Category: pyrimidines

Reference of 90905-33-2 ,Some common heterocyclic compound, 90905-33-2, molecular formula is C6H6N2O, 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.

4-chloro-N2-methylpyridine-2, 3-diamine (840 mg, 5.33 mmol) and iron (III) chloride hexahydrate (360 mg, 1.33 mmol) were dissolved in DMF (26 ml). 2-Methylpyrimidine-5-carbaldehyde (716 mg, 5.86 mmol) was then added and the reaction was allowed to stir vigorously at 80 open to air for 18 h The reaction mixture was then diluted with 3:. 1 chloroform: IPA and washed with water The combined organic layers. were washed with brine, dried over MgSO 4, and concentrated in vacuo while loading onto silica gel Purification by column chromatography. (silica gel, eluting with a gradient of 0 -60percent 3: 1 EtOAc: EtOH in hexanes) gave 7-chloro -3-ethyl-2- (2- methylpyrimidin-5-yl) -3H-imidazo [4, 5-b] pyridine (Intermediate IV). MS ESI calc’d. for C 13 H 13 ClN 5 [M + 1]+ 274; found 274.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,90905-33-2, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MCGOWAN, Meredeth Ann; ZHOU, Hua; KATZ, Jason D.; YANG, Lihu; METHOT, Joey; LIPFORD, Kathryn Ann; XU, Shimin; FU, Ning; XU, Guoquan; BIAN, Deqian; FU, Jianmin; LI, Yabin; FONG, Kin Chiu; (124 pag.)WO2017/125; (2017); A1;,
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Related Products of 22536-61-4, 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.22536-61-4, name is 2-Chloro-5-methylpyrimidine, molecular formula is C5H5ClN2, molecular weight is 128.56, as common compound, the synthetic route is as follows.

In a sealed glass tube a suspension of l-cyclopropyl-6-(lH-imidazol-5-yl)-3,3-dimethylindolin- 2-one (example 71a, 70 mg), 2-chloro-5-methylpyrimidine (37.0 mg) and cesium carbonate (158 mg) in acetonitrile (1.05 ml) was heated to 120 °C for 30 minutes under microwave irradiation. Then again 18 mg 2-chloro-5-methylpyrimidine and 89 mg cesium carbonate were added and the reaction mixture heated to 120°C under conventional heating for 2 hours. The reaction mixture was concentrated in vacuo and purified by flash chromatography (silica gel, gradient, 0percent to 100percent EtOAc in n-heptane). The title compound was obtained as off white solid (75 mg, 80percent). MS (ESI, m/z): 360.2 [(M+H)+].

Statistics shows that 22536-61-4 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-methylpyrimidine.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HILPERT, Hans; KOLCZEWSKI, Sabine; LIMBERG, Anja; STOLL, Theodor; WO2015/177110; (2015); A1;,
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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. 1920-66-7, name is 4-Amino-2-chloro-5-nitropyrimidine, molecular formula is C4H3ClN4O2, 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. Recommanded Product: 1920-66-7

General procedure: The relevant halogenated heterocycle (1.0equiv.), substituted aniline (2.0 equiv.) and TFA (5.0 equiv.) were takenup in TFE (0.1 M) and heated under microwave irradiation conditionsat 140 C for 30 min before being concentrated in vacuo. The residuewas resuspended in EtOAc:THF (1:1, 20 mL/mmol), washed with saturatedNaHCO3 solution (20 mL/mmol), and the aqueous phase wasfurther extracted with EtOAc:THF (1:1, 3 × 15 mL/mmol). The combinedorganic extracts were washed with brine, dried (MgSO4) andconcentrated in vacuo. The resultant residue was purified via columnchromatography and/or triturated as specified to afford the desired compound.

With the rapid development of chemical substances, we look forward to future research findings about 1920-66-7.

Reference:
Article; Casalvieri, Kimberly A.; Matheson, Christopher J.; Backos, Donald S.; Reigan, Philip; Bioorganic and Medicinal Chemistry; vol. 28; 5; (2020);,
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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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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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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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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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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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Electric Literature of 55583-59-0, 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. 55583-59-0, name is 2,5-Diamino-4,6-dichloropyrimidine, molecular formula is C4H4Cl2N4, 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.

To a solution of a 4,6-dichloropyrimidine analogue (11.2 mmol) and DIPEA (2.9 ml, 16.8 mmol) in dioxane (40 ml) was added tert-butyl piperazine-1-carboxylate (3.12 g, 16.8 mmol). The reaction mixture was heated at 100 C. for overnight. After cooling, the volatile was removed under reduced pressure. The crude residue was diluted with CHCl3 and was washed with a saturated NaHCO3 solution, brine and dried over Na2SO4. After removing the solvents under reduced pressure, the residue was purified by flash chromatography on silica (CH2Cl2/MeOH 50:1), affording the title compound.The following compounds were synthesized according to this procedure:Example 262Synthesis of tert-butyl 4-(2,5-diamino-6-chloropyrimidin-4-yl)piperazine-1-carboxylateThis compound was synthesized from 2,5-diamino-4,6-dichloropyrimidine, yielding the title compound in 94% yield.

According to the analysis of related databases, 55583-59-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN, K.U.LEUVEN R&D; US2012/46278; (2012); A1;,
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Reference of 1448307-66-1, 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. 1448307-66-1, name is 1-(2-Chloropyrimidin-4-yl)-3-methyl-1H-pyrazole-4-carbaldehyde, molecular formula is C9H7ClN4O, 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.

Preparation of (3-methyl-1-(2-(1-methyl-1H-indol-5-ylamino)pyrimidin-4-yl)-1H-pyrazol-4-yl)methanol; Intermediate 2 A round bottomed flask was charged with 1-(2-chloropyrimidin-4-yl)-3-methyl-1H-pyrazole-4-carbaldehyde (400 mg, 1.78 mmol), (5-amino-1-methyl-1H-indol-3-yl)(cyclopropyl)methanone (385 mg, 1.0 equiv.), potassium carbonate (0.74 g, 3.0 equiv), palladium acetate (20 mg, 0.05 equiv), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (Xantphos, 100 mg, 0.1 equiv.) and 40 mL of anhydrous dioxane. After being degassed by nitrogen bubbling, the reaction mixture was heated at 100 C. for 12 hours. To the reaction mixture, water was added to form solids. The resulting solids were collected by filtration, washed with water followed by ethyl acetate to give brown powder (430 mg, 60%). The collected solids were dried in vacuo and then used to next step without further purification; MS (ESI) m/z 401 [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 1448307-66-1, 1-(2-Chloropyrimidin-4-yl)-3-methyl-1H-pyrazole-4-carbaldehyde.

Reference:
Patent; Lee, Jaekyoo; Choi, Jang-Sik; Hwang, Hae-Jun; Song, Ho-Juhn; Kim, Jung-Ho; Kim, Se-Won; Koh, Jong Sung; Lee, Jaesang; Lee, Tae-Im; Choi, Yung-Geun; Park, Sung-Ho; Lee, In Yong; Suh, Byung-Chul; Salgaonkar, Paresh Devidas; Jung, Dong-Sik; US2015/111883; (2015); A1;,
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