Tag: M.W:100-200

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.45588-79-2, name is 4-(Aminomethyl)pyrimidine, molecular formula is C5H7N3, molecular weight is 109.1292, as common compound, the synthetic route is as follows.category: pyrimidines

General procedure: Intermediate 1-2-1 Preparation of 4,4-dimethyl-6-oxo-N-phenyl-2-[(pyrimidin-4-ylmethyl)amino]cyclohex-1-ene-1-carbothioamideSynthesized according to Method B1. Intermediate 1 -1 -1 (906 mg) gave the desired product (500 mg, 34%) and 6,6-dimethyl-3-(phenylamino)-2-(pyrimidin-4-yl)-1 ,5,6,7- tetrahydro-4H-indol-4-one (34 mg, 6% Example 5) after preparative HPLC (XBrigde C18 5muetaiota 100×30 mm, Solvent: A = H20 + 0.2% Vol. NH3 (32%), B = Acetonitrile, 33% B in A to 56% in A over 5.5 min, flow: 70ml_/min). 1 H NMR (300 MHz, DMSO-d6) delta [ppm]= 0.90 – 1 .07 (m, 6 H) 2.39 (s, 2 H) 2.62 – 2.79 (m, 2 H) 4.96 (d, 2 H) 7.17 – 7.28 (m, 1 H) 7.39 (t, 2 H) 7.47 (d, 2 H) 7.55 (d, 1 H) 8.83 (d, 1 H) 9.18 (s, 1 H) 14.00 (br. s., 1 H) 14.58 (br. s., 1 H)Method B1 Preparation of 2-(amino)-6-oxocyclohex-1 -ene-1 -carbothioamides (Formula 1- 2)mixture of the 2-hydroxy-6-oxocyclohex-1 -ene-1 -carbothioamides (Formula 1 -1 ) and the 4-aminomethylheterocycle (Reagent B) was heated under an Argon atmospshere in either EtOH, EtOAc or DMSO optionally using 4A molecular sieves to remove water from the reaction mixture. The reaction was concentrated and purified either column chromatography or preparative HPLC.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,45588-79-2, 4-(Aminomethyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; GRAHAM, Keith; KLAR, Ulrich; BRIEM, Hans; HITCHCOCK, Marion; BAeRFACKER, Lars; EIS, Knut; SCHULZE, Volker; SIEMEISTER, Gerhard; BONE, Wilhelm; SCHROeDER, Jens; HOLTON, Simon; LIENAU, Philip; TEMPEL, Rene; SONNENSCHEIN, Helmut; BALINT, Jozsef; GRAUBAUM, Heinz; (577 pag.)WO2015/193339; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 94741-69-2 ,Some common heterocyclic compound, 94741-69-2, molecular formula is C5H3ClN4, 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 30 4-Amino-5-cyano-2-{4-[N-(3-hydroxy-2.2-dimethylpropyl)sulphamoyl]anilino}pyrimidine A solution of 4-amino-2-chloro-5-cyanopyrimidine (150 mg, 0.97 mmol), 4-[N-(3-hydroxy-2,2-dimethylpropyl)sulphamoyl]aniline (Method 4; 274 mg, 1.07 mmol) in NMP (5 ml) was heated at 120 C. for 24 hours. The mixture was allowed to cool, was diluted with water and extracted with ethyl acetate. The organic extracts were combined, dried and the solvent removed by evaporation. the residue was triturated with ether and the product collected by filtration to give the title compound (187 mg, 52%). NMR: 0.72 (s, 6H), 2.52 (d, 2H), 3.08 (d, 2H), 4.40 (t, 1H), 7.19 (t, 1H), 7.60 (s, 1H), 7.64 (d, 2H), 7.96 (d, 2H), 8.40 (s, 1H); m/z 375 (M-H)-.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,94741-69-2, its application will become more common.

Reference:
Patent; Thomas, Andrew Peter; US2003/87923; (2003); 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. 123240-66-4, name is N-(4,6-Dichloropyrimidin-5-yl)formamide, the common compound, a new synthetic route is introduced below. category: pyrimidines

4.3 (1S?,2S?,4S?)-4-(6-Chloro-9H-purin-9-yl)bicyclo[2.2.1]heptan-2-ol (9) A solution of 7 (2.3 g, 14 mmol), 4,6-dichloro-5-aminopyrimidine (3.4 g, 21 mmol) and DIPEA (7.9 mL, 56 mmol) in n-butanol (80 mL) was heated in a sealed microwave vessel at 160 C for 4 h. The resulting reaction intermediate was purified by chromatography on silica gel (toluene-ethyl acetate = 1:4), dissolved in a mixture of triethyl ortoformate (300 mL) and concd HCl (4 mL) and stirred at room temperature for 3-5 d, and then evaporated. This oily residue was dissolved in a mixture of THF and 1M hydrochloric acid (1:1, 125 mL) and stirred at rt for 4 h. After neutralization with sodium hydrogencarbonate, all volatiles were evaporated and the product was purified by column chromatography (ethyl acetate-toluene-acetone-ethanol 17:4:3:1) and crystallization from a toluene-cyclohexane mixture to afford 9 (2.1 g, 55%) as white crystals (mp = 155-157 C). 1H NMR (500 MHz, DMSO): delta 1.35 (dddd, 1H, Jgem = 12.4, J6en-5en = 9.2, J6en-5ex = 4.8, J6en-7b = 2.1, H-6endo), 1.75 (dm, 1H, Jgem = 12.4, H-3exo), 1.79 (tdd, 1H, Jgem = J6ex-5ex = 12.3, J6ex-1 = 5.1, J6ex-5en = 4.2, H-6exo), 1.90 (m, 1H, H-5exo), 2.01 (dddd, 1H, Jgem = 11.3, J5en-6en = 9.1, J5en-6ex = 4.1, J5en-7b = 2.3, H-5endo), 2.05 (dm, 1H, Jgem = 9.1, H-7a), 2.19 (dm, 1H, J1-6ex = 5.0, H-1), 2.49 (m, 1H, H-7b), 2.54 (ddd, 1H, Jgem = 12.5, J3en-2 = 6.9, J3en-7a = 2.4, H-3endo), 3.87 (m, 1H, H-2), 4.93 (d, 1H, JOH-2 = 3.5, OH), 8.71 (s, 1H, H-8′), 8.77 (s, 1H, H-2′). 13C NMR (125.8 MHz, DMSO): delta 24.04 (C-6), 32.65 (C-5), 37.57 (C-7), 42.69 (C-1), 45.85 (C-3), 65.17 (C-4), 72.67 (C-2), 131.72 (C-5′), 146.59 (C-8′), 149.37 (C-6′), 151.28 (C-2′), 152.43 (C-4′). ESI MS m/z (%): 265.2 (100) [M+H]. For C12H13N4OCl (262.69): calculated: 54.45; C, 4.95; H, 21.17; N, 13.39; Cl; found: 54.49; C, 5.08; H, 21.26; N, 12.99; Cl.

The synthetic route of 123240-66-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dejmek, Milan; Hrebabecky, Hubert; Sala, Michal; Dracinsky, Martin; Prochazkova, Eliska; Leyssen, Pieter; Neyts, Johan; Balzarini, Jan; Nencka, Radim; Bioorganic and Medicinal Chemistry; vol. 22; 11; (2014); p. 2974 – 2983;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 823-89-2, name is 5-Bromo-2-hydrazinopyrimidine. A new synthetic method of this compound is introduced below., SDS of cas: 823-89-2

5-Bromo-2-hydrazino-pyrimidine (1.02 g, 5.43 mmol) and 6-quinoline acetic acid (1.02 g, 5.43 mmol) were dissolved in dichloromethane (78 mL) and stirred at room temperature for 12 hours. The desired product was insoluble in dichloromethane and precipitated upon formation. The precipitate was filtered off and taken onto subsequent reactions as crude product, quinolin-6-yl-acetic acid N’-(5-bromo-pyrimidin-2-yl)-hydrazide (theoretical yield 1.94 g).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 823-89-2, 5-Bromo-2-hydrazinopyrimidine.

Reference:
Patent; SGX PHARMACEUTICALS, INC.; WO2008/144767; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 6299-25-8, 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 6299-25-8, name is 4,6-Dichloro-2-(methylthio)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Commercially available 4,6-dichloro-2-methylthiopyrimidine (1.00 g, 5.13 mmol) was dissolved in THF (10 mL) and the mixture was stirred at -78C for 1 hour after adding a 2 anol/L lithium diisopropylamide/THF-ethylbenzene solution (5.9 mL, 11.8 mmol) at -78C. The mixture was then stirred for 1.5 hours at room temperature after adding dry ice at -78C. Thereafter, 10% hydrochloric acid and ethyl acetate were added to separate the organic layer. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was reslurried with hexane, and the resulting solid was filtered off to give 4,6-diohloro-2-methylthiopyrimidine-5-oarboxylic acid (964 mg, 79%). ESI-MS: m/z 237 [M – H]-. 1H-NMR (CDCl3) delta(ppm): 2.60 (s, 3H), 9.68 (brs, 1H).

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 6299-25-8, 4,6-Dichloro-2-(methylthio)pyrimidine.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2163554; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 287714-35-6, 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.287714-35-6, name is Methyl 2-chloropyrimidine-5-carboxylate, molecular formula is C6H5ClN2O2, molecular weight is 172.57, as common compound, the synthetic route is as follows.

A solution of (2S)-2-propan-2-ylpiperazine (223 mg, 1.74 mmol) in dichloromethane (4.40 mL) was added to a stirred solution of methyl 2-chloropyrimidine-5-carboxylate (300 mg, 1.74 mmol) in dichloromethane (4.30 mL) at 25 C. N-Ethyl-N-propan-2-ylpropan-2-amine (0.752 mL, 4.35 mmol) was added. The resulting solution was stirred at room temperature for 18 h under a nitrogen atmosphere. The reaction mixture was concentrated and diluted with methanol. The crude product was purified by ion exchange chromatography, using a SCX column. The desired product was eluted from the column using 7M NH3/MeOH and fractions were evaporated to dryness to afford the desired compound (456.1 mg, 99%) as a yellow oil. This was used directly with no further purification. 1H NMR (399.9 MHz, DMSO-d6) delta 0.94-0.96 (6H, m), 1.58-1.66 (1H, m), 2.25-2.30 (1H, m), 2.56-2.63 (1H, m), 2.68-2.74 (1H, m), 2.95-3.02 (2H, m), 3.81 (3H, s), 4.56-4.60 (1H, m), 4.64-4.68 (1H, m), 8.78 (2H, s). MS: m/z 265 (MH+)

Statistics shows that 287714-35-6 is playing an increasingly important role. we look forward to future research findings about Methyl 2-chloropyrimidine-5-carboxylate.

Reference:
Patent; ASTRAZENECA AB; US2008/153812; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 39889-94-6, 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 39889-94-6 as follows.

Intermediate 174A (10mg, 0.021 mmol) in dichloromethane (1 mL) was added to a solution of 2-methylpyrimidin-5-amine (4.61 mg, 0.042 mmol) and pyridine (0.017 ml, 0.211 mmol) in dichloromethane (0.5 mL) dropwise. The reaction mixture was stirred at room temperature for 0.5 h, at which time LCMS and HPLC indicated a completion of reaction. The reaction mixture was diluted with EtOAc, washed with 0.5 N HC1. The organic layer was washed with brine, dried over sodium sulfate and concentrated. Thecrude was dissolved in DMSO and purified via preparative LC/MS (Method D: Gradient:45-90% B over 10 minutes, then a 5-minute hold at 100% B). Fractions containing the desired product were combined and dried via centrifugal evaporation to Example 174 (7.8 mg, 0.014 mmol, 67.6 % yield). ?H NMR (500MHz, DMSO-d6) 10.02 (br. s., 1H), 8.72 (s, 3H), 8.56 (s, 1H), 7.85 (d, J=11.3 Hz, 1H), 7.81 (s, 1H), 4.49-4.32 (m, 2H), 4.07 (s,3H), 3.57-3.29 (m, 2H), 2.62 (s, 3H), 2.54 (s, 3H), 1.60 (s, 3H). LC-MS: Method L, 0 to100% B. RT = 2.27 mm, MS (ESI) m/z: 547.15 (M+H). Analytical HPLC purity (method B): 100%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,39889-94-6, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; HALPERN, Oz Scott; JIANG, Wen; REZNIK, Samuel Kaye; RICHTER, Jeremy M.; (545 pag.)WO2018/13776; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 111196-81-7, name is 2-Chloro-5-ethylpyrimidine. A new synthetic method of this compound is introduced below., Quality Control of 2-Chloro-5-ethylpyrimidine

To a solution of 4-hydroxypiperidine (710 mg) in ethanol (5 mL) was added 5-ethyl-2-chloropyrimidine (425 muL), and the mixture was stirred at 80C overnight. To the reaction mixture was added water, and then the mixture was extracted with ethyl acetate, and the organic layer was dried over magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by column chromatography on silica gel (solvent; chloroform/methanol = 100/0 to 90/10) to give 1-(5-ethylpyrimidin-2-yl)piperidin-4-ol (699 mg) as a colorless solid (yield: 96%). MS(APCI)m/z; 208[M+H]+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 111196-81-7, 2-Chloro-5-ethylpyrimidine.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; EP2390254; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 611-08-5, Adding some certain compound to certain chemical reactions, such as: 611-08-5, name is 5-Nitrouracil,molecular formula is C4H3N3O4, 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 611-08-5.

Step 178.5: 1 ,3-Dimethyl-5-nitro-1 H-pyrimidine-2,4-dione The title compound was prepared in analogy to the procedure described for step 100.5 but using 5- nitrouracil. The reaction was performed at rt for 20 h. The reaction mixture was concentrated and triturated in CH2CI2. The resulting suspension was filtered and the solid was purified by flash chromatography (CH2CI2/MeOH, 94:6). tR: 0.41 min (LC-MS 2); ESI-MS: 186.1 [M+H]+ (LC-MS 2); Rf = 0.55 (CH2CI2/MeOH, 9:1 ).

According to the analysis of related databases, 611-08-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; GUAGNANO, Vito; HOLZER, Philipp; KALLEN, Joerg; LIAO, Lv; MAH, Robert; MAO, Liang; MASUYA, Keiichi; SCHLAPBACH, Achim; STUTZ, Stefan; VAUPEL, Andrea; WO2013/111105; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 63200-54-4, 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.63200-54-4, name is 2,4-Dichloro-5H-pyrrolo[3,2-d]pyrimidine, molecular formula is C6H3Cl2N3, molecular weight is 188.0141, as common compound, the synthetic route is as follows.

General procedure: 2,4-dichloro-1H-pyrrolo[3,2-d]pyridine (5) was dissolved in a solution of 1:1 THF:DMF underN2. Sodium hydride (60% suspension in oil) was added directly, and the mixture was stirredat room temperature for 1 h. Appropriate halogenated reagent (methanesulfonyl chloride (6),2-nitrobenzenesulfonyl chloride (7), 2,4,6-Triisopropylbenzenesulfonyl chloride (8), benzyl bromide(9), 2,4-dichlorobenzyl bromide (10), 4-methoxybenzyl chloride (11), acetyl chloride (12), isobutyrylchloride (13), diphenylcarbamyl chloride (14), iodoethane (15)) was added and the mixture was stirredat r.t. for 18 h. The solvent was removed and residue dissolved in EtOAc and washed with waterand brine, then dried over MgSO4. Organics were loaded onto Celite and product purified usingsilica column chromatography eluting with 4:1 hexanes:EtOAc or 9:1 DCM:MeOH to obtain product,generally as a white to o-white solid.4.3.4. Characterization2,4-dichloro-5-(methylsulfonyl)-5H-pyrrolo[3,2-d]pyrimidine (6). 1H-NMR (400 MHz, CDCl3) (ppm) : 3.66(s, 3H); 6.83 (d, J = 4.12 Hz, 1H); 8.10 (d, J = 4.12 Hz, 1H). 13C-NMR (100 MHz, DMSO-d6): 158.79,153.40, 152.14, 144.44, 139.10, 137.58, 124.23, 123.05, 105.97, 102.31, 44.88. ESI-MS m/z for C7H5Cl2N3O2Scalcd. at 264.95, found at 266.01 [M + H]+. Anal. calcd. for C7H5Cl2N3O2S: C, 31.60; H, 1.89; N, 15.79.Found: C, 31.58; H, 1.89; N, 15.78.

The chemical industry reduces the impact on the environment during synthesis 63200-54-4, I believe this compound will play a more active role in future production and life.

Reference:
Article; Cawrse, Brian M.; Robinson, Nia’mani M.; Lee, Nina C.; Wilson, Gerald M.; Seley-Radtke, Katherine L.; Molecules; vol. 24; 14; (2019);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia