Category: pyrimidines

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. 19858-50-5, name is (2-(Methylthio)pyrimidin-5-yl)methanol, molecular formula is C6H8N2OS, 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. Quality Control of (2-(Methylthio)pyrimidin-5-yl)methanol

To the solution of (2-(methylthio)pyrimidin-5-yl)methanol (0.88 g, 5.6 mmol) in DCM (20 ml) at 0°C was added triphenylphosphine (2.1 g, 7.9 mmol) and carbon tetrabromide(2.6 g, 7.9 mmol). The resulting solution was stirred at 0°C for 1 hour. The reaction mixture was purified on silica gel column using EtOAc/hexane as eluting solvents to give 5- (bromomethyl)-2-(methylthio)pyrimidine. LC/MS: (M+ 1 ): 218.90; 220.90.

With the rapid development of chemical substances, we look forward to future research findings about 19858-50-5.

Reference:
Patent; MERCK SHARP & DOHME CORP.; TANG, Haifeng; YANG, Shu-Wei; MANDAL, Mihir; SU, Jing; LI, Guoqing; PAN, Weidong; TANG, Haiqun; DEJESUS, Reynalda; PAN, Jianping; HAGMANN, William; DING, Fa-Xiang; XIAO, Li; PASTERNAK, Alexander; HUANG, Yuhua; DONG, Shuzhi; YANG, Dexi; WO2015/171474; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 29458-38-6, 6-Methoxypyrimidine-2,4(1H,3H)-dione, 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, 29458-38-6, blongs to pyrimidines compound. Formula: C5H6N2O3

A mixture of 2,4-dihydroxy-6-methoxypyrimidine (15g, 0.106mol) in phosphorus (III) oxychloride (400ml) was heated under reflux for 4 hours to give solution. Excess phosphorus (IQ) oxychloride was removed by evaporation, the residue treated with ice/water and extracted with EtOAc. The combined extracts were washed with water, dried (Na2SO4) . and the solvent removed by evaporation to give 2,4-dichloro-6-methoxypyrimidine (5.5g, 30%) as an oil; NMR Spectrum 3.96 (s, 3H), 6.63 (s, IH); Mass Spectrum 179 [MH]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,29458-38-6, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/109026; (2006); A1;,
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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. 890094-38-9, name is 2-Chloro-N-isopropyl-5-nitropyrimidin-4-amine. A new synthetic method of this compound is introduced below., Recommanded Product: 890094-38-9

4-(4-methylpiperazinyl)phenylamine(3.8g) was added to a solution of Compound 2-3(4.3g) in n-butanol(150ml). The mixture was reacted at 90C for 3 hours, cooled to room temperature, filtered, washed and dried to obtain a red solid(6.2g) in a yield of 84.1%. 1H NMR(400 MHz, CDCl3): delta 9.02(s, 1H), 8.42(s, 1H), 7.63(s, 1H), 7.51(s, 2H), 6.95(m, 2H), 4.41(m, 1H), 3.22(t, J=4.8Hz, 4H), 2.61(t, J=4.8Hz, 4H), 2.37(s, 3H), 1.33(d, J=6.4Hz, 6H)ppm.

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, 890094-38-9, 2-Chloro-N-isopropyl-5-nitropyrimidin-4-amine.

Reference:
Patent; Si Chuan University; CSPC Zhongqi Pharmaceutical Technology (Shijiazhuang) Co., Ltd.; YANG, Shengyong; WEI, Yuquan; EP2578584; (2013); A1;,
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Related Products of 199678-12-1, Adding some certain compound to certain chemical reactions, such as: 199678-12-1, name is 4-Pyrimidin-2-yl-benzoic acid,molecular formula is C11H8N2O2, 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 199678-12-1.

Under an argon atmosphere, diethyl cyanophosphonate (0.27 mL, 1.80 mmol) and triethylamine (0.52 mL, 3.75 mmol) were added to a solution of compound 12 (303 mg, 1.50 mmol) and 4-pyrimidin-2-ylbenzoic acid (300 mg, 1.50 mmol) in dehydrated N,N-dimethylformamide (10 mL) at 0 C and the mixture was left to stand overnight. The reaction mixture was poured into saturated aqueous sodium hydrocarbonate and the whole was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate 1:1 v/v) to afford 364 mg (70%) of the title compoundas a white solid. 1H NMR (400 MHz, CDCl3) delta 8.83 (d, J = 4.8 Hz, 2H), 8.50 (d, J = 8.4 Hz, 2H), 7.88 (d, J = 8.4 Hz, 2H), 7.36(dd, J = 7.2, 1.6 Hz, 1H), 7.27 (ddd, J = 8.0, 8.0, 1.8 Hz, 1H), 7.23 (t, J = 4.8 Hz, 1H), 6.94 (ddd, J 7.6, 7.6, 0.8 Hz, 1H), 6.90 (d, J = 8.4 Hz,1H), 6.80 (t, J = 5.8 Hz, 1H), 4.69 (d, J = 5.6 Hz, 2H), 4.01 (t, J = 6.6 Hz,2H), 1.91 – 1.82 (m, 2H), 1.07 (t, J = 7.4 Hz, 3H).

According to the analysis of related databases, 199678-12-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ohashi, Masao; Gamo, Kanae; Tanaka, Yuta; Waki, Minoru; Beniyama, Yoko; Matsuno, Kenji; Wada, Jun; Tenta, Masafumi; Eguchi, Jun; Makishima, Makoto; Matsuura, Nobuyasu; Oyama, Takuji; Miyachi, Hiroyuki; European Journal of Medicinal Chemistry; vol. 90; (2015); p. 53 – 67;,
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Electric Literature of 1513-69-5, 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 1513-69-5 as follows.

Example 15: 4-chloro-6-(trifluoromethyl)pyrimidin-2-amine (24)2-Amino-6-(trifluoromethyl)pyrimidin-4-ol (200 mg, 1.1 mmol) is dissolved in POCI3 (3 eq., 0.3 ml_, 3.3 mmol) and dimethylaniline (0.28 ml_, 2 eq.) is added. The reaction mixture is heated at 7O0C for 4 h. The resulting mixture is poured into a mixture of ice-water, and the resulting precipitate is collected to yield the desired compound 24 in 59%. ESI-MS m/z 198 [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,1513-69-5, its application will become more common.

Reference:
Patent; COVALYS BIOSCIENCES AG; WO2006/114409; (2006); A1;,
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Related Products of 99420-75-4 ,Some common heterocyclic compound, 99420-75-4, molecular formula is C6H6N2O2, 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 5-methylpyrimidine-2-carboxylic acid (1 g, 7.24 mmol) in DMF (72.4 ml) was added 5-methylpyrimidine-2-carboxylic acid (1 g, 7.24mmol), and N,0- dimethylhydroxylamine hydrochloride (0.777 g, 7.96 mmol). The mixture was cooled to 0 C and 1-propanephosphonic acid cyclic anhydride, 50 wt. % solution in EtOAc (9.21 ml, 14.48 mmol) was added droppwise. The mixture was allowed to warm to RT overnight. LCMS indicated complete conversion to product. The mixture was diluted with water, extracted with CHC13:IPA (3: 1) and washed with brine and NaHC03. The mixture was dried over Na2S04, concentrated in vacuo and purified by silica gel chromatography (0-100% heptane s:EtO Ac) to yield N-methoxy-N,5-dimethylpyrimidine- 2-carboxamide (0.7 g, 3.86 mmol, 53.4 % yield). NMR (500 MHz, CDC13) delta 8.61 – 8.69 (m, 2 H) 3.61 – 3.79 (m, 3 H) 3.27 – 3.47 (m, 3 H) 2.34 – 2.45 (m, 3 H). LCMS-ESI (pos.) m +.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,99420-75-4, its application will become more common.

Reference:
Patent; AMGEN INC.; CHEN, Yinhong; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; HARVEY, James S.; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; PATTAROPONG, Vatee; SWAMINATH, Gayathri; YEH, Wen-Chen; RAMSDEN, Philip Dean; SHARMA, Ankit; (321 pag.)WO2018/93576; (2018); A1;,
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Related Products of 1196152-00-7 ,Some common heterocyclic compound, 1196152-00-7, molecular formula is C7H7ClN2O2, 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.

3-(2-chloropyrimidin-4-yl)-l-methyl-lH-pyrazol-5-amine (9.C). To a solution of acetonitrile (0.19 ml, 3.60 mmol) in THF 4.0 ml was slowly added butyllithium (1.5 ml, 2.5M solution in hexanes, 3.77 mmol) at -78 0C and the mixture was stirred at -78 0C for 50 min. Ethyl 2-chloropyrimidine-4-carboxylate, 9.B (0.64 g, 3.43 mmol) in THF (3.0 ml) was added dropwise at -78 0C. The reaction mixture was continued to stirre at -78 0C for Ih. The reaction mixture was allowed to warm up to room temperature and stirred for 1 h. The reaction was quenched by addition of water (15.0 ml). The aquouse layer was acidified to pH = 5 with IN HCl, and extracted with ethyl acetate (30 x 3 ml). The combined organic layer was washed with brine (20 ml) and dried over Na2SO4. The solvent was removed to give the intermediate ketonitrile as a dark brown solid. The crude ketonitrile was treated with methyl hydrazine (0.37 ml, 6.86 mmol) in methanol (6.0 ml) and 2N HCl (3.0 ml) at 80 0C for 6 h. LC-MS results indicated the product was formed. The crude mixture was purified by preperative HPLC to give 9.C. 0.23g, yield 32%. MS ESI (pos.) m/e: 209.9 (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,1196152-00-7, its application will become more common.

Reference:
Patent; AMGEN INC.; DU, Xiaohui; FU, Zice; HOUZE, Jonathan, B.; JIAO, Xianyun; KIM, Yong-jae; LI, Leping; LIU, Jinqian; LIZARZABURU, Mike; MEDINA, Julio; SHEN, Wang; TURCOTTE, Simon; YU, Ming; WO2010/93849; (2010); A2;,
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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. 64951-06-0, name is Ethyl imidazo[1,2-a]pyrimidine-2-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 64951-06-0

To a stirred solution of ethyl imidazo[l ,2-alpha]pyrimidine-2-carboxylate or ethyl imidazo[1,2-a]pyrimidine-3-carboxylate (1 g, 5.2 mmol) in ethanol (40 mL) was added hydrazine monohydrate (0.28 mL, 5.7 mmol). The reaction was heated to 75 C for 16 h and was concentrated under reduced pressure. The resulting light yellow solid was suspended in diethyl ether and filtered to collect ethyl 2-amino-1H-imidazole-4- carboxylate (800 mg, 100%) as a white solid. [00243] 1E NMR (400 MHz, CD3OD) 5 7.27 (s, 1H), 4.24 (q, J= 7.0 Hz, 2H), 1.31(t, J= 7.0 Hz, 3H).[00244] 13C NMR (500 MHz, CD3OD) delta 165.5, 156.1, 131.8, 125.7, 63.8, 17.3.[00245] HPLC Phenomenex LUNA C- 18 4.6 x 50 mm, 0 to 100% B over 4 minutes, 1 minutes hold time, A = 90% water, 10% methanol, 0.1% TFA, B = 10% water, 90% methanol, 0.1% TFA, RT = 0.46 min, 100% homogeneity index.[00246] Anal. Calcd for C6H9N3O2: C, 46.44; H, 5.84; N5 27.08. Found: C, 46.17;H, 5.65; N, 27.28.[00247] HRMS: Anal. Calcd. for C6Hi0N3O2 156.0773 found: 156.0779 (M+H)+.

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, 64951-06-0, Ethyl imidazo[1,2-a]pyrimidine-2-carboxylate.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2006/71752; (2006); A1;,
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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. 5193-88-4, name is 4-Chloro-5,6-dimethoxypyrimidine. A new synthetic method of this compound is introduced below., Product Details of 5193-88-4

A solution of 4-chloro-5,6-dimethoxypyrimidine, 1 (5g, 28.64 mmol) in dry methanol (100 mL) was hydrogenated at 1 atm H2 gas pressure using Pd (10%) on carbon (1 g) as catalyst for 3 hours. After completion of the reaction, the reaction mixture was filtered through celite pad and concentrated to dryness to get (4 g, 99 %) of pure 4,5-dimethoxypyrimidine, 2, as a white solid. UPLC = Calculated for C6H8N202 140.14, Observed = 141.1

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, 5193-88-4, 4-Chloro-5,6-dimethoxypyrimidine.

Reference:
Patent; FORGE THERAPEUTICS, INC.; NAMMALWAR, Baskar; TENG, Min; TAGANOV, Konstantin; PUERTA, David T.; (132 pag.)WO2017/83431; (2017); A2;,
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Synthetic Route of 946161-16-6 ,Some common heterocyclic compound, 946161-16-6, molecular formula is C12H17ClN4O4, 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 mixture of 5 (20.0 g, 63.1 mmol) and reduced iron (14.1 g, 253 mmol) in toluene (100 mL) were added AcOH (1.14 g, 18.9 mmol) and H2O (10 mL) in this order, and the mixture was stirred at 70-80 C for 3 h under N2 atmosphere. To the mixture was added 6 M HCl (100 mL) with vigorous stirring, and the mixture was stirred at 70-80 C for 1 h. After cooling to room temperature, the mixture was filtered and insoluble matter was washed with H2O (40 mL) and EtOAc (40 mL). To the combined filtrate were added EtOAc (160 mL) and H2O (60 mL), and the layers were separated. The aqueous layer was extracted with EtOAc (2 * 200 mL), and the combined organic layer was washed with 10% aqueous NaCl (2 * 100 mL) and saturated aqueous NaHCO3 (200 mL). The organic layer was concentrated in vacuo until the weight of the mixture became approximately 60 g. EtOH (100 mL) was added and the mixture was concentrated in vacuo until the weight of the mixture became approximately 60 g. EtOH (100 mL) was added and the mixture was concentrated in vacuo again until the weight of the mixture became approximately 60 g. To the resulting mixture was added EtOH (20 mL), and H2O (90 mL) was added dropwise. The mixture was cooled to 0-10 C and stirred for 1 h, and then filtrated. Wet solids were washed with EtOH/H2O (1:2, 40 mL) and dried in vacuo at 50 C to give 6 (12.7 g, 80%) as a white solid. Mp 200-201 C; 1H NMR (600 MHz, CDCl3) delta 0.94 (t, J = 7.6 Hz, 3H), 1.37 (d, J = 6.8 Hz, 3H), 1.41 (d, J = 6.8 Hz, 3H), 1.81 (dt, J = 14.5, 7.5 Hz, 1H), 1.99 (ddd, J = 14.5, 7.5, 3.0 Hz, 1H), 4.28 (dd, J = 7.4, 3.2 Hz, 1H), 4.59 (spt, J = 6.8 Hz, 1H), 7.71 (s, 1H), 9.80 (br s, 1H); 13C NMR (151 MHz, CDCl3) delta 8.6, 19.8, 20.9, 27.7, 49.2, 58.6, 117.8, 139.1, 151.9, 154.4, 165.8; IR (ATR) 3229, 2964, 1692, 1655, 1604, 1476, 1410, 1365, 1269, 1237, 1194, 1155, 1127, 1088, 1002, 932, 773, 688, 558, 411, 401 cm-1; HRMS (ESI): [M+H]+ calcd for C11H16ClN4O, 255.1007; found, 255.1007. Optical purity: 99.4% ee (chiral HPLC condition B).

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. 946161-16-6, (R)-Methyl 2-((2-chloro-5-nitropyrimidin-4-yl)(isopropyl)amino)butanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ishimoto, Kazuhisa; Nakaoka, Keiichiro; Yabe, Osamu; Nishiguchi, Atsuko; Ikemoto, Tomomi; Tetrahedron; vol. 74; 39; (2018); p. 5779 – 5790;,
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