Pyrimidines

Synthetic Route of 89487-99-0, 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.89487-99-0, name is 4-Hydroxy-2-(methylthio)pyrimidine-5-carbonitrile, molecular formula is C6H5N3OS, molecular weight is 167.19, as common compound, the synthetic route is as follows.

4-Hydroxy-2-(methylthio) pyrimidine-5-carbonitrile (3 mmol) and m-anisidine (3 mmol) in pentan-1-ol was refluxed for 40 h under nitrogen. The reaction mixture was concentrated in vacuo. The residue was washed with water and dried to afford 4-hydroxy-2-(3-methoxyphenylamino)pyrimidine-5-carbonitrile.

Statistics shows that 89487-99-0 is playing an increasingly important role. we look forward to future research findings about 4-Hydroxy-2-(methylthio)pyrimidine-5-carbonitrile.

Reference:
Patent; Hutchison MediPharma Enterprises Limeted; US2008/255172; (2008); A1;,
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Synthetic Route of 5177-27-5, 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 5177-27-5, name is 5-Amino-2,4-dichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Tri(2-furyl)phosphine (36 mg, 0.16 mmol) and Pd2(dba)3 (20 mg, 0.020 mmol) were added to DMF (10 mL) under N2 at ambient temperature and stirred for 10 min. Subsequently, 2,4-dichloropyrimidine-5-amine (8d) (100 mg, 0.600 mmol) and (2-furyl)tributyltin (0.2 mL, 0.6 mmol) were added. The mixture was stirred at 60 C for 16 h, and evaporated in vacuo. The residue was dissolved in satd KF in THF (20 mL), stirred at ambient temperature for 16 h, and evaporated in vacuo. The residue was placed on top of a flash chromatography column and the product was purified by flash chromatography on silica gel eluting with EtOAc/CH2Cl2/hexane (5:8:12); yield 73 mg (61%), mp 169-170 C, yellow solid. 1H NMR (CDCl3, 500 MHz) delta 8.08 (s, 1H, H-4), 7.61 (dd, J=1.8, 0.7 Hz, 1H, H-5 in furyl), 7.31 (dd, J=3.6, 0.7 Hz, 1H, H-3 in furyl), 6.59 (dd, J=3.6, 1.8 Hz, 1H, H-4 in furyl), 4.71 (s, 2H, NH2); 13C NMR (CDCl3, 75 MHz) delta 152.4 (C-2 in furyl), 149.6 (C-2), 148.2 (C-4), 144.6 (C-5 in furyl), 141.3 (C-6), 135.1 (C-1), 113.9 (C-3 in furyl), 112.8 (C-4 in furyl); MS EI m/z (rel %) 197/195 (38/100, M+), 168 (19), 166 (49), 67 (3); HRMS (EI) calcd for C8H6ClN3O: 195.0199. Found 195.0197.

According to the analysis of related databases, 5177-27-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Read, Matthew L.; Krapp, Andreas; Miranda, Pedro O.; Gundersen, Lise-Lotte; Tetrahedron; vol. 68; 7; (2012); p. 1869 – 1885;,
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Application of 149849-92-3 ,Some common heterocyclic compound, 149849-92-3, molecular formula is C5H3ClN2O2, 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.

To a suspension of 2-chloropyrimindine-4-carboxylic acid (500 mg, 3.15 mmol) and DMF(0.024 mL, 0.32 mmol) in DCM (30 mL) stirred under nitrogen at 0 C was added a 2 Msolution of oxalyl chloride (1.74 mL, 3.47 mmol) in DCM dropwise. The reaction minxturewas allowed to warm to rt and stirred for further 3 h at rt. The reaction minxture wasevaporated in vacuo to give a brown oil. This residue was dissolved in THF (20 mL) and MeOH was added (0.14 mL, 3.5 mmol) dropwise. The reaction minxture was stirred at rt under nitrogen for lh. The reaction minxture was evaporated in vacuo to afford methyl 2- chloropyrimindine-4-carboxylate (780 mg, 4.5 mmol, purity: 80 %, recovery: 143 %) as abrown oil. The compound was used in the next step without purification. LCMS (mlz) 173 and 175 (M+H), retention time: 1.86 mm, LC/MS Method 2.

