Pyrimidines

Electric Literature of 157335-93-8, 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. 157335-93-8, name is 4,6-Dimethylpyrimidine-5-carboxylic acid, molecular formula is C7H8N2O2, 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.

Step L 5-[(4-(3S)-4-[(1R,2R)-2-Ethoxy-5-(trifluoromethyl)-2,3-dihydro-1H-inden-1-yl]-3-methylpiperazin-1-yl-4-methylpiperidin-1-yl)carbonyl]-4,6-dimethylpyrimidine dihydrochloride t-Butyl 4-(3S)-4-[2-ethoxy-5-(trifluoromethyl)-2,3-dihydro-1H-inden-1-yl]-3-methylpiperazin-1-yl-4-methylpiperidine-1-carboxylate (48.4 g, 0.0921 mol) was treated with a 4.0 M solution of hydrogen chloride in 1,4-dioxane (230 mL) at room temperature for 1 h. The reaction mixture was concentrated to dryness and the residue was further dried under high vacuum. The formed amine hydrochloride was mixed with 4,6-dimethyl-pyrimidine-5-carboxylic acid (16.8 g, 0.110 mol) in methylene chloride (100 mL), and then 1-hydroxybenzotriazole (16.80 g, 0.1243 mol), N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (25.00 g, 0.1304 mol) and triethylamine (65.0 mL, 0.466 mol) were added. The resulting reaction mixture was stirred at room temperature overnight before it was diluted with methylene chloride and washed with aqueous sodium hydroxide (1 M) and brine. The organic layer was collected and dried over magnesium sulfate. After removal of the solvent, the residue was dissolved in methylene chloride (50 mL) and the solution was passed through a silica plug with ethyl acetate containing 1% triethylamine. The solution was concentrated and the residue was dissolved in 900 mL of isopropyl acetate. To the above solution, 185 mL of 1.0 N HCl in isopropyl acetate was slowly added. The mixture slowly turned cloudy, and was stirred overnight. The formed white solid was collected, washed with 40 ml, of isopropyl acetate. The cake was air-dried to give 47.0 g (80.7%) of product. MS (EI) 560.3 (M+1).

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 157335-93-8, 4,6-Dimethylpyrimidine-5-carboxylic acid.

Reference:
Patent; Xue, Chu-Biao; Cao, Ganfeng; Huang, Taisheng; Chen, Lihua; Zhang, Ke; Wang, Anlai; Meloni, David; Anand, Rajan; Glenn, Joseph; Metcalf, Brian W.; US2005/261310; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 69034-12-4 ,Some common heterocyclic compound, 69034-12-4, molecular formula is C5H2ClF3N2, 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: To a solution of 25a (200 mg, 0.458 mmol) in NMP (4 ml)was added 2-chloro-5-(trifluoromethyl)pyrimidine (100 ng,0.549 mmol) and K2CO3 (189 mg, 1.374 mmol) at room temperature.The reaction mixture was heated at 90 C for 3 h. After cooling to room temperature, the reaction mixture was diluted with water.The aqueous layer was separated and then extracted with EtOAc. The combined organic extracts were washed with water and brine,dried over Na2SO4, filtered, and concentrated. The residue was purified by flash column chromatography (silica gel: CHCl3/MeOH = 95/5) to afford 26a

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. 69034-12-4, 2-Chloro-5-(trifluoromethyl)pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Tsuno, Naoki; Yukimasa, Akira; Yoshida, Osamu; Suzuki, Shinji; Nakai, Hiromi; Ogawa, Tomoyuki; Fujiu, Motohiro; Takaya, Kenji; Nozu, Azusa; Yamaguchi, Hiroki; Matsuda, Hidetoshi; Funaki, Satoko; Yamanada, Natsue; Tanimura, Miki; Nagamatsu, Daiki; Asaki, Toshiyuki; Horita, Narumi; Yamamoto, Miyuki; Hinata, Mikie; Soga, Masahiko; Imai, Masayuki; Morioka, Yasuhide; Kanemasa, Toshiyuki; Sakaguchi, Gaku; Iso, Yasuyoshi; Bioorganic and Medicinal Chemistry; vol. 25; 7; (2017); p. 2177 – 2190;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 40805-79-6, 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. 40805-79-6, name is 5-Pyrimidinecarbonitrile, molecular formula is C5H3N3, 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.

3-Bromo-pyridine (0.92 ml; 9.51 mmol; 2.00 eq.) and anhydrous THF (8 mL) are added in a dry flask. The solution is purged with nitrogen for 30 min. Isopropylmagnesium chloride/LiCI solution 1 .3 M in THF (7.32 mL; 9.51 mmol; 2.00 eq.) is added dropwise to the reaction flask over a period of 10 min, and the mixture is stirred for 4 h at RT. The resulting solution of 3- pyridylmagnesium bromide is treated with solid pyrimidine-5-carbonitrile (0.50 g; 4.76 mmol; 1.00 eq.) at RT and to the resulting mixture NaBH4 (0.72 g; 19.03 mmol; 4.00 eq.) is added, followed by water (0.2 mL, after 30 minutes) The mixture is stirred overnight. Next portion of water (10 mL) is added and the mixture concentrated in vacuo. The residue is dissolved in EtOAc and filtered. Oily residue is purified by FCC (DCM/MeOH; gradient) provided C- pyridin-3-yl-C-pyrimidin-5-yl-methylamine (100.00 mg; yield 1 1.3 %; yellow oil).

According to the analysis of related databases, 40805-79-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SELVITA S.A.; FABRITIUS, Charles-Henry Robert Yves; NOWAK, Mateusz Oktawian; WIKLIK, Katarzyna Anna; SABINIARZ, Aleksandra Barbara; BIE?, Marcin Dominik; BUDA, Anna Ma?gorzata; GUZIK, Pawel Szczepan; JAKUBIEC, Krzysztof Roman; MACIUSZEK, Monika; KWIECI?SKA, Katarzyna; TOMCZYK, Mateusz Micha?; GA??ZOWSKI, Micha? Miko?aj; GONDELA, Andrzej; DUDEK, ?ukasz Piotr; (681 pag.)WO2016/180536; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1753-50-0, 2-Chloropyrimidine-5-carbonitrile, 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: C5H2ClN3, blongs to pyrimidines compound. Formula: C5H2ClN3

Step 24A: 2-r(3R.5R)-3.5-dimethylpiperazin-l-yllpyrimidine-5-carbonitrile (0915) To a suspension of (2R,6R)-2,6-dimethylpiperazine dihydrochloride (0.250 g, 1.34 mmol, 1.0 eq) and 2-chloropyrimidine-5-carbonitrile (0.187 g, 1.34 mmol, 1.0 eq) in acetonitrile (5 mL) was added triethylamine (0.93 mL, 6.7 mmol, 5.0 eq) and reaction mixture stirred at room temperature overnight. The resulting suspension was filtered to remove triethylamine hydrochloride and concentrated to yield 2-[(3R,5R)-3,5-dimethylpiperazin-l-yl]pyrimidine-5-carbonitrile 24a as an orange solid. The crude material was carried to Example 26 without further purification.

The synthetic route of 1753-50-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; HARRIOTT, Nicole; PAGANO, Nicholas; (135 pag.)WO2017/79641; (2017); 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 65996-58-9, name is 2-Amino-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H6N4O

General procedure: Amixture of 9-deazapurine 5 (150.0 mg, 1.0 mmol) and benzoylchloride (2.2 equiv) in trifluoromethanesulfonic acid (3.45 g,23 mmol) was stirred at 80-120 C for 48 h. After the mixturewas cooled and H2O (15 mL) was added. Then the reaction wasneutralized with NaOH 1.0 mol/L, the volume adjusted to approximately35 mL by adding H2O and then 60 equiv of NaOH wereadded. The reaction was stirred for 2.5 h at 60 C. The mixturewas neutralized with glacial acetic acid and the formed solid wasfiltered under vacuum and washed several times with dichloromethane(10 mL), ethyl acetate (10 mL), acetone (5 mL) andmethanol (5 mL). The precipitate purity was monitored by CCDand depending on the product, further purification was necessaryby recrystallization in methanol or flash chromatography usingCH2Cl2/MeOH (4:1) as eluent.

With the rapid development of chemical substances, we look forward to future research findings about 65996-58-9.

Reference:
Article; Rodrigues, Marili V.N.; Barbosa, Alexandre F.; Da Silva, Julia F.; Dos Santos, Deborah A.; Vanzolini, Kenia L.; De Moraes, Marcela C.; Correa, Arlene G.; Cass, Quezia B.; Bioorganic and Medicinal Chemistry; vol. 24; 2; (2016); p. 226 – 231;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 304693-66-1, 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. 304693-66-1, name is 2-(Trifluoromethyl)pyrimidine-5-carbaldehyde, molecular formula is C6H3F3N2O, 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.

Step B: (1S,3S,4R)-3-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-4-methyl-N-((2-(trifluoromethyl)pyrimidin-5-yl)methyl)cyclopentylamine To a solution of ethyl 2-(trifluoromethyl)pyrimidine-5-carboxylate (0.750 g, 2.73 mmol) in toluene (13.6 mL) at about -78 C. was added DIBAL-H (1M in cyclohexane, 3.30 mL, 3.30 mmol) over about 15 min and the reaction was left stirring at about -78 C. for about 1 h. The reaction was quenched with the slow addition of 2N aqueous HCl (13.6 mL) and the reaction was warmed to ambient temperature. The reaction mixture was extracted with ether (3*15 mL) and the combined organics were dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure to give crude 2-(trifluoromethyl)pyrimidine-5-carbaldehyde. To a mixture of (1S,3S,4R)-3-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-4-methylcyclopentylamine (0.112 g, 0.437 mmol, Example No.1, Step D) and 2-(trifluoromethyl)pyrimidine-5-carbaldehyde (0.100 g, 0.568 mmol) in DCE (1.00 mL) and MeOH (1.00 mL) was added acetic acid (0.038 mL, 0.655 mmol) and sodium triacetoxyborohydride (0.139 g, 0.655 mmol). The reaction was left stirring at ambient temperature for about 3 h. The reaction was concentrated under reduced pressure and the residue was taken up in DCM and saturated aqueous NaHCO3 (10 mL each). The layers were separated and the aqueous phase was extracted with DCM (2*10 mL) and EtOAc (10 mL). The combined organics were dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The crude material was purified by silica gel chromatography eluting with 0-10% MeOH in DCM to give (1S,3S,4R)-3-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-4-methyl-N-((2-(trifluoromethyl)pyrimidin-5-yl)methyl)cyclopentylamine (0.035 g, 19%) as an off-white solid; LC/MS (Table 1, Method a) Rt=1.28 min; MS m/z: 416 (M+H)+. Jak3 IC50=C

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 304693-66-1, 2-(Trifluoromethyl)pyrimidine-5-carbaldehyde.

Reference:
Patent; ABBVIE INC.; Wishart, Neil; Bonafoux, Dominique F.; Frank, Kristine E.; Hobson, Adrian D.; Konopacki, Donald B.; Martinez, Gloria Y.; Wang, Lu; US2013/72470; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 3993-78-0, 2-Amino-4-chloropyrimidine, 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, Product Details of 3993-78-0, blongs to pyrimidines compound. Product Details of 3993-78-0

4-(lH-indol-l-yl)pyrimidin-2-amine (15a). A mixture of 2-amino-4-chloropyrimidine (0.206g, 1.590mmol), indole (0.372g, 3.180mmol) and Cs2C03 (1.550g, 4.77 mmol) in anhydrous DMF (1.6 ml) was stirred in a Biotage microwave reactor for lh at 110 C. After cooling to room temperature, the reaction mixture diluted with water (5ml) and extracted with ethyl acetate (2 x 10ml). The combined organic extracts were dried over Na2S04 and the solvent removed under reduced pressure. Chromatography on silica gel using the FlashM aster 3 purification station (AcOEt/Hexane) afforded 15a (0.125 g, 0.593 mmol, 37%) as an off-white solid. 1H NMR (400 MHz, OMSO-d6) delta 8.78 (d, 1H, J = 8.28 Hz), 8.23 (d, J = 5.64 Hz, 1H), 8.03 (d, J = 3.64 Hz, 1H), 7.59 (d, J = 7.76 Hz, 1H), 7.27-7.22 (m, 1H), 7.17 (t, J = 7.36 Hz, 1H), 6.93 (d, J = 5.92 Hz, 1H), (bs, 2H), 6.74 (d, J = 3.60 Hz, 1H); HRMS (ESI-ve) calculated for Ci2Hn 4 (M+H)+ 211.0978, found 211.0979.

The synthetic route of 3993-78-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER & RESEARCH INSTITUTE INC.; LAWRENCE, Nicholas, J.; SEBTI, Said, M.; PIREDDU, Roberta; WO2012/135697; (2012); A2;,
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. 24391-41-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile. A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

A mixture of 1e (30 mg, 0.095 mmol), 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5- carbonitrile (22 mg, 0.128 mmol) and TEA (0.05 ml, 0.360 mmol) in n-BuOH (3 mL) was stirred at reflux for 1.5 h. The reaction mixture was concentrated and purified by flash column chromatography eluting with MeOH/DCM to afford Compound 1 as a white solid (29 mg, yield: 64%). MS (m/z): 422.6 (M+H)+. 1H NMR (400 MHz, DMSO-d6) delta: 12.81 (s, 1H), 8.27-8.26 (m, 2H), 7.72-7.68 (m, 1H) , 7.64-7.41 (m, 5H), 6.88 (dd, J= 4.3, 1.7 Hz, 1H), 6.47 (dd, J = 4.3, 2.7 Hz, 1H), 4.72-4.65 (m, 1H), 4.12-4.06 (m, 1H), 3.96-3.89 (m, 1H), 2.35-2.15 (m, 2H) 2.06-1.83 (m, 2H).

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, 24391-41-1, 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-guo; DAI, Guangxiu; XIAO, Kun; JIA, Hong; ZHANG, Zhulin; VENABLE, Jennifer Diane; BEMBENEK, Scott Damian; CHAI, Wenying; WO2014/15830; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 50270-27-4, 2,4,6-Trichloropyrimidine-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, 50270-27-4, blongs to pyrimidines compound. HPLC of Formula: C5HCl3N2O

To a solution of 2,4,6-trichloro-pyrimidine-5-carbaldehyde (2.5 g, 11.6 mmol) in EtOH (40 mL) cooled to -78 C was added N-benzyl-4-piperidinzyl-hydrazine dihydrochloride (3.3 g, 11.6 mmol) and TEA (5 mL). The mixture was stirred for 30 min at -78 C then 2 hr at 0 C. The solution was concentrated in vacuo without heating. To the reduced volume solution EtOAc and a sat NaHCO3 solution was added and the solution filtered over Celite.(TM). and separated. The organic layer was dried (MgSO4) and concentrated in vacuo without heating. Filtration over a small silica gel plug (EtOAc) and concentration afforded the desired product as a yellow solid (3 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,50270-27-4, its application will become more common.

Reference:
Patent; Wyeth; US2009/98086; (2009); 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. 696-07-1, name is 5-Iodouracil, the common compound, a new synthetic route is introduced below. COA of Formula: C4H3IN2O2

A suspension of 5-iodouracil (1.8g, 7.54mmol) in dry acetonitrile (15mL) was treated with N,O-bis(trimethylsilyl) acetamide (4.62mL, 18.87mmol) and left to stir until the solution became clear. A solution of a mixture of isoxazolidines 12, 13 (2.6g, 6.29mmol) in dry acetonitrile (15mL) and trimethylsilyl triflate (0.22mL, 1.25mmol) was then added, and the reaction mixture was stirred at room temperature overnight. After this time, the solution was carefully neutralized by the addition of 5% aqueous sodium hydrogen carbonate and then concentrated in vacuo. After addition of dichloromethane (20mL), the organic phase was separated, washed with water (2×10mL), dried with sodium sulfate, filtered, and concentrated. The 1H NMR spectrum of the crude reaction mixture showed the presence of beta-anomers (cis) as nearly exclusive adducts, whereas the alpha-anomers were present only in trace amounts. The residue was purified by MPLC on a silica gel column (cyclohexane/ethyl acetate, 7:3) to afford 14. Yellow oil, 3.65g, 90% yield. 1H NMR (500MHz, CDCl3): delta=8.90 (br s, 1H), 8.25 (s, 1H), 7.65 (dd, J=7.9, 1.4Hz, 4H), 7.49-7.37 (m, 6H), 6.01 (dd, J=7.5, 3.4Hz, 1H), 3.71 (dd, J=4.7, 2.0Hz, 2H), 2.96 (dt, J=13.7, 7.8Hz, 2H), 2.90-2.84 (m, 1H), 2.82 (s, 3H), 2.25-2.09 (m, 1H), 1.05 (s, 9H). 13C NMR (126MHz, CDCl3): delta=160.23, 150.15, 145.33, 135.69, 132.83, 130.10, 128.02, 83.84, 69.35, 67.65, 63.08, 44.85, 41.82, 26.95, 19.31. Anal. calcd for C25H30IN3O4Si: C, 50.76; H, 5.11; N, 7.10; found: C, 50.73; H, 5.12; N, 7.11.

The synthetic route of 696-07-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Romeo, Roberto; Giofre, Salvatore V.; Garozzo, Adriana; Bisignano, Benedetta; Corsaro, Antonino; Chiacchio, Maria A.; Bioorganic and Medicinal Chemistry; vol. 21; 18; (2013); p. 5688 – 5693;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia