Pyrimidines

Application of 6623-81-0 , The common heterocyclic compound, 6623-81-0, name is 2,4-Dihydroxy-5-methoxypyrimidine, molecular formula is C5H6N2O3, 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.

Compound 110: To a solution of compound 109 (1.42 g, 10 mmol) in dry acetonitrile (30 mL) was added BSA (10.5 g, 50 mmol). The reaction mixture was stirred at 60 C for 4 h and cooled to room temperature. To the reaction mixture were added compound 103 (5.04 g, 10 mmol) and TMSOTf (2.7 mL, 15 mmol). The resulted reaction mixture was stirred at 60 C for 4 h. Upon completion of the reaction as monitored by TLC, the reaction mixture was treated with methylene chloride and saturated sodium bicarbonate. The organic phase was separated, and the aqueous phase was extracted with methylene chloride. The combined organic phase was dried over anhydrous Na2SO4. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The crude product was purified by flash chromatography on a silica gel column giving 3.8 g desired compound 110 in 65% yield.

The synthetic route of 6623-81-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Roy, Atanu; Conlee, Christopher R.; De Fougerolles, Antonin; Fraley, Andrew W.; EP2918275; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 444731-75-3, N-(2-Chloropyrimidin-4-yl)-N,2,3-trimethyl-2H-indazol-6-amine, 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, 444731-75-3, blongs to pyrimidines compound. Recommanded Product: 444731-75-3

To a solution of Intermediate Example 4 (200 mg, 0.695 mmol) and 5-amino-2- methylbenzenesulfonamide (129.4 mg, 0.695 mmol) in isopropanol (6 ml) was added 4 drops of cone. HCI. The mixture was heated to reflux overnight. The mixture was cooled to rt and diluted with ether (6 ml). Precipitate was collected via filtration and washed with ether. The hydrochloride salt of 5-({4-[(2,3-dimethyl-2H-indazol~6- yl)(methyl)amino]-pyrimidin-2-yl}amino)-2-methylbenzenesulfonamide was isolated as an off-white solid. 1H NMR (400 MHz, d6DMSO+NaHCO3) delta 9.50 (br s, 1 H), 8.55 (br s, 1 H), 7.81 (d, J= 6.2 Hz, 1 H), 7.75 (d, J = 8.7 Hz1 1 H), 7.69 (m, 1 H), 7.43 (s, 1 H), 7.23 (S1 2H), 7.15 (d, J= 8.4 Hz1 1H), 6.86 (m, 1 H), 5.74 (d, J= 6.1 Hz, 1 H), 4.04 (s, 3H), 3.48 (S1 3H)1 2.61 (s, 3H)1 2.48 (s, 3H). MS (ES+, m/z) 438 (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,444731-75-3, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/64753; (2007); A2;,
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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. 22536-63-6, name is 2-Chloro-4-methoxypyrimidine, the common compound, a new synthetic route is introduced below. COA of Formula: C5H5ClN2O

Typical syntheses of these derivatives was performed by reaction of 2-broniopyridine, 2-chloiOpyrimidine, 4-amino-2-chloropyrimidine15, 2-chloro-4-methylpyrimidine165 2-chloro- 4-metlioxypyrimidine17 and 2-amino-4-chloropyrimidine1 with the corresponding 5-arnino-2- substitutedphenols in the presence of HCl, followed by reaction with 4-bromo-2~methyl-2- butene in presence of Cs2CO3 as a base. Compounds 46 and 47 were synthesized by reaction of 2-chloro-5-(pyrimidin-2-ylamino)phenol 35d with 4-methylpent-3-en-2-ol18 and (2- methylcyclopent-l-yl)methanol19, respectively, using Mitsunobu conditions20.

The synthetic route of 22536-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YALE UNIVERSITY; WO2007/38387; (2007); A2;,
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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. 2022-78-8, name is 5-Fluoropyrimidin-2(1H)-one, the common compound, a new synthetic route is introduced below. COA of Formula: C4H3FN2O

EXAMPLE 24 1-(3-Methylphenylthio)methyl-5-fluoropyrimidin-2-one 3-(Chloromethylthio)toluene (6.5 mmol) was added to a solution of 5-fluoropyrimidin-2-one (6.5 mmol) and triethylamine (6.5 mmol) in dichloromethane (75 ml) and the resultant mixture heated under reflux for 2 days. The solvent was then distilled off, the residue triturated with water and the residual material extracted with CCl4. Evaporation of the extracts and crystallisation of the residue from ethyl acetate gave the pure product; 0.40 g (25%), m.p. 124 C. (Found: C57.42; H4.63. Calc. for C12 H11 FN2 OS: C57.59; H4.43) 1 H NMR (DMSO d6); delta 2.28 (Me), 5.17(CH2), 7.2 (Ph), 8.05 (H-4), 8.70 (H-6). IR (KBr): 1670 cm-1 (CO), MS [70 eV, m/z (% rel. int.)]: 250 (8,M), 137(11), 136)36), 135(10), 128(7), 127(100), 100(34), 91(9).

The synthetic route of 2022-78-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nyegaard & Co. A.S.; US4596870; (1986); A;,
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Reference of 933702-55-7, 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 933702-55-7, name is 2-Chloropyrimidine-5-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

2401-2403, in 16 ml of tetrahydrofuran was cooled to 0 C. and 1.6 ml (2.6 mmol) of 1.7 N n-butyl lithium/n-hexane solution was added thereto, and the reaction solution was stirred at room temperature for 30 minutes. The reaction solution was cooled to 0 C. again and then a solution of 0.31 g (2.2 mmol) of 2-chloropyrimidin-5-carbaldehyde in 4 ml of tetrahydrofuran was added to the reaction solution, and the reaction solution was stirred at room temperature for 30 minutes. After completion of the reaction, saturated ammonium chloride aqueous solution was added to the reaction solution and the reaction solution was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride aqueous solution and dried with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was subjected to silica gel column chromatography [n-hexane/ethyl acetate=100/0-80/20 (V/V)] and the fraction including the desired compound was concentrated under reduced pressure to provide 0.17 g of 2-chloro-5-(4,4,4-trifluoro-1-buten-1-yl)pyrimidine.

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 933702-55-7, 2-Chloropyrimidine-5-carbaldehyde.

Reference:
Patent; UBE INDUSTRIES, LTD.; DAIICHI SANKYO COMPANY, LIMITED; Nakamura, Tsuyoshi; Namiki, Hidenori; Terasaka, Naoki; Shima, Akiko; Hagihara, Masahiko; Iwase, Noriaki; Takata, Katsunori; Kikuchi, Osamu; Tsuboike, Kazunari; Setoguchi, Hiroyuki; Yoneda, Kenji; Sunamoto, Hidetoshi; Ito, Koji; US2013/109653; (2013); A1;,
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Related Products of 25193-95-7, 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 25193-95-7, name is 5-(Hydroxymethyl)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To the mixture of Compound 5 (150 mg, 0.51 mmol), DIAD (184.94 mg, 0.91 mmol) and pyrimidin-5-ylmethanol (100.71 mg, 0.91 mmol) in THF (5 mL) was added PPh3 (239.89 mg, 0.91 mmol) and the mixture was stirred at 20 C for 16 hours under N2. The mixture was concentrated, the residue was diluted with NH4C1 (20 mL) extracted with EtOAc (20 mL x 2). The combined organic phase was washed with brine (10 mL), dried over Na2SC>4, filtered, and concentrated to give a residue that was purified by Prep-HPLC (Waters Xbridge (150 mm x 25mm, 5 muiotaeta) A = H20 (10 mM NH4HCO3) and B = CH3CN); 40-70 %B over 10 minutes) to afford Compound 84 as a solid. 1H NMR (OMSO-d6 400MHz) deltaH = 9.14 (s, 1H), 8.92 (s, 2H), 7.81 – 7.74 (m, 3H), 7.51 – 7.44 (m, 4H), 5.19 (s, 2H). LCMS Rt = 1.19 min using Method A, MS ESI calcd. for C19H13F3N3O3 [M+H]+ 388.1, found 388.0.

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 25193-95-7, 5-(Hydroxymethyl)pyrimidine.

Reference:
Patent; PRAXIS PRECISION MEDICINES , INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (244 pag.)WO2018/148745; (2018); A1;,
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Reference of 591-55-9, 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 591-55-9 as follows.

Example 203: Preparation of N4-cyclopropyI-N2-(pyrimidin-5-yl)-5-(trifluoromethyl) pyrimidine-2,4-diamin2-Chloro-N-cyclopropyl-5-(trifluoromethyl)pyrimidin-4-amine (0.070 g, 0.295 mmol) and pyrimidin-5-amine (0.028 g, 0.295 mmol) were mixed in Acetic Acid (1 ml). The mixture was microwaved at 120 C for 10 minutes and then concentrated. 3 mg of product was recovered after automated reverse phase chromatography (water-MeCN eluent). MS calcd for297.1 1 , found 296.90.

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; SALK INSTITUTE FOR BIOLOGICAL STUDIES; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; YALE UNIVERSITY; SHAW, Reuben J.; EGAN, Daniel F.; COSFORD, Nicholas; TURK, Benjamin; VAMOS, Mitchell; PANICKAR, Dhanya Raveendra; CHUN, Matthew; SHEFFLER, Doug; (315 pag.)WO2016/33100; (2016); A1;,
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Related Products of 4983-28-2, 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. 4983-28-2, name is 2-Chloro-5-hydroxypyrimidine, molecular formula is C4H3ClN2O, 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.

2-Chloropyrimidin-5-ol (Intermediate No.86 Step 2, 200 mg,. 1.5 mmol) was dissolved in THF (5 mL) and triphenylphosphine (600 mg, 23 mmol) and 1,4-dioxa- spiro[4.5]decan-8-ol (365 mg, 2.30 mmol) was added, followed by DIAD (0.45 mL, 2.3 mmol). The reaction mixture was stirred at ambient temperature overnight. The reaction mixture was diluted with EtOAc, washed with saturated NaHC03> and the aqueous phase was extracted with. EtOAc. The combined organic extracts were dried over Na2S04, filtered, dry loaded onto silica gel and the cpade residue was purified by flash chromatography (MPLC, 2-20percentDCM-hexane followed-by 5-60percent EtOAc-hexane) to give a crude residue which was further purified by reverse phase preparative HPLC (0-80percent MeCN-H20, 0.05percent TFA). Fractions containing the pure compound were collected and the free base was liberated by an EtOAc extraction and sat.NaHC03 wash to give 2-c oro-5-(l ,4-dioxaspiro[4.5]dec-8-yloxy)pyrimidine as a solid.LRMS (ESI) calc’d for C12H16C1N203 [M+H] +: 271 , Found: 271

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 4983-28-2, 2-Chloro-5-hydroxypyrimidine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; YOUNG, Jonathan; CZAKO, Barbara; ALTMAN, Michael; GUERIN, David; MARTINEZ, Michelle; RIVKIN, Alexey; WILSON, Kevin; LIPFORD, Kathryn; WHITE, Catherine; SURDI, Laura; CHICHETTI, Stephanie; DANIELS, Matthew, H.; AHEARN, Sean, P.; FALCONE, Danielle; OSIMBONI, Ekundayo; WO2011/84402; (2011); A1;,
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Electric Literature of 14001-67-3, 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 14001-67-3 as follows.

To a 100 mL one neck round bottom flask was charged with 2-methylthio-5- bromopyrimidine (1 g, 4.88 mmol) along with pinacoldiborane (1.362 g, 5.36 mmol), potassium acetate (0.957 g, 9.75 mmol), Pd(dppf)CH2C12 (0.178 g, 0.244 mmol) and DMSO (10 ml). The flask was sealed with septum and connected to manifold through a syringe needle. The system was vacuumed and refilled with nitrogen three times and the mixture wasthen stirred and heated in an oil bath of 100 OC for 6 hr. The reaction mixture was black. LCMS showed complete consumption of starting material. After cooled to room temperature, the residue was diluted with ethyl acetate (100 mL) and water (50 ml). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3x). The combined organic phases were washed with water, dried over Mg504, filtered and concentrated. The residue waspurified by MPLC (24 g silica gel, 10 to 60% ethyl acetate in hexanes) to afford ligh yellow solid product 2-(methylsulfanyl)-5 -(4,4,5,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)pyrimidine. LC-MS (ES, m/z): C11H17BN2025: 252; Found: 253 [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,14001-67-3, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DEVITA, Robert, J.; YU, Yang; LIU, Jian; HE, Shuwen; KRIKORIAN, Arto, D.; MILLER, Daniel, J.; WU, Zhicai; YANG, Ginger Xu-Qiang; HONG, Quingmei; LAI, Zhong; ZORN, Nicolas; TING, Pauline, C.; WO2013/130370; (2013); A2;,
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Application of 148550-51-0, 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 148550-51-0, name is Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Using Procedure Y-3 (Table 5) with compound 473 the title compound 474 was obtained (85 mg, 18percent) as a clear oil. MS (m/z): 353.5 (M+3)

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 148550-51-0, Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate.

Reference:
Patent; Forum Pharmaceuticals, Inc.; Rogers, Kathryn; Patzke, Holger; (315 pag.)US2017/749; (2017); A1;,
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