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. 149849-92-3, 2-Chloropyrimidine-4-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DAUGAN, Alain Claude-Marie; DONCHE, Frederic G.; FAUCHER, Nicolas Eric; GEORGE, Nicolas S.; (243 pag.)WO2018/92089; (2018); A1;,
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Application of 633328-95-7 , The common heterocyclic compound, 633328-95-7, name is 5-Bromo-2-chloro-4-methylpyrimidine, molecular formula is C5H4BrClN2, 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 fourth exemplary Intermediate D, Intermediate D-4, may be used to synthesize compounds of formula I, wherein R1 is heteroaryl substituted with two R4 substituents. A mixture of sodium (111 mg, 4.82 mmol, 1.00 equiv) in methanol (772 mg, 24.1 mmol, 975. pL, 5.00 equiv) was stirred at 25 C for 0.5 h. To this solution was added 5-bromo-2-chloro-4- methyl-pyrimidine (1.00 g, 4.82 mmol, 1.00 equiv) and the mixture was stirred at 25 C for 2 h. The reaction was quenched upon the addition of water (5 mL). The aqueous phase was extracted with ethyl acetate (10.0 mL c 3) and the combined organic phase was washed with brine (10.0 mL x 3), dried over anhydrous Na2S04, filtered and concentrated in vacuo to afford 5-bromo-2- methoxy-4-methyl-pyrimidine (500 mg, 2.46 mmol, 51.1% yield) as a red oil. LCMS: [M+l] 203.1.

The synthetic route of 633328-95-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MIRATI THERAPEUTICS, INC; MARX, Matthew, Arnold; LEE, Matthew, Randolph; BOBINSKI, Thomas, P.; BURNS, Aaron, Craig; ARORA, Nidhi; CHRISTENSEN, James, Gail; KETCHAM, John, Nichael; (225 pag.)WO2019/152419; (2019); A1;,
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Application of 4359-87-9 ,Some common heterocyclic compound, 4359-87-9, molecular formula is C4Cl3N3O2, 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.

Dissolve 2,4,6-trichloro-5-nitropyrimidine (454 mg, 2.0 mmol) and diisopropylethylamine (516 mg, 4.0 mmol) in anhydrous tetrahydrofuran (20 mL), and slowly add dropwise at 0 C. 2,4-difluorobenzylamine (300 mg, 2.1 mmol) was stirred at 0 C for 1 hour. Concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 15: 1) to obtain 34-e (547 mg, yield: 82%) as a yellow solid.

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. 4359-87-9, 2,4,6-Trichloro-5-nitropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanghai Zaiji Pharmaceutical Technology Co., Ltd.; Wang Yuguang; Zhang Nong; Wu Tianzhi; Wu Xinliang; (132 pag.)CN110872297; (2020); A;,
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Adding a certain compound to certain chemical reactions, such as: 22536-63-6, 2-Chloro-4-methoxypyrimidine, 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, SDS of cas: 22536-63-6, blongs to pyrimidines compound. SDS of cas: 22536-63-6

To a 2-dram vial were added (6-arnino-hex-3-ynyl)-carbamic acid tert-butyl ester (0.04 g, 0.2 mmol, Compound 4.3), 2-chIoro-4-methoxy-pyrimidine (0.029 g, 0.2 mmol), 2 ml of s-BuOH, and 0.2 ml of di-isopropylethylamine. The vial was capped and shaken at 130 C for 16 hours. The solvent was filtered and removed using the Gene Vac HT- 12 to give Compound 8.4. ES (+) MS m/e = 321 (M+l).

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

Reference:
Patent; SUNESIS PHARMACEUTICALS; BIOGEN IDEC, INC.; WO2008/5457; (2008); A2;,
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Reference of 115617-41-9, 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 115617-41-9, name is 4,5-Dichloro-6-ethylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 1 Preparation of d,l-4-[1′-(beta-naphthyl)-ethylamino]-5-chloro-6-ethylpyrimidine of the formula STR22 11.98 g of 1-(beta-naphthyl)-1-aminoethane and 20 ml of triethylamine are added to a solution of 12.39 g of 4,5-dichloro-6-ethylpyrimidine in 150 ml of n-butanol. The mixture is boiled under reflux for 12 hours. After concentration of the reaction solution by evaporation, the crude product is dissolved in 20 ml of chloroform, 6 ml of concentrated hydrochloric acid are added, and the product is extracted by shaking with water. The organic phase is separated off and dried with sodium sulfate and the solvent is distilled off, yielding a light-brown oil. The oil is triturated with hexane, whereupon the desired end product crystallises out. Filtration yields 11.6 g of substance; m.p.: 80-81 C. The resulting racemate can be separated into a (+)-enantiomer and its biologically more active (-)-enantiomer by fractional crystallisation with, for example, optically active tartaric acid, or can be resolved by separation on a chiral column by means of HPLC.

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 115617-41-9, 4,5-Dichloro-6-ethylpyrimidine.

Reference:
Patent; Ciba-Geigy Corporation; US5468751; (1995); A;,
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Application of 117516-97-9 , The common heterocyclic compound, 117516-97-9, name is 2-Thioxo-2,3-dihydrothieno[2,3-d]pyrimidin-4(1H)-one, molecular formula is C6H4N2OS2, 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: A suspension of 94 (78 mg, 0.399 mmol, 1.0eq) and NEt3 (66 muL, 0.479 mmol, 1.2 eq) in 1.0 mL DMF was stirred for 15 min at room temperature before 954 (150 mg, 0.479 mmol, 1.2 eq) was added and the reaction mixture was stirred for 16 h at room temperature. The solids were filtered, washed with small amounts of water, methanol and diethyl ether,and the product was dried under vacuum to give the corresponding methyl ester (131 mg, 77%) as a whitesolid, which was subsequently hydrolyzed.

