 1156, 1044, 920; HRMS (EI, 70 eV) m/z calcd for C24H36O6N2 (M+) 448.2573, found 448.2557. 11: A white solid (mp 151-152 C). deltaH (CDCl3, 200 MHz) 1.34-1.84 (8H, m), 2.1 (2H, m), 2.39 (2H, m), 3.12 (2H, m), 3.63 and 4.57 (4H, AB quartet, 2JAB 11.4), 4.00 (3H, s), 4.02 (3H, s), 10.09 (1H, s); deltaC (CDCl3, 50 MHz) 22.39, 22.67, 25.49, 27.42, 28.21, 28.84, 37.29, 54.21, 55.19, 64.36, 72.23, 98.77, 105.98, 136.72, 159.26, 165.04, 167.74; numax (KBr) 2948, 2936, 1716, 1688, 1556, 1536, 1480, 1464, 1356, 1252, 1244, 1108; HRMS (EI, 70 eV) m/z calcd for C18H25O5N3 (M+) 363.1794, found 363.1812. The NMR spectra of 10 were consistent with those described: H. Pelissier, J. Rodriguez and K.P.C. Volhardt, Chem. Eur. J. 5 (1999), p. 3549. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (27)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,56686-16-9, its application will become more common.

Reference:
Article; Koszytkowska-Stawi?ska, Mariola; Mironiuk-Puchalska, Ewa; Sas, Wojciech; Tetrahedron Letters; vol. 52; 16; (2011); p. 1866 – 1870;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia