Pyrimidines

Related Products of 25940-35-6, 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 25940-35-6, name is Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of [1-(5-amino-2,2-dimethyl-3H-benzofuran-6-yl)-4-piperidyl]methyl diethyl phosphate (79 mg, 0.14 mmol), pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (27 mg, 0.17 mmol), 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (78 mg, 0.21 mmol) and diisopropylethylamine (53 mg, 0.41 mmol) in N,N-dimethylformamide (5 mL) was stirred at 20 C for 1h. The mixture was purified by preparative HPLC (Xbridge 21.2*250mm c18, 10um; A: acetonitrile 25-55%; B: 10 mM ammonium bicarbonate in water) to afford [1-[2,2-dimethyl-5-(pyrazolo[1,5-a]pyrimidine-3-carbonylamino)-3H-benzofuran-6-yl]-4- piperidyl]methyl diethyl phosphate (7 mg, 9%) as yellow solid.1H NMR (400 MHz, CDCl3): delta 10.51 (s, 1H), 8.85 (dd, J = 1.6, 4.0 Hz, 1H), 8.79-8.76 (m, 2H), 8.44 (s, 1H), 7.10 (dd, J = 1.6, 7.2 Hz, 1H), 6.63 (s, 1H), 4.14 (q, J=7.2 Hz, 4H), 4.01-4.00 (m, 2H), 3.11 (d, J = 11.6 Hz, 2H), 3.03 (s, 2H), 2.69-2.64 (m, 2H), 1.87-1.77 (m, 5H), 1.48 (s, 6H), 1.35 (t, J = 6.8 Hz, 6H). MS (ESI): m/z = 558.3 [M+1]+.

According to the analysis of related databases, 25940-35-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BRYAN, Marian, C.; GOBBI, Alberto; KIEFER, James, Richard, Jr.; KOLESNIKOV, Aleksandr; OLIVERO, Alan, G.; DROBNICK, Joy; LIANG, Jun; RAJAPAKSA, Naomi; (846 pag.)WO2017/108723; (2017); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 153435-63-3, 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. 153435-63-3, name is 2-(Tributylstannyl)pyrimidine. A new synthetic method of this compound is introduced below.

Description 28: methyl 6-methyl-3-(2-pyrimidinyl)-2-pyridinecarboxylate (D28); To a suspension of methyl 3-iodo-6-methyl-2-pyridinecarboxylate D27 (300 mg), CsF (329 mg, 2.166 mmol) and Pd(Ph3P)4 (50.0 mg, 0.043 mmol) in DMF (10 ml) stirred under nitrogen at room temperature, was added 2-(tributylstannanyl)pyrimidine (480 mg, 1.299 mmol). The reaction mixture was stirred at 130 0C for 30 minutes in a microwave Personal Chemistry. The reaction mixture was partitioned between EtOAc and aqueous NaHCO3 saturated solution; the combined organic phases were dried to give the crude product, which was purified by silica gel chromatography (SNAP KP-NH 55 g; Cy/EtOAc from 100:0 to 70:30). Collected fractions were evaporated to obtain the title compound D28 (101 mg) as white solid. UPLC (Basic GEN_QC): rt = 0.56 minutes, peak observed: 230 (M+l). C12H11N3O2 requires 229. 1H NMR (400 MHz, DMSO-J6) delta ppm 8.92 (d, 2 H), 8.49 (d, 1 H), 7.44 – 7.63 (m, 2 H), 3.75 (s, 3 H), 2.57 (s, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153435-63-3, 2-(Tributylstannyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; AMANTINI, David; DI FABIO, Romano; WO2010/122151; (2010); A1;,
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Pyrimidine – Wikipedia

Reference of 932-52-5, 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.932-52-5, name is 5-Aminopyrimidine-2,4(1H,3H)-dione, molecular formula is C4H5N3O2, molecular weight is 127.1014, as common compound, the synthetic route is as follows.

Intermediate 1.1; Dimethyl (2E)-2-[(2.4-dioxo-1.2.3.4-tetrahvdro-5-pyriimdinvD-aminol-2-butenedioate (Scheme 7); To a suspension of 5-aminouracil (B)(4.0 g; 31.5 mmol; 1 eq.) in MeOH (120.00 mL) was added dimethyl acetylenedicarboxylate (C) (5.0 g; 35.2 mmol; 1.1 eq.). The suspension was stirred at room temperature for 46h. The reaction was monitored by NMR. The solid was filtered to afford dimethyl (2E)-2-[(2,4-dioxo-l,2,3,4-tetrahydro-5-pyrimidinyl)amino]-2-butenedioate (8.0 g, 95%) (Intermediate 1.1).Amount: 8.0 g; Yield: 95%; Formula: Ci0HiiO6N3; HPLC Purity: 95% ; HPLC (HzO TFA Q.1%- ACN TFA Q.05%): Rt (min); Area % = 1.37; 93.61: 1H NMR (DMSO-d6) 8 3.64 (s, 3H), 3.66 (s, 3H), 5.21 (s, 1H), 7.42 (s, 1H), 9.07 (s, 1H), 10.86 (br, 1H), 11.31 (br, 1H); LC-MS:M/ZESI: Rt (min) 0.85 ; 210, 238, 270 (M+l) ; 208, 236, 268 (M-l).

Statistics shows that 932-52-5 is playing an increasingly important role. we look forward to future research findings about 5-Aminopyrimidine-2,4(1H,3H)-dione.

Reference:
Patent; APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.; WO2006/24666; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 24867-26-3, 2,4-Diamino-6-piperidinopyrimidine, 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, Quality Control of 2,4-Diamino-6-piperidinopyrimidine, blongs to pyrimidines compound. Quality Control of 2,4-Diamino-6-piperidinopyrimidine

EXAMPLE 9 Preparation of di-n-propyl 6-piperidinopyrimidine-2,4-dioxamate: 2,4-Diamino-6-piperidinopyrimidine (5.8 g) is dissolved in anhydrous pyridine (80 ml) and thereto is added dropwise n-propyloxalyl chloride (9.8 g) at room temperature, and the mixture is stirred at room temperature for 2 hours. The precipitated pyridine hydrochloride is filtered off, and the mother liquor is concentrated under reduced pressure. The remaining oily residue is dissolved in chloroform and the mixture is washed with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. The solvent is distilled off, and the resulting oily residue is dissolved in ethyl acetate and thereto is added ether. the precipitated solid is separated by filtration and recrystallized from ethanol to give title compound (6.3 g) having the following physical properties. m.p. 97.4-101.4 C. IR (KBr) nu: 3450, 3260, 2980, 2950, 2870, 1740, 1725, 1690, 1620, 1540, 1490, 1450, 1400, 1385, 1360, 1345, 1300, 1285, 1270, 1240, 1215, 1195, 1180, 1060, 1040, 1025, 985, 820 cm-1. NMR (DMSO-d6) delta: 10.88 (bs, 1H), 10.15 (bs, 1H), 6.95 (s, 1H), 4.18 (t, 2H), 4.12 (t, 2H), 3.65-3.20 (4H), 1.90-1.10 (10H), 0.94 (t, 3H), 0.84 (t, 3H) Elementary analysis: Calcd.: C, 54.15; H, 6.46; N, 16.62 (%). Found: C, 54.36; H, 6.30; N, 16.77 (%).

The synthetic route of 24867-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Toyo Boseki Kabushiki Kaisha; US4729995; (1988); A;,
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Pyrimidine – Wikipedia

Reference of 939986-65-9, 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. 939986-65-9, name is 6-Chloropyrimidine-4-carbonitrile, molecular formula is C5H2ClN3, 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.

Compound 8 (800 mg, crude) was added to a DMF (8 ml) solution, then DBU (912 mg, 6 mmol) was added, and compound 9 (6-chloro-4-pyrimidinecarbonitrile) (552 mg, 4 mmol) was added. The reaction was performed at 80 C. After 6 hours, TLC showed that a large amount of the starting compound 8 remained, and then compound 9 (6-chloro-4-pyrimidinecarbonitrile) (276 mg, 2 mmol) was added. The reaction temperature was raised to 100 C for 12 hours, and the reaction solution was poured into Water was extracted with dichloromethane. The organic phases were combined, washed with water, washed with saturated sodium chloride, and dried over anhydrous sodium sulfate. The residue was spin-dried and passed through a silica gel column (mobile phase: PE: EA = 3: 1) to obtain a crude product. Further, the compound I (also referred to as “compound NHWD-1062”) is prepared through a high-performance liquid phase.MS (ESI) m / z: 364.4 (M + H +). 1HNMR (400MHz, CDCl3) 8.6 (s, 1H), 7.2-7.4 (m, 5H), 6.8 (s, 1H), 5.4 (m, 1H) , 4.3 (m, 2H), 3.9 (m, 1H), 3.1-3.2 (m, 3H), 2.8 (m, 1H), 2.4 (m, 1H), 2.1 (m, 1H), 1.7-1.9 (m , 3H), 1.3 (m, 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 939986-65-9, 6-Chloropyrimidine-4-carbonitrile.

Reference:
Patent; Ningbo Wenda Pharmaceutical Technology Co., Ltd.; Wang Nenghui; (20 pag.)CN110872285; (2020); A;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 591-55-9, 5-Aminopyrimidine, 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, 591-55-9, blongs to pyrimidines compound. Computed Properties of C4H5N3

Example 75(1R,2S)-2-(4-(cyclohexyl(4,4,4-trifluorobutyl)amino)-3-(3-pyrimidine-5-yl)ureido)phenyl)cyclopropanecarboxylic acid 75A. (1R,2S)-ethyl 2-(4-(cyclohexyl(4,4,4-trifluorobutyl)amino)-3-(3- (pyrimidin-5-yl)ureido)phenyl)cyclopropanecarboxylateIn a one-dram sample vial with stirbar was placed 73F (53.3 mg, 0.129 mmol) and THF (1988 tl). To this stirred solution was added 4-nitrophenyl carbonochloridate (27.3 mg, 0.136 mmol). The reaction was stirred at rt for 30 mm. Pyrimidin-5-amine (36.9 mg, 0.388 mmol) and triethylamine (54.0 tl, 0.388 mmol) were added and the reaction was heated at 50 C. After 17 h, the reaction was cooled to rt, then dried under a stream ofnitrogen. The concentrate was diluted with water and extracted with EtOAc (3x). The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and concentrated under a reduced pressure to give 75A. The crude product was used directly in the subsequent procedure. Anal. Calc?d for C27H34F3N503 533.26, found [M+H] 534.4, T = 2.15 mm (Method E).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,591-55-9, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; HUANG, Audris; CHEN, Bin; CHEN, Libing; SEITZ, Steven P.; HART, Amy C.; MARKWALDER, Jay A.; WO2014/150677; (2014); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1722-12-9, 2-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, COA of Formula: C4H3ClN2, blongs to pyrimidines compound. COA of Formula: C4H3ClN2

To a solution of methyl 5-methyl-2-(tetramethyl-1 ,3,2-dioxaborolan-2-yl)benzoate (p59, 1 .51 g, 5.5 mmol) in 2-MeTHF (20 mL), 2-chloropyrimidine (0.756 g, 6.6 mmol) and Sodium carbonate (1 .75 g, 16.5 mmol) were added. To this stirring suspension water (4 mL) was added. The thick slurry was degassed with nitrogen for 40 minutes, then PdCl2(dppf)-CH2Cl2 adduct (0.163 g, 0.2 mmol) was added. The internal temperature was set to 74C and the mixture stirred for 16 hrs. The reaction was gone to completion therefore it was cooled to room temperature and treated with water (6 mL) and diethyl ether (12 mL) while maintaining stirring for 10 minutes. This solution was filtered washing with further diethyl ether (12 mL) and water (8 mL) then 12 mL of diethyl ether more. The layers was separated, organic one was dried and concentrated and the crude purified by FC on silica gel (eluent: Cy/EtoAc 7/3) affording methyl 5-methyl-2-(pyrimidin-2- yl)benzoate (p60, 231 mg, y= 18%). MS (/T7/z): 228.0 [MH]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1722-12-9, 2-Chloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; CHRONOS THERAPEUTICS LIMITED; MICHELI, Fabrizio; BERTANI, Barbara; GIBSON, Karl Richard; DI FABIO, Romano; RAVEGLIA, Luca; ZANALETTI, Riccardo; CREMONESI, Susanna; POZZAN, Alfonso; SEMERARO, Teresa; TARSI, Luca; LUKER, Timothy Jon; (275 pag.)WO2019/43407; (2019); A1;,
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Pyrimidine – Wikipedia

Reference of 5018-38-2 , The common heterocyclic compound, 5018-38-2, name is 4,6-Dichloro-5-methoxypyrimidine, molecular formula is C5H4Cl2N2O, 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 solution of 4,6-dichloro-5-methoxy-pyrimidine (5.62 g, 27.9 mmol) and 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (5.02 g, 27.9 mmol) in 200 mL THF was chilled to 0 C. A 1.0 M solution of potassium t-butoxide (30.7 mL, 30.7 mmol) was added drop-wise with stirring and the resulting mixture then was allowed to stir at 0 C. for one hour. Saturated ammonium chloride (100 mL) was added and the solution extracted with ethyl acetate. The organic phase was washed with brine and dried with magnesium sulfate, solvent removed to yield 9.10 g (94.8% yield). 1HNMR (CDCl3, 400 MHz) delta 1.48 (s, 2H), 1.79-1.83 (m, 2H), 1.99-2.04 (m, 2H), 3.33-3.39 (m, 2H), 3.72-3.77 (m, 2H), 3.91 (s, 3H), 5.30-5.38 (m, 1H), 8.26 (s, 1H). Exact mass calculated for C15H22ClN3O4: 343.13, found: 344.3 (MH+).

The synthetic route of 5018-38-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jones, Robert M.; Lehmann, Juerg; Wong, Amy Siu-Ting; Hurst, David; Shin, Young-Jun; US2006/155128; (2006); A1;,
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Pyrimidine – Wikipedia

Application of 5750-76-5, 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. 5750-76-5, name is 2,4,5-Trichloropyrimidine. A new synthetic method of this compound is introduced below.

To a 250 mL round bottom flask equipped with a stir bar was added 2,4,5-trichloro- pyrimidine (1 g), and diethyl ether (15 mL). The mixture was cooled to 0C in an ice bath and then 1 equivalent of sodium methoxide in methanol (prepared from reacting 120 mg of sodium with 4 mL of methanol at room temperature) was slowly added. The reaction was stirred over night at room temperature and checked by LCMS. The white precipitate was filtered and the solid washed with cold methanol. After drying, 0.98 g of pure 2,5-dichloro-4-methoxypyrimidine was obtained and this material was used without further purification. 1H-NMR (DMSO): delta 8.61 (s, 1H), 4.05 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5750-76-5, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BAKER-GLENN, Charles; BURDICK, Daniel Jon; CHAMBERS, Mark; CHEN, Huifen; ESTRADA, Anthony; SWEENEY, Zachary Kevin; CHAN, Bryan K.; WO2012/62783; (2012); A1;,
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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 874-14-6, name is 1,3-Dimethyluracil. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 1,3-Dimethyluracil

General procedure: A 0.3M solution of Bu4NClO4 in THF (15 mL) was placed in thecathodic chamber of a divided cell (40 mL beaker, 3 cm diameter, 6 cm height)equipped with a lead cathode (5 X 5 cm2), a platinum anode (2 X 1 cm2),and a ceramic cylindrical diaphragm (1.5 cm diameter). A 0.3 M solution of Et4NOTsin DMF (4 mL) was placed in the anodic chamber (inside the diaphragm). 1,3-Dimethylpyrimidine-2,4(1H,3H)-dione(1a) (140 mg, 1.0 mmol), benzophenone (2a) (368mg, 2.0 mmol), TMSCl (0.64 mL, 5 mmol), and TEA (0.70 mL, 5 mmol) were added tothe cathodic chamber. After 400 C of electricity was passed at a constantcurrent of 200 mA at room temperature under nitrogen atmosphere, the catholytewas evaporated in vacuo. The residue was dissolved in diethyl ether (20 mL)and insoluble solid was filtered off. After removal of the solvent in vacuo, the residue was purified by column chromatography on silica gel(hexanes-EtOAc) to give 3a (305 mg) in 77percent yield.

With the rapid development of chemical substances, we look forward to future research findings about 874-14-6.

Reference:
Article; Kise, Naoki; Miyamoto, Hiroyuki; Hamada, Yusuke; Sakurai, Toshihiko; Tetrahedron Letters; vol. 56; 31; (2015); p. 4599 – 4602;,
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