The synthetic route of 117516-97-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fuerst, Rita; Yong Choi, Jun; Knapinska, Anna M.; Smith, Lyndsay; Cameron, Michael D.; Ruiz, Claudia; Fields, Gregg B.; Roush, William R.; Bioorganic and Medicinal Chemistry; vol. 26; 18; (2018); p. 4984 – 4995;,
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Related Products of 304693-66-1 ,Some common heterocyclic compound, 304693-66-1, molecular formula is C6H3F3N2O, 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 2-(trifluoromethyl)pyrimidine-5-carbaldehyde (860 mg, 4.88 mmol) and but-3-en-1 -01 (0.420 mL, 4.88 mmol) in DCM (5.2 mL) was cooled to 0C. MsOH (3.17 mL, 48.8 mmol) was added dropwiseand the RM was stirred at RT for 90 mm. DCM (30 mL) was added, followed by the careful addition of sat. aq. NaHCO3 (30 mL). The organic layer was washed with sat. aq. NaHCO3 (2×30 mL), dried (Na2SO4) and evaporated under reduced pressure. The product was purified by flash chromatography (silica, gradient heptane/EtOAc, 1:0 to 1:1), to give 1.24 g (78%) of the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,304693-66-1, its application will become more common.

Reference:
Patent; GRUeNENTHAL GMBH; SCHUNK, Stefan; REICH, Melanie; JAKOB, Florian; DAMANN, Nils; HAURAND, Michael; KLESS, Achim; ROGERS, Marc; SUTTON, Kathy; WO2015/158427; (2015); 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. 14394-56-0, name is 4-Amino-6-chloro-5-methylpyrimidine, the common compound, a new synthetic route is introduced below. Product Details of 14394-56-0

Example 50 5-methyl-4-N-{1-[3-(pyridin-2-yl)indolizin-2-yl]ethyl}pyrimidine-4,6-diamine To a solution of 1-[3-(pyridin-2-yl)indolizin-2-yl]ethan-1-amine Q2 (0.100 g, 0.42 mmol) in t-BuOH (4.5 mL), 6-chloro-5-methylpyrimidin-4-amine (0.060 g, 0.42 mmol) was added followed by DIPEA (0.146 mL, 0.84 mmol) and the resulting mixture was heated to reflux for 24 h. Additional 1-[3-(pyridin-2-yl)indolizin-2-yl]ethan-1-amine Q2 (0.100 g, 0.42 mmol) was added over 48 h heating to reflux. The solvent was removed and the crude was dissolved in n-BuOH (4.5 mL); DIPEA (0.146 mL, 0.84 mmol) was added and the reaction was heated to 130 C. for 10 days. An additional experiment was performed: to a solution of 1-[3-(pyridin-2-yl)indolizin-2-yl]ethan-1-amine Q2 (0.059 g, 0.25 mmol) in n-BuOH (2.7 mL), 6-chloro-5-methylpyrimidin-4-amine (0.036 g, 0.25 mmol) was added followed by DIPEA (0.087 mL, 0.50 mmol) and the resulting mixture was heated under MW irradiation for 2 h at 120 C. and for 2 h at 150 C. Then the mixture was heated under thermal conditions at 130 C. for 24 h. Additional 1-[3-(pyridin-2-yl)indolizin-2-yl]ethan-1-amine Q2 (0.059 g, 0.25 mmol) was added over 10 days continuing the heating at 130 C. The two reaction mixtures were combined, the solvent was removed and the crude was partitioned between DCM/MeOH 4/1 and water. The organic phase was dried over sodium sulfate, the solvent was removed under reduced pressure and the crude was purified by flash chromatography on Biotage silica-NH cartridge (cyclohexane:EtOAc=50:50 to 40:60); two further purifications by flash chromatography on Biotage silica cartridge (DCM to DCM_MeOH=98:2) were required to afford title compound as a dark yellow solid (0.0207 g). MS/ESI+ 345.2 [MH]+, Rt 0.56 min (Method A). 1H NMR (400 MHz, DMSO-d6) delta ppm 8.78 (d, 1H), 8.69-8.74 (m, 1H), 7.80-7.92 (m, 2H), 7.77 (s, 1H), 7.46 (d, 1H), 7.27-7.35 (m, 1H), 6.76-6.83 (m, 1H), 6.67 (s, 1H), 6.54-6.61 (m, 1H), 6.24-6.33 (m, 1H), 5.85 (br. s., 2H), 5.60-5.70 (m, 1H), 1.80 (s, 3H), 1.41 (d, 3H).

The synthetic route of 14394-56-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; BIAGETTI, Matteo; ACCETTA, Alessandro; CAPELLI, Anna Maria; GUALA, Matilde; RETINI, Michele; US2015/361100; (2015); A1;,
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