Pyrimidines

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.37972-24-0, name is 2-Ethynylpyrimidine, molecular formula is C6H4N2, molecular weight is 104.11, as common compound, the synthetic route is as follows.Application In Synthesis of 2-Ethynylpyrimidine

To a solution of 235(100mg, 0.272rnrnoi) and 4(56.6mg, 0543mmo1) in 2OrnL of Et3N was added Pd(PPh3)2C12 (9.53mg, 0.0 i4mmol) and Cui (5.17mg, 0.O27mmol). The mixture was protected with N2 atmosphere, then was heated at 70¡ãC for 4 hours. TLC analysis showedcomplete conversion of starting material to major product. The reaction mixture was then concentrated in vacuo. The crude product was purified by Prep-HPLC to give the target product Compound 133(24mg, yield: 25.7percent).LCMS: m/z 345 (M+HY;111 NMR (400 MHz, CDCI3): oe 8.76 (d, J= 4.0 Hz, 2H), 754 . 7.52. (m, 211), 7.35 7.32 (m,211), 7 25 (t J 4 6 Hz 1TI) 6 52 (d, / 0 4 lTz 111), 2 P (d, 1 0 4 Hz, 311)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,37972-24-0, 2-Ethynylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; HUA MEDICINE (SHANGHAI) LTD.; CHEN, Li; JIN, Xiaowei; (176 pag.)WO2017/117708; (2017); A1;,
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Electric Literature of 105806-13-1, 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 105806-13-1, name is 4,6-Dichloro-5-fluoro-2-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Part C: A mixture of 4,6-dichloro-5-fluoro-2-methylpyrimidine (1.55 g, 8.56 mmol), ammonium hydroxide (35%, 10.0 mL, 257 mmol), and MeOH (1.00 mL) was heated, in a sealed tube, at 70 C. for 2 h. The reaction mixture was cooled to RT, and a precipitate was formed. The reaction mixture was diluted with water (ca. 10 mL) and was stirred 30 min. The solids were collected by suction filtration, washed with water and air-dried to give 4-amino-6-chloro-5-fluoro-2-methylpyrimidine (845 mg, 61%) as a tan solid. LCMS (m/z): 162,164 (M+H)+

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 105806-13-1, 4,6-Dichloro-5-fluoro-2-methylpyrimidine.

Reference:
Patent; ICAGEN, INC.; US2007/197523; (2007); A1;,
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Adding a certain compound to certain chemical reactions, such as: 504-17-6, 4,6-Dihydroxy-2-mercaptopyrimidine, 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, Computed Properties of C4H4N2O2S, blongs to pyrimidines compound. Computed Properties of C4H4N2O2S

General procedure: To a mixture of ethyl acetoacetate (1 mmol, 0.13 g) and hydrazine hydrate (1 mmol, 0.05 g) in magnetized water was added an aldehyde (1 mmol) and thiobarbituric acid (1mmol, 0.144 g). The reaction mixture was stirred at 50 C,and the reaction progress was monitored by TLC using chloroform as the eluent. After completion of the reaction, the precipitate formed was filtered and purified by recrystallization from ethanol to afford the desired product

At the same time, in my other blogs, there are other synthetic methods of this type of compound,504-17-6, 4,6-Dihydroxy-2-mercaptopyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Bakherad, Mohammad; Doosti, Rahele; Keivanloo, Ali; Gholizadeh, Mostafa; Amin, Amir H.; Letters in Organic Chemistry; vol. 14; 7; (2017); p. 510 – 516;,
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Application of 1337532-51-0 ,Some common heterocyclic compound, 1337532-51-0, molecular formula is C7H7BrN4, 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 5-bromo-7-methyl-7/-/-pyrrolo[2,3-c]pyrimidin-4-amine (0.31 g, 1.37 mmol), 1- [4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl]-3-[3-(trifluoromethyl)phenyl]-2- pyrrolidinone (0.59 g, 1.37 mmol), Pd2(dba)3 (63 mg, 0.07 mmol) and K3P04 (0.63 g, 2.74 mmol) in 10 mL of dioxane and 3.3 mL of water in a 20 mL microwave vial was bubbled with argon for 10 min, and then tri-(t-butyl)phosphonium tetrafluoroborate (40 mg, 0.14 mmol) was added. The mixture was capped and heated in a metal matrix block at 100 C. After 18 h, LCMS showed conversion complete. The mixture was filtered. The filtrate was concentrated in vacuo. The residue was taken up in water (30 mL) to give a suspension, which was filtered. The solid cake was washed with water and ether. The cake was dried under house vacuum, dissolved in 10% MeOH in DCM. The organic was dried over Na2S04, filtered, and concentrated in vacuo. The residue was dissolved in 10% MeOH in DCM and was absorbed onto a dryload silica gel cartridge. Purification was performed on a 115 g silica gel cartridge using gradient elution of 1 % A to 60% A in CHCI3 (A was a mixture of 3200/800/80 CHCI3/MeOH/NH4OH). The desired product eluted from 25-30% A. The combined fractions containing pure product were concentrated in vacuo. The residue was dissolved in 10% MeOH in CHCI3 and filtered. The filtrate was concentrated in vacuo and the residue was dissolved in 10% MeOH in DCM (12 mL), to which was added MTBE (15 mL). Solids slowly formed, resulting in a suspension. This mixture was concentrated in vacuo to reduce to half volume, followed by addition of another 15 mL of MTBE. The suspension was filtered. The cake was washed with MTBE (2 x 5 mL) and hexane (2 x 4 mL), dried under vacuum at 65 C for 20 h to afford 1-4-(4-amino-7-methyl- 7/-/-pyrrolo[2,3-c]pyrimidin-5-yl)phenyl)-3-(2,5-difluorophenyl)pyrrolidin-2-one (449 mg) as an off-white solid. LCMS (ES) m/z = 452 [M+H]+. H NMR (400 MHz, DMSOd6) delta ppm 2.22 – 2.35 (m, 1 H), 2.58 – 2.71 (m, 1 H), 3.75 (s, 3 H), 4.00 (dd, J=8.8, 5.3 Hz, 2 H), 4.17 (t, J=9.6 Hz, 1 H), 5.97 – 6.18 (br s, 1.2 H), 7.32 (s, 1 H), 7.49 (d, J=8.6 Hz, 2 H), 7.60 – 7.70 (m, 3 H), 7.73 (s, 1 H), 7.83 (d, J=8.8 Hz, 2 H), 8.16 (s, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1337532-51-0, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AXTEN, Jeffrey M.; MEDINA, Jesus Raul; WO2015/136463; (2015); A1;,
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Reference of 36847-10-6, 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. 36847-10-6, name is 4,6-Dibromopyrimidine. A new synthetic method of this compound is introduced below.

To CH2Cl2 solution (20 mL) containing pmbNOH (25 mg; 0.10 mmol) was added excess Ag2O (ca. 1 mmol) with being stirred at room temperature. The mixture was stirred for further 20 min. Filtration followed by concentration under reduced pressure gave an oily product (pmbNO). The IR spectrum supports the absence of the hydroxyl group. IR (neat, ATR) 729, 860, 985, 1191, 1223, 1246, 1344, 1365, 1444, 1481, 1555, 2935, 2984 cm-1. The MS spectrum indicates the loss of two H atoms from the precursor. MS (ESI+-TOF in MeOH) m/z 275.16 [(M+Na)+]. At this stage, pmbNO could be characterized by means of ESR spectroscopy and SQUID magnetometry (see the main text). The resultant pmbNO was dissolved again in CH2Cl2 (20 mL) and covered with a hexane solution (5 mL) of anhydrous [Cu(hfac)2] (95 mg). After slow diffusion of the solutions, reddish brown plates of [Cu3(pmbNO)2(hfac)4]¡¤(C6H14) (10 mg; 12%) were grown and separated on a filter.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,36847-10-6, 4,6-Dibromopyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Homma, Yuta; Okazawa, Atsushi; Ishida, Takayuki; Tetrahedron Letters; vol. 54; 24; (2013); p. 3120 – 3123;,
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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. 155-90-8, name is 2-Amino-4-methoxypyrimidine, molecular formula is C5H7N3O, 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. Product Details of 155-90-8

Method 14; Synthesis of 5-bromo-4-methoxypyrimidine-2-ylamine; [0255] To a solution of 4-methoxypyrimidine-2-ylamine (1.84 g, 14.7 mmol) in chloroform (600 mL) was added N-bromosuccinimide (2.62 g, 14.7 mmol). After stirring in the dark for 5 hours, the solution was added to CH2Cl2 (200 mL) and IN NaOH(10O mL). Upon mixing, the layers were separated and the organic layer was washed with NaCl(sat) (10O mL), dried over Na2SO4, filtered and concentrated yielding 2.88 g(96%) of 5-bromo-4-methoxypyrimidine-2-ylamine. LCMS (m/z): 204/206 (MH+). 1H NMR (CDCl3): delta 8.10 (s, IH), 4.93 (bs, 2H), 3.96 (s, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 155-90-8.

Reference:
Patent; NOVARTIS VACCINES AND DIAGNOSTICS, INC.; WO2008/98058; (2008); A1;,
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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. 1005-38-5, name is 4-Amino-6-chloro-2-(methylthio)pyrimidine, the common compound, a new synthetic route is introduced below. COA of Formula: C5H6ClN3S

[00549] To a stirred solution of 6-chloro-2-(methylsulfanyL)pyrimidin-4-amine (1.5 g, 8.54 mmol) in dioxane (4 mL) was added chloroacetaldehyde (50%, 1.63 mL, 12.8 mmol) and stirred at 95 C overnight. The reaction mixture was cooled in an ice bath and the resulting precipitate filtered and washed with dioxane to afford the title compound (1.41 g, 70%) as a colourless powder. [00550] Method A: LC-MS m/z = 199.8 [M + H]+; RT = 0.93 min

The synthetic route of 1005-38-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; QUARTET MEDICINE, INC.; ECOLE POLYTECHNIQUE FEDERALE DE LAUSANNE (EPFL); TEBBE, Mark, Joseph; ATTON, Holly, Victoria; AVERY, Craig; BROMIDGE, Steven, Mark; KERRY, Mark; KOTEY, Adrian, Kotei; MONCK, Nathaniel, J.; MENICONI, Mirco; RIDGILL, Mark, Peter; TYE, Heather; SAIAH, Eddine; JOHNSSON, Kai, Peter; GORSKA, Katarzyna, Irena; PENG, Hairuo; MCCALL, John, Michael; (356 pag.)WO2017/59191; (2017); A1;,
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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. 5734-66-7, name is 2-Amino-6-ethylpyrimidin-4-ol. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

A. 2-Amino-5-bromo-6-ethyl-4-pyrimidinol By bromination of 6-ethyl-isocytosine with N-bromosuccinimide To a faintly warm solution of 1.112 g. (8.0 millimoles) of 6-ethyl-isocytosine in 16 ml. of glacial acetic acid is added 1.424 g. (8.0 millimoles) of N-bromosuccinimide. The reaction flask is closed with a drying tube, and the mixture heated briefly on a steam bath, with occasional swirling, until solution is complete. The solution is heated on a steam bath for 1 hour, then allowed to cool spontaneously. The cooled solution is seeded with crystals from an earlier run and kept at ambient temperature for several days. The resulting crystals are collected, washed first with cool glacial acetic acid then with anhydrous ether. The material is dried, first in air then in vacuo at 76C. for several hours. The crude material, 960 mg., is crystallized from about 20 ml. of 50% aqueous acetic acid, using decolorizing charcoal. The product is collected, washed successively with cold 50% aqueous acetic acid, cold 95% ethanol and anhydrous ether. The pure material, after brief airdrying, is dried in vacuo at ca. 80C. There is thus obtained 660 mg. of 2-amino-5-bromo-6-ethyl-4-pyrimidinol which melts at 225 to 225.5 centigrade, has a lambdamax0.1N NaOH 230.5 nm. (epsilon8,200); 283 nm. (epsilon7,200) and the infrared absorption below. Nh/oh, 3380, 3320, 3130, 2720; c=o/c=n/c=c, 1675, 1640, 1610, 1565; c–o/c–n other, 1340, 1310, 1215, 1060, 1005 cm-1. Analysis Calcd. for: C6 H8 BrN3 O: C, 33.05; H, 3.17; Br, 36.65; N, 19.27.Found: C, 32.98; H, 3.63; Br, 36.75; N, 18.81.

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, 5734-66-7, 2-Amino-6-ethylpyrimidin-4-ol.

Reference:
Patent; The Upjohn Company; US3956302; (1976); A;,
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Pyrimidine – Wikipedia

Reference of 14160-93-1, 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. 14160-93-1, name is 4-Amino-6-chloropyrimidine-5-carbaldehyde. A new synthetic method of this compound is introduced below.

To a mixture of trimethoxybenzylamine (469 mg, 2.38 mmol, 1.0 equiv., HCl salt free based prior to use), 4 angstrom molecular sieves (290 mg), and aldehyde 15.2 (375 mg, 2.38 mmol, 1.0 equiv.) in dichloromethane (5 mL) was added acetic acid (0.14 mL, 2.43 mmol, 1.02 equiv.). After stirring for 3 hr at RT, sodium triacetoxyborohydride (757 mg, 3.57 mmol, 1.5 equiv.) was added and the reaction mixture was stirred at RT for 21.5 hr. The reaction mixture was diluted with dichloromethane (20 mL) and aqueous saturated NaHCO3 (20 mL). The aqueous layer was extracted with dichloromethane (4¡Á20 mL), and the combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The resultant crude residue and Boc2O (524 mg, 2.38 mmol, 1 equiv.) were dissolved in THF (10 mL), and pyridine (0.59 mL, 5.95 mmol, 2.5 equiv.) was added. After stirring at RT for 16.5 hr, the reaction mixture was diluted with water (25 mL), EtOAc (25 mL), and 1 N aqueous HCl (25 mL). The aqueous layer was extracted with EtOAc (4¡Á30 mL). The combined organic extracts were washed with water (50 mL), 1 N aqueous HCl (50 mL), and brine (50 mL), dried over anhydrous sodium sulfate, and concentrated. Purification by flash column chromatography (50-60-66% EtOAc/hexanes) afforded compound 15.3 (403 mg, 39% over 2 steps) as a beige foam. LCMS: m/z: 439 [M+1]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14160-93-1, 4-Amino-6-chloropyrimidine-5-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Sunesis Pharmaceuticals, Inc.; US2009/36419; (2009); 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.22536-66-9, name is 2-Chloropyrimidine-4-carboxamide, molecular formula is C5H4ClN3O, molecular weight is 157.5578, as common compound, the synthetic route is as follows.HPLC of Formula: C5H4ClN3O

To a 5 mL vial containing a stir bar, 3-(2-aminopyrimidin-5-yl)-6-cyclobutyl-2-fluorophenol (80 mg, 0.31 mmol) and 2-chloropyrimidine (41 mg, 0.34 mmol) were added Cs2CO3 (203 mg, 0.62 mmol) and DMSO (0.8 mL). The resultant mixture was stirred at 120 Celsius for approximately 1 hour via microwave irradiation. The reaction mixture was cooled to room temperature before passing the mixture through a syringe filter and subjecting the filtrate to FCC to afford the title compound (81 mg, 78%). The title compound was prepared using conditions similar to those described in Example 160 heating at 80 Celsius via microwave radiation for 2 hours and using 2-chloropyrimidine-4-carboxamide. MS (ESI): mass calcd. for C19H17FN6O2, 380.14; m/z found, 381.0 [M+H]+. 1H NMR (400 MHz, DMSO-d6) delta 8.81 (d, J=4.9, 1H), 8.44 (s, 2H), 8.21 (s, 1H), 7.98 (s, 1H), 7.77 (d, J=4.9, 1H), 7.52-7.42 (m, 1H), 7.30 (d, J=8.2, 1H), 6.89 (s, 2H), 3.63-3.51 (m, 1H), 2.15-2.00 (m, 4H), 1.99-1.84 (m, 1H), 1.81-1.68 (m, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22536-66-9, 2-Chloropyrimidine-4-carboxamide, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Eccles, Wendy; Fitzgerald, Anne E.; Hack, Michael D.; Hawryluk, Natalie A.; Jones, William M.; Keith, John M.; Krawczuk, Paul; Lebsack, Alec D.; Liu, Jing; Mani, Neelakandha S.; McClure, Kelly J.; Meduna, Steven P.; Rosen, Mark D.; US2014/221310; (2014); A1;,
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