Tag: M.W:200-300

Electric Literature of 31169-25-2, 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 31169-25-2, name is 7-Bromothieno[3,2-d]pyrimidin-4(3H)-one. This compound has unique chemical properties. The synthetic route is as follows.

Dimethylformamide (25.8 mL, 0.33 mol) and dichloromethane (150 mL) were placed in a reaction vessel, to which a dilution of oxalyl chloride (46.4 mL, 0.53 mol) in dichloromethane (150 mL) was then added over about 30 min. Subsequently, 7- bromothieno[3,2-d]pyrimidin-4(3H)-one (35 g, 0.15 mol) was added, and heated under reflux for 3 hrs. Thereafter, the reaction mixture was quenched before water was added carefully. The Organic layer thus formed was isolated, while the aqueous layer was extracted with dichloromethane. The organic layers were pooled and dried over anhydrous sodium sulfate, and the dried organic layer was subjected to vacuum filtration and vacuum distillation, followed by desiccation with a nitrogen gas to obtain the desired compound (30.5 g, 85percent). ‘H-NMR^OOMHz, DMSO-d6): delta 9.16(s, 1H), 8.79(s, 1H).

According to the analysis of related databases, 31169-25-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HANMI PHARM. CO., LTD.; BANG, Keuk Chan; PARK, Chang Hee; CHOI, Jae Yul; KIM, Seo Hee; HAM, Young Jin; WO2014/3483; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 857641-46-4, 2-(4-Bromo-1H-pyrazol-1-yl)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, Recommanded Product: 2-(4-Bromo-1H-pyrazol-1-yl)pyrimidine, blongs to pyrimidines compound. Recommanded Product: 2-(4-Bromo-1H-pyrazol-1-yl)pyrimidine

A solution containing 2-(4-bromo-pyrazol-1-yl)-pyrimidine (300 mg, 1.34 mmol), 4-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (280 mg, 1.34 mmol), PdCI2(dppf) (95 mg, 0.13 mmol) and potassium phosphate (800 mg, 4 mmol) in dioxane was heated at 80 C under argon for overnight. After removed the solvent, ethylacetate was added and the mixture was filtered, washed with water.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,857641-46-4, 2-(4-Bromo-1H-pyrazol-1-yl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; SCHERING CORPORATION; WO2008/153858; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 98141-42-5, 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.98141-42-5, name is 4,6-Dichloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine, molecular formula is C6H4Cl2N4, molecular weight is 203.03, as common compound, the synthetic route is as follows.

Experimental for the Preparation of 1-Substituted-4-phenoxy-6-aryl-1H-pyrazolo[3,4-d]pyrimidine (Scheme 5)To a solution of the dichloride (2.53 mmol) dissolved in DMSO (5 mL) was added by drops a solution of phenol (0.7 eq) and NaH (0.7 eq) that had stirred for 30 minutes. The reaction mixture was stirred for 5 hr at room temperature and then used as a DMSO solution for the next step. To the portion of the product used (0.25 mmol) was added with the desired aryl boronic acid (1.5 eq), Na2CO3 solution (2 eq), and Pd(PPh3)4 (catalytic amount). The reaction heated at 150 C. for 16 hrs. The crude reaction then filtered purified via preparatory HPLC using a Gilson instrument.

The chemical industry reduces the impact on the environment during synthesis 98141-42-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Wyeth; US2010/15141; (2010); 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. 784150-41-0, name is 6-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine, the common compound, a new synthetic route is introduced below. Formula: C6H3BrClN3

A mixture of 6-bromo-4- chloro-7/-/-pyrrolo[2,3-c]pyrimidine (232 mg, 1 mmol), PhB(OH)2 (365 mg, 3 mmol), Cu(OAc)2 (363 mg, 2 mmol) and 1 , 10-phenanthroline (360 mg, 2 mmol) was stirred in DMF (20 mL) for 16 h before the reaction was diluted with saturated NH4CI(aq) (200 mL) and water (200 mL). The resulting mixture was extracted with EtOAc (3 x 50 mL), the combined organic phases were passed through a phase separator, concentrated in vacuo, and the residue was purified by flash chromatography (40 g GraceResolv silica, 0-60% EtOAc in cyclohexane) to give the title compound (170 mg, 55%) as colourless solid. LCMS (Method B): RT = 1.42 min, m/z = 308, 310, 312 [M+H]+.

The synthetic route of 784150-41-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMAC DISCOVERY LIMITED; O’DOWD, Colin; HARRISON, Tim; HEWITT, Peter; ROUNTREE, Shane; HUGUES, Miel; BURKAMP, Frank; JORDAN, Linda; HELM, Matthew; BROCCATELLI, Fabio; CRAWFORD, James John; GAZZARD, Lewis; WERTZ, Ingrid; LEE, Wendy; (304 pag.)WO2018/73602; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 151266-23-8, 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.151266-23-8, name is 3-Iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine, molecular formula is C5H4IN5, molecular weight is 261.02, as common compound, the synthetic route is as follows.

Compound 2-4 is synthesized as shown in Scheme 2. Compound 1-3 is reacted with isopropyl bromide in dimethylformamide with potassium carbonate at 800C, to provide the 1 -isopropyl pyrazolopyrimidine 2-1. This intermediate with the protected indolyl boronic acid species 2-2, using tetrakistriphenylphosphine palladium catalysis in DME-water solvent at 800C for 4-5 hours, to produce the Suzuki coupling product, compound 2-3. Removal of the protecting groups with acid in dioxane yields the product, 2-( 4-amino-lH-pyrazolo[3,4-d]pyrimidin-3-yl iodide (Cpd. 2-4).

Statistics shows that 151266-23-8 is playing an increasingly important role. we look forward to future research findings about 3-Iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine.

Reference:
Patent; INTELLIKINE, INC.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; WILSON, Troy, Edward; MARTIN, Michael; ROMMEL, Christian; WO2010/6086; (2010); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 18740-39-1, Adding some certain compound to certain chemical reactions, such as: 18740-39-1, name is 2,4-Dichlorothieno[2,3-d]pyrimidine,molecular formula is C6H2Cl2N2S, 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 18740-39-1.

Example 9 2,4-Bis(2-methylphenylamino)thieno[2,3-d]pyrimidine 2,4-Dichlorothieno[2,3-d]pyrimidine (1.5 g, 0.0073 mol) and o-toluidine (5 ml) were heated in an oil bath at 160° for 2 hours. The reaction mixture was dissolved in chloroform (200 ml) and washed with 2N hydrochloric acid (3 x 100 ml), then sodium carbonate solution, dried over magnesium sulphate, filtered and evaporated under reduced pressure to give a solid, (1.98 g). The solid was purified by column chromatography using dichloromethane as eluant. The fractions containing the product were combined and evaporated under reduced pressure to give a solid. Recrystallization from diethyl ether/petroleum ether (b.p. 40-60°) gave the title compound, (1.0 g), m.p. 121-123°, References for starting materials

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. 18740-39-1, 2,4-Dichlorothieno[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SMITHKLINE BEECHAM INTERCREDIT B.V.; EP404356; (1990); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.2134-36-3, name is Ethyl 4-chloro-2-methylpyrimidine-5-carboxylate, molecular formula is C8H9ClN2O2, molecular weight is 200.62, as common compound, the synthetic route is as follows.Formula: C8H9ClN2O2

A suspension of ethyl 4-chloro-2-methylpyrimidine-5-carboxylate (1.00 g) and O-benzylhydroxylamine hydrochloride (1.35 g) in N-ethyldiisopropylamine (16 mL) was heated with stirring at 110 to 120C for 3 hours. After cooling of the reaction mixture, chloroform and water were added thereto, followed by separation of an organic layer. An aqueous layer was extracted with chloroform, combined with the organic layer and dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 90-50% hexane/ethyl acetate] to obtain a yellow oil of ethyl 4-((benzyloxy)amino)-2-methylpyrimidine-5-carboxylate (990 mg). 1H-NMR (CDCl3) delta value: 1.35 (t, J=7.2 Hz, 3H), 2.67 (s, 3H), 4.31 (q, J=7.2 Hz, 2H), 5.05 (s, 2H), 7.35-7.44 (m, 3H), 7.46-7.51 (m, 2H), 8.79 (s, 1H), 10.20 (brs, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2134-36-3, Ethyl 4-chloro-2-methylpyrimidine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Toyama Chemical Co., Ltd.; KAWAI, Hyouei; MURATA, Daigo; SUZUMURA, Yuko; EP2810944; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 13162-43-1, 4,6-Dichloro-2-methyl-5-nitropyrimidine, 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: 13162-43-1, blongs to pyrimidines compound. SDS of cas: 13162-43-1

General procedure: 10% Pd/C(0.05) gwas added to the solution of substituted pyrimidine (4.48mmol) in ethyl acetate (EA, 20mL) in Parr hydrogenater. Then, replace the air with nitrogen three times, and react for 4hat room temperature in normal pressure. Filter the solution to remove Pd/C through Celite filter agent, the filtrate was concentrated to yield the intermediates 11a,b [46]. 5.4.1 4,6-Dichloro-2-methyl-5-nitropyrimidine (11a) Pale solid; Yield: 84.0%; MS (ESI) m/z: 177.94 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13162-43-1, 4,6-Dichloro-2-methyl-5-nitropyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Huang, Daowei; Huang, Lei; Zhang, Qingwei; Li, Jianqi; European Journal of Medicinal Chemistry; vol. 140; (2017); p. 212 – 228;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 109229-22-3, 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. 109229-22-3, name is 6-Benzyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4(3H)-one. A new synthetic method of this compound is introduced below.

Preparation 26-Benz l-4-bromo-5,6,7,8-tetrahydropyrido[4,3-rf]pyriniidinePOBr3 (8.92 g, 21 x 1.5mmol) was added to a slurry of the title compound from Preparation 1 (5 g, 21 mmol) in dichloroethane (100 mL). The mixture was stirred at room temperature for 1 h and then refluxed and stirred for a further 1 h, during which time the course of the reaction was monitored by TLC (Merck UV-254; chloroform/methanol 10:1; samples were treated with saturated Na2C(? solution). The reaction mixture was cooled to room temperature, treated with saturated Na2CC>3 solution, stirred for 10 min and treated with ultrasound for 10 min. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layers were combined, washed with water, dried over MgS04 and evaporated to give the product in 79% (5 g) yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,109229-22-3, 6-Benzyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER, INC.; LONG, Scott, A.; THORARENSEN, Atli; SCHNUTE, Mark, E.; WO2013/54185; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 10397-13-4 ,Some common heterocyclic compound, 10397-13-4, molecular formula is C8H9Cl2N3O, 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 2 6-(4-Methanesulfonyl-piperazin-l-vI)-2-morphoHn-4-yl-[4,5’lbipyriinidinyl-2′-ylamine (4) A mixture of Intermediate Al (198mg), Intermediate G (230mg) and potassium carbonate (293mg) was stirred in acetonitrile (10ml) at room temperature. After 24 hours the reaction mixture was diluted with ethyl acetate, washed with water, dried (MgSO4) and the solvent removed in vacuo. The residue was recrystallised from ethyl acetate/hexane to yield 4-[4-chloro-6-(4-methanesulfonyl-piperazin-l-yl)-yrimidin-2- yl]-morpholine (206mg). Reaction of 4-[4-chloro-6-(4-methanesulfonyl-piperazin- 1 -yl)-yrimidin-2-yl]- morpholine with 2-aminopyrimidine-5-boronic acid, pinacol ester using standard Suzuki conditions yielded the desired title compound. IH NMR (400MHz, CDCl3) 2.80 (3H,s), 3.28-3.24 (4H,m), 3.82-3.75 (12H,m), 5.20 (2H,s,br.), 6.16 (lH,s), 8.91 (2H,s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10397-13-4, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; WO2009/66084; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia