Pyrimidines

Reference of 14080-59-2, 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 14080-59-2, name is 4-Chlorothieno[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Compound 208d: 3-[2-(Thieno[2,3-d]pyrimidin-4-ylamino)-phenoxy]- pyrrolidine-1-carboxylic acid tert-butyl ester: A suspension of 3-(2-nitro-phenoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (1.0g, 3.6 mmol, 1.0 eq), 4-chloro-thieno[2,3d]pyrimidine (0.61 g, 3.6 mmol, 1.0 eq) and DIPEA (0.74 g, 5.76 mmol, 1 ,6 eq) in IPA (8 ml) was heated at 1200C for 5 days. The reaction was allowed to cool to room temperature and the solvent removed in vacuo. The resultant residue was purified by column chromatography using ethyl acetate/ cyclohexane [1 :1] as eluent to give the title compound (0.64 g, 1.56 mmol, 43%). 1H NMR indicates desired compound in ca. 95% purity.

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 14080-59-2, 4-Chlorothieno[2,3-d]pyrimidine.

Reference:
Patent; DEVELOGEN AKTIENGESELLSCHAFT; WO2006/136402; (2006); A1;,
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Pyrimidine – Wikipedia

Reference of 5305-40-8 ,Some common heterocyclic compound, 5305-40-8, molecular formula is C5H2Cl2N2O, 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.

Hydrazine hydrate (2.0 ml, 41 mmol) was slowly added to a solution of 4,6- dichloropyrimidine-5-carbaldehyde (7.2 g, 41 mmol) in MeOH (150 ml) -60 0C (nitromethane-dry ice bath) followed by triethylamine (6.8 mL, 49 mmol). The mixture was allowed to warm to rt and stirred for 2 h. MeOH was removed in vacuo and water (150 mL) was added. The mixture was extracted with EtOAc (3 x 80 mL). The combined organic layers were washed with brine (100 mL), dried over Na2SO4, and filtered through a glass funnel. Removal of solvent gave 4-chloro-lH-pyrazolo[3,4-d]pyrimidine (4.45 g, 71%). MS (ESI, pos. ion) m/z: 155 [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,5305-40-8, its application will become more common.

Reference:
Patent; AMGEN INC.; WO2008/153947; (2008); A2;,
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Pyrimidine – Wikipedia

Electric Literature of 5018-38-2, 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. 5018-38-2, name is 4,6-Dichloro-5-methoxypyrimidine. A new synthetic method of this compound is introduced below.

HPLC/MS: rt=1.3 min Synthesis of 6-[4-(1,2,3,4-tetrahydro-1,8-naphthyridin-7-yl)-1-piperidinyl]-5-methoxy-4-chloro-pyrimidine: 2.2 g (12.3 mmoles) of 4,6-dichloro-5-methoxy-pyrimidine solubilized in 25 ml of dimethylacetamide and 3640 mul of diisopropylethylamine are added into a single-necked flask containing 800 mg (3.68 mmoles) of 4-(1,2,3,4-tetrahydro-1,8-naphthyridin-7-yl)-1-piperidine released from its salt. This mixture is heated at 130 C. for 2 hours then concentrated to dryness under vacuum. The residue obtained is taken up in a mixture of water, ethyl acetate and a saturated solution of sodium bicarbonate. The organic phase is separated and the aqueous phase reextracted with ethyl acetate. The combined organic phases are dried over magnesium sulphate then the solvent is evaporated off under vacuum. The residue is chromatographed on alumina eluding with a mixture of cyclohexane and acetate (80-20). 900 mg (Yield=68%) of expected product is obtained in the form of a yellow powder. Preparation of the naphthyridine in free amine form: 2.4 g of naphthyridine is displaced from its salt by 6 mass equivalents of basic amberlyst A21 resin (resin of R-NMe2 type) in a CH2Cl2/MeOH/AcOEt mixture 1/1/1 under stirring for 30 minutes. The resin is washed beforehand and left to swell for 20 minutes in this solvent mixture. This operation must be repeated 3 times for the displacement of the salt to be complete. After filtration of the resin and evaporation of the solvents, 800 mg (3.68 mmoles) of free naphthyridine is obtained. (Yield=88%). TLC: Rf0.4 [alumina, eluent: ethyl acetate cyclohexane (30-70)]1H-NMR (MeOD): ? 1.75 to 1.95 (m, 6H, NH-CH2-CH2-CH2, N-CH2-CH2-CH-CH2); 2.70 (t, 1H, CH2-CH-CH2); 2.8 (m, 2H, NH-CH2-CH2-CH2); 3.15 and 3.75 (2m, 4H, CH2-CH2-N-CH2-CH2); 3.75 (s, CH3-O); 6.4 and 7.15 (2d, 2H, CH?CH naphthyridine); 8.1 (s, 1H, N?CH-N).HPLC/MS: (rt=0.53 min and 2.56 min): 359(M); 360(MH+); 361 (M+2H++).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5018-38-2, 4,6-Dichloro-5-methoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Ruxer, Jean-Marie; Lefrancois, Jean Michel; Heckmann, Bertrand; US2006/52398; (2006); A1;,
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Pyrimidine – Wikipedia

Application of 14080-59-2, 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.14080-59-2, name is 4-Chlorothieno[2,3-d]pyrimidine, molecular formula is C6H3ClN2S, molecular weight is 170.62, as common compound, the synthetic route is as follows.

General procedure: alpha,beta-unsaturated tosylhydrazones 1 (0.11 mmol, 1.1 equiv), heteroaryl chlorides 2 (0.1 mmol, 1 equiv), Cs2CO3 (0.25 mmol, 2.5 equiv) and MeCN (1 mL) were added to a tube. The mixture was stirred at 60 C until the heteroaryl chlorides was completely disappeared for 4-8h. After cooling to room temperature, the mixture was quenched with NH4Cl (2 mL, saturated aqueous solution) and extracted with CH2Cl2 (3 × 2 mL). The combined organic phases were dried over Na2SO4 and solvents removed in vacuo. The residue was purified by flash column chromatography on silica gel with ethyl acetate/petroleum ether (1:10-1:4, V/V) as the eluent, affording the desired product 3 and 4.

Statistics shows that 14080-59-2 is playing an increasingly important role. we look forward to future research findings about 4-Chlorothieno[2,3-d]pyrimidine.

Reference:
Article; Zeng, Lin; Guo, Xiao-Qiang; Yang, Zai-Jun; Gan, Ya; Chen, Lian-Mei; Kang, Tai-Ran; Tetrahedron Letters; vol. 60; 33; (2019);,
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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. 1146629-75-5, name is (4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate. This compound has unique chemical properties. The synthetic route is as follows. name: (4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate

6-(2-methyl-5-nitrophenyl)-1H-indole (1 g, 4.2 mmol) was dissolved in 1,4-dioxane solution (28 mL). (4-chloro-7H-pyrrolo[2,3-d]pyrimidine-7-yl)methyl pivalate (1.35 g, 5.04 mmol) and potassium carbonate (1.74 g, 12.6 mmol) were added, and then a nitrogen gas was injected for 5 minutes to remove the gas included in the mixture solution. Then, the reaction vessel was placed in an oil bath heated to 120 C., and Pd(OAc)2 (95 mg, 0.42 mmol) and Xantphos (365 mg, 0.63 mmol) were added and stirred for 2 hours. After the reaction was completed, it was extracted with ethyl acetate and water. The collected organic layers were dried over anhydrous sodium sulfate and concentrated. The residue was purified by MPLC to obtain the target compound (3.53 g, 72%) as a yellow solid. 1H NMR (400 MHz, CDCl3-d6) delta 8.84 (s, 1H), 8.56 (s, 1H), 8.20 (d, J=2.4 Hz, 1H), 8.11 (dd, J=2.4 Hz, 8.4 Hz, 1H), 7.95 (d, J=3.6 Hz, 1H), 7.73 (d, J=8.0 Hz, 1H), 7.51 (d, J=4.0 Hz, 1H), 7.43 (d, J=8.4 Hz, 1H), 7.21 (dd, J=1.6 Hz, 8.0 Hz, 1H), 6.87 (d, J=3.6 Hz, 1H), 6.79 (d, J=4.0 Hz, 1H), 6.28 (s, 2H), 2.42 (s, 3H), 1.17 (s, 9H)

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, 1146629-75-5, (4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate.

Reference:
Patent; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; SIM, Tae Bo; YOON, Ho Jong; HUR, Woo Young; NAM, Yun Ju; CHOI, Hwan Geun; (17 pag.)US2018/50036; (2018); A1;,
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Related Products of 145783-15-9, 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.145783-15-9, name is 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine, molecular formula is C7H9Cl2N3S, molecular weight is 238.14, as common compound, the synthetic route is as follows.

4,6-Dichloro-2-(propylthio)pyrimidin-5-amine (0.5 g, 2.1 mmol) was dissolved in methanol (2 mL) and supplemented with sec-butylamine (460.0 mg, 6.3 mmol). The reaction mixture was introduced in a sealed vessel and heated at 100C for 90 min. After concentration of the reaction mixture to dryness under vacuum, the residue was purified by silica gel column chromatography.Yield: 81%.Melting point: liquid.*H NMR (DMSO -d6) d 0.87 (t, J=7.4 Hz, 3H, NHCH(CH3)CH2C/ ,), 0.95 (t, J=7.3 Hz, 3H, SCH2CH2CH3), 1.15 (d, J=6.6 Hz, 3H, NHCH(C/ ,)CH2CH3), 1.53 (m, 2H, NHCH(CH3)CH2CH3), 1.64 (h, J=7.3 Hz, 2H, SCH2CH2CH3), 2.93 (t, J=7.2 Hz, 2H, SCH2CH2CH3), 4.01 (hept, J=6.6 Hz, 1H,NHCH(CH3)CH2CH3), 4.81 (s, 2H, NH2), 6.64 (d, J=7.5 Hz, 1H, NHCH(CH3)CH2CH3).13C NMR (DMSO -d6) d 10.5 (NHCH(CH3)CH2CH3), 13.3 (SCH2CH2CH3), 19.8 (NHCH(CH3)CH2CH3), 22.8 (SCH2CH2CH3), 28.6 (NHCH(CH3)CH2CH3), 32.1 (SCH2CH2CH3), 47.9 (NHCH(CH3)CH2CH3), 119.7 (C-5), 137.3 (C-6), 152.0 (C-4), 155.0 (C-2)

Statistics shows that 145783-15-9 is playing an increasingly important role. we look forward to future research findings about 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine.

Reference:
Patent; UNIVERSITE DE LIEGE; LANCELLOTTI, Patrizio; OURY, Cecile; PIROTTE, Bernard; (140 pag.)WO2019/158655; (2019); 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. 51-20-7, name is 5-Bromouracil, the common compound, a new synthetic route is introduced below. Application In Synthesis of 5-Bromouracil

Step 1 . Preparation of 5-[benzyl(methyl)amino]-1 /-/-pyrimidine-2,4-dione 5-Bromouracil (0.15 g, 0.78 mmol) was dispersed in /V-benzylmethylamine (2.0 mL, 15.70 mmol) and heated at 120 C for 1 hr under microwave irradiation. The reaction mixture was diluted with water (1 mL) and concentrated. The white solid obtained was washed with water (10 mL), MeOH (5 mL) and then collected by dispersion in EtOAc (10 mL). The solvent was removed by evaporation to afford the title compound (0.22 g, 86%) as white powder. Analytical data were consistent with those reported in the literature {Tetrahedron2005, 67(12), 3107-31 13). 1H NMR (400 MHz, DMSO-d6): delta 2.42 (s, 3H), 4.07 (s, 2H), 6.62 (s, 1 H), 7.15-7.39 (m, 5H), 10.40 (br s, 1 H), 1 1 .07 (s, 1 H).MS (ESI) m/z: 232 [M-H]+.

The synthetic route of 51-20-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FONDAZIONE ISTITUTO ITALIANO DI TECNOLOGIA; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; UNIVERSITA’ DEGLI STUDI DI PARMA; PIOMELLI, Daniele; REALINI, Natalia; MOR, Marco; PAGLIUCA, Chiara; PIZZIRANI, Daniela; SCARPELLI, Rita; BANDIERA, Tiziano; WO2013/178576; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 37972-24-0, 2-Ethynylpyrimidine, 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, Application In Synthesis of 2-Ethynylpyrimidine, blongs to pyrimidines compound. Application In Synthesis of 2-Ethynylpyrimidine

General procedure: To a stirring solution of 3 (1 eq.) in MeOH (5 vol) was added alkyne(1 eq.) followed by 100 mM aq. CuSO4 (5 mol %) and 100 mM aq. sodium ascorbate (10 mol %). The reaction was poured into water (20 mL) and extracted with DCM (4 x 50 mL). The combined organics were washed with brine (50 mL), dried over anh. MgSO4 and filtered. The volatiles were removed in vacuo and the crude was purified by MPLC over C18 silica gel (Grace Reveleris X2, A: H2O+ 0.1% TFA, B: ACN + 0.1% TFA, 5-25%) then repurified (GraceReveleris X2, A: H2O + 0.1% TFA, B: ACN + 0.1% TFA, 5-100% B) togive a cream powder (16 mg, 9%). LCMS: Rt = 2.21 min, 99 A% 254nm, [M + H]+= 300.8. 1HNMR (600 MHz, DMSO-d6) delta 8.88 – 8.84 (m, 2H), 8.69 (s, 1H),8.06 (s, 1H), 7.44 (t, J = 4.9 Hz, 1H), 4.93 (dd, J = 6.5, 4.4Hz, 2H), 4.80 (dd, J = 6.6, 4.4 Hz, 2H), 1.93 (s, 3H). 13CNMR (150 MHz, DMSO-d6) delta 158.3, 157.8, 151.1,146.5, 138.4, 133.2, 127.3, 120.2, 48.9, 46.0, 12.9. HRMS calcd for C12H12N8NaO2 [M + Na]+, 323.0975; found, 323.0976.

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:
Article; Jarrad, Angie M.; Karoli, Tomislav; Debnath, Anjan; Tay, Chin Yen; Huang, Johnny X.; Kaeslin, Geraldine; Elliott, Alysha G.; Miyamoto, Yukiko; Ramu, Soumya; Kavanagh, Angela M.; Zuegg, Johannes; Eckmann, Lars; Blaskovich, Mark A.T.; Cooper, Matthew A.; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 96 – 102;,
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Electric Literature of 1753-50-0, 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 1753-50-0 as follows.

To a stirred solution of compound CS (0.5 g, 2.95 mmol) in ethanol (10 mL), 2-chloropyrimidine-5-carbonitrile (AF, 0.45 g, 3.25 mmol) and DIPEA (2.52 mL, 14.7 mmol) were added and the reaction mixture was heated to 90C for 16 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using 20% EtOAc/hexane to afford compound CT (0.61 g, 76%) as a white solid. LC-MS: m/z 272.05 [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,1753-50-0, its application will become more common.

Reference:
Patent; VPS-3, INC.; YATES, Christopher, M.; (397 pag.)WO2018/165520; (2018); A1;,
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Application of 3934-20-1 , The common heterocyclic compound, 3934-20-1, name is 2,4-Dichloropyrimidine, molecular formula is C4H2Cl2N2, 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 solution of 2, 4-dichloro-pyrimidine (5. 00 g) in THF (50 mL) was added 70% aqueous EtNH2 (5.40 g). The mixture was stirred at ambient temperature for 1 hr and concentrated under reduced pressure. The residue was dissolved in CHCl3 and the solution was poured into saturated aqueous NaHC03. The two layers were separated and the aqueous layer was extracted with CHC13 (twice). The combined organic layer was dried over MgS04, filtered, concentrated under reduced pressure, and purified by flash chromatography (silica gel, 17% to 50% EtOAc in hexane) to give (2-chloro-pyrimidin-4- yl) -ethyl-amine (3.69 g) and (4-chloro-pyrimidin-2-yl)-ethyl-amine (1.28 g). (2-chloro-pyrimidin-4-yl)-ethyl-amine ; ESI MS m/e 157, M ;’H NMR (500 MHz, CD13) 8 1.26 (t, J= 7.3 Hz, 3 H), 3.16-3. 62 (m, 2 H), 4.80-5. 95 (m, 1 H), 6.23 (d, J= 5.8 Hz, 1 H), 8.02-8. 22 (m, 1 H). (4-chloro-pyrimidin-2-yl)-ethyl-amine ; CI MS m/e 158, M + H+ ;’H NMR (500 MHz, CDCIs) 8 1.23 (t, J= 7.5 Hz, 3 H), 3.42- 3.49 (m, 2 H), 5.30-5. 62 (m, 1 H), 6.54 (d, J= 5.2 Hz, 1 H), 8.02-8. 22 (m, 1 H).

The synthetic route of 3934-20-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; Arena Pharmaceuticals, Inc; WO2005/95357; (2005); A2;,
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Pyrimidine – Wikipedia