Tag: M.W:100-200

93366-88-2, 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. 93366-88-2, name is 7H-Pyrrolo[2,3-d]pyrimidin-2-amine. A new synthetic method of this compound is introduced below.

7H-pyrrolo[2,3-d]pyrimidin-2-amine (388 mg, 2.90 mmol), 4-bromo-2-iodo-1-methoxybenzene (2.56 g, 8.64mmol), potassium carbonate (1.66) Mg, 12.03 mmol) and valine (83 mg, 0.72 mmol) were added to an eggplantflask, dimethyl sulfoxide was added, and the reaction solution was deoxidized. Copper iodide (60 mg, 0.31mmol) was added and the reaction solution was deoxygenated. Heat to 90C and stir for 16 hours. After the reaction was completed, it was cooled to room temperature, water and ethyl acetate were added, and the mixturewas filtered over Celite. The target compound was obtained in 60 mg.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,93366-88-2, 7H-Pyrrolo[2,3-d]pyrimidin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhao Yujun; Li Zhiqiang; Yan Ziqin; Li Jia; Zhou Yubo; Su Mingbo; Chen Zheng; (138 pag.)CN109810110; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

7504-94-1, 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 7504-94-1, name is 2-Hydrazinylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

After adding 230 mg of 2-hydrazinopyrimidine and 293 mul of triethylamine to a 50 ml DMF solution containing 983 mg of {2-(3-ethoxy-4-methoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester, the mixture was stirred at 85 C. for 10 hours under a nitrogen atmosphere. The reaction mixture was concentrated, and the residue was dissolved in 30 ml of a methanol_THF=1:1 mixed solvent. After adding 420 mul of acetic acid and 657 mg of sodium cyanotrihydroborate to the reaction mixture, it was stirred at room temperature for 5 hours. Ethyl acetate was added to the reaction mixture which was then filtered through a small amount of NAM silica gel, and the silica gel was washed with ethyl acetate-methanol. The filtrate was concentrated under reduced pressure, and the residue was purified by NAM silica gel column chromatography (methanol-ethyl acetate) to give the title compound (400 mg) as a light yellow solid. 1H-NMR (CDCl3) delta 1.32 (t, J=7.2 Hz, 3H) 2.58 (s, 3H) 3.80 (s, 3H) 3.90 (q, J=7.2 Hz, 2H) 5.77 (d, J=7.2 Hz, 1H) 6.77 (d, J=8.8 Hz, 1H) 6.83 (d, J=8.8 Hz, 2H) 7.12-7.17 (m, 3H) 7.81 (d, J=8.8 Hz, 2H) 8.69 (d, J=4.8 Hz, 2H)

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 7504-94-1, 2-Hydrazinylpyrimidine.

Reference:
Patent; Eisai R&D Management Co., Ltd.; US2008/15199; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

3934-20-1, 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 3934-20-1 as follows.

Phenylboronic acid (1 eq) and 2,4-dichloropyrimidine (1 eq) were added to tetrahydrofuran, to which 10% sodium bicarbonate (1 eq) was added. Nitrogen was bubbled into the mixture to remove oxygen while the reaction mixture was well stirred. 0.05 equivalent of palladium tetrakis was added to the mixture and stirred well. The mixture was then refluxed under a stream of nitrogen for 24 hours. After the reaction was complete, the mixture was worked up with ethyl acetate and water to give a crude yellow solid. The solid was purified by column chromatography to give white solid crystals. TLC was observed at Rf: 05 (ethyl acetate: hexane)

The chemical industry reduces the impact on the environment during synthesis 3934-20-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; CHUNGNAM NATIONAL UNIVERSITY INDUSTRY & ACADEMIC COOPERATION (IAC); JUNG, SANG HUN; WOO, SUN HEE; KIM, SANG KYUM; JEON, EUN SEOK; LEE, YOU JUNG; MANICKAM, MANOJ; JALANI HITESHKUMAR, HITESHKUMAR; SHARMA, NITI; (234 pag.)KR2015/111825; (2015); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding some certain compound to certain chemical reactions, such as: 871254-61-4, name is 2,4-Dichloropyrimidine-5-carbaldehyde, 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 871254-61-4. 871254-61-4

Example 18 6-Chloro-1H-pyrazolo[3,4-d]pyrimidine To a stirred solution of hydrazine (Aldrich, 64 mg, 2 mmol) in THF (5 mL), 2,4-Dichloro-pyrimidine-5-carbaldehyde (Example 17, 176 mg, 1 mmol) was added and the mixture was stirred at room temperature for 30 min. The mixture was poured into water and extracted with EtOAc. The extract was dried with sodium sulfate and the solvent was removed to give an orange solid. 128 mg, 82%. MS (M+H)+, 155.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 871254-61-4.

Reference:
Patent; Ding, Qingjie; Jiang, Nan; Roberts, John Lawson; US2005/277655; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

5413-85-4 , The common heterocyclic compound, 5413-85-4, name is 5-Amino-4,6-dichloropyrimidine, molecular formula is C4H3Cl2N3, 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.

2C. 5,6-Diamino-4-chloropyrimidine; A mixture of 4,6-dichloro-5-aminopyrimidine (Aldrich Chemical Co.) (2.0 g, 12.2 mmol) and concentrated aqueous ammonia (20 ml) was heated to 100 0C in a sealed glass tube with vigorous stirring for 18 hours. The cooled tube was recharged with concentrated aqueous ammonia (8 ml), aggregates were broken up, and the mixture was reheated at 100 0C for a further 28 hours. The mixture was evaporated to dryness and the solids were washed with water (20 ml) and dried to give the product as yellow crystals (1.71 g, 97percent). LC/MS (LCTl): Rt 1.59 [M+H]+ 147, 145.

According to the analysis of related databases, 5413-85-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; THE INSTITUTE OF CANCER RESEARCH:ROYAL CANCER HOSPITAL; CANCER RESEARCH TECHNOLOGY LIMITED; ASTRAZENECA AB; WO2008/75110; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

2435-50-9 ,Some common heterocyclic compound, 2435-50-9, molecular formula is C5H4N2O, 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: SI, Figure 4. General procedure of the reductive amination reactions: synthesis of AA9-AA24 compounds (Tables 1 and 2). The ethyl 3-amino-4-(cyclohexylamino)benzoate (AA1) and derivatives (1 equiv.)and benzaldehyde (1 equiv) were heated in DCE for 1h at 80 oC in the presence of molecular sieves (4 A), then the mixture was cooled down to room temperature before addition of the NaBH(OAc)3 (1.6 equiv.) in small portions over 3h. The reaction mixture was stirred at room temperature under a nitrogen atmosphere for 17h. The reaction mixture was quenched with aqueous saturated NaHCO3, and the product was extracted with EtOAc. The EtOAc extract was dried (MgSO4), and the solvent was evaporated. The residue was purified by flash-column chromatography on silica gel, using a mixture of solvent of DCM: MeOH (50:1), to provide the desired AA9-AA24 compounds (Tables 1-2).

According to the analysis of related databases, 2435-50-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Iniguez, Eva A.; Perez, Andrea; Maldonado, Rosa A.; Skouta, Rachid; Bioorganic and Medicinal Chemistry Letters; vol. 25; 22; (2015); p. 5315 – 5320;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

63200-54-4, Adding a certain compound to certain chemical reactions, such as: 63200-54-4, 2,4-Dichloro-5H-pyrrolo[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, 63200-54-4, blongs to pyrimidines compound.

2-Chloro-4-(4-cyclopropyl-2,6-dimethylphenoxy)-5H-pyrrolo[3,2-Patent; VALEANT RESEARCH & DEVELOPMENT; WO2006/122003; (2006); A2;,
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. 60025-09-4, name is 4-Amino-6-chloropyrimidine-5-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows. 60025-09-4

4- Amino-6-(((lS, lR)-l-(3-(2-pyridinyl)-l,6-naphthyridin-2-yl)ethyl)amino)-5- pyrimidinecarbonitrile; To a stirred solution of l-(3-(pyridin-2-yl)-l,6-naphthyridin-2-yl)ethanamine (15 mg, 0.060 mmol) in butanol (1.5 mL) was added 4-amino-6-chloropyrimidine-5- carbonitrile (9.26 mg, 0.060 mmol) and N-ethyl-N-isopropylpropan-2-amine (20.9 uL, 0.120 mmol). The reaction was heated at 120 C for 2 h. After this time the reaction was cooled to r.t. The resulting precipitate was filtered and washed with hexanes to give racemic 4-amino-6-(((lS, lR)-l-(3-(2-pyridinyl)-l,6- naphthyridin-2-yl)ethyl)amino)-5-pyrimidinecarbonitrile. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 9.33 (1 H, s), 8.83 (2 H, d, J=5.9 Hz), 8.33 (1 H, s), 8.14 (1 H, s), 8.02 (1 H, d, J=5.9 Hz), 7.93 (1 H, td, J=7.7, 1.8 Hz), 7.64 (2 H, d, J=7.8 Hz), 7.44 (1 H, ddd, J=7.6, 4.9, 1.0 Hz), 6.15 (1H, m), 5.28 (2 H, bs), 1.38 – 1.43 (3 H, m). Mass Spectrum (ESI) m/e = 251.0. Mass Spectrum (ESI) m/e = 369.2 (M+l).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,60025-09-4, 4-Amino-6-chloropyrimidine-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; CHEN, Yi; CUSHING, Timothy, D.; FISHER, Benjamin; GONZALEZ LOPEZ DE TURISO, Felix; HAO, Xiaolin; SHIN, Youngsook; WO2012/87784; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

45588-79-2, 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. 45588-79-2, name is 4-(Aminomethyl)pyrimidine. A new synthetic method of this compound is introduced below.

To a stirred solution of 4-(cis-8-(dimethylamino)-3-oxo-8-phenyl-2-azaspiro[4. 5]decan-2- yI)-2,2-dimethylbutanoic acid hydrochloride (300mg, 0.71 mmol) in THF(1 0mL), diisopropylethylamine (490mg, 3.8Ommol) and HATU (541mg, 1 .43mmol) were added at RT. The reaction mixture was stirred at RT for 45mm and then pyrimidin-4-yl- methanamine (114mg, 1 .O45mmol) was added at 0C. The reaction mixture was warmedto RT and stirred for 16h. The reaction mixture was quenched with saturated NaHCO3 Solution, extracted with 10%methanol in DCM (3X25mL). The combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the crude compound. Purification by column chromatography over silica gel (100-200 mesh) by using 1 0%methanol in DCM with traces of ammonia as eluent to give 160mg ofcompound which was further purified by preparative TLC by using 5% methanol in DCM as mobile phase to give 110 mg (33%) of cis- 4-(8-Dimethylamino-3-oxo-8-phenyl-2- azaspiro[4.5]decan-2-yl)-2,2-dimethyl-N-(pyrimidin-4-yl-methyl)-butyramide as solid.

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. 45588-79-2, 4-(Aminomethyl)pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GRUeNENTHAL GMBH; WEGERT, Anita; KUeHNERT, Sven; KOENIGS, Rene, Michael; NOLTE, Bert; LINZ, Klaus; HARLFINGER, Stephanie; KOeGEL, Babette-Yvonne; RATCLIFFE, Paul; THEIL, Fritz; GROeGER, Olga; BRAUN, Birgit; (223 pag.)WO2016/8582; (2016); 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. 51752-67-1, name is 4-Chloropyrido[3,4-d]pyrimidine, the common compound, a new synthetic route is introduced below. 51752-67-1

EXAMPLE 24 (3-Ethynyl-phenyl)-pyrido[3,4d]pyrimidin4-yl-amine To 4-chloro-pyrido[3,4-d]pyrimidine (250 mg, 1.50 mmol) in N-methylpyrrolidin-2-one (0.5 mL) was added 3-ethynylaniline (212 mg, 1.81 mmol) and pyridine (237 mg, 3.0 mmol). The mixture was heated to 80 C. under an atmosphere of dry N2(g) for 3 hours. The reaction mixture was dissolved in CHCl3 and washed with saturated aqueous Na2CO3, and brine. The organic phase was dried over Na2SO4, concentrated in vacuo, and flash chromatographed on silica with a gradient of 40% to 70% acetone/hexanes to afford 120 mg of product. This material was precipitated as its hydrochloride salt by dissolution in minimal CHCl3, titration with HCl (1 eq.) in diethyl ether, and dilution with diethyl ether.

The synthetic route of 51752-67-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARNOLD, LEE DANIEL; MOYER, MIKEL PAUL; SOBOLOV-JAYNES, SUSAN BETH; US2002/45630; (2002); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia