Pyrimidines

Related Products of 2972-52-3, 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 2972-52-3, name is 2,4-Dichloro-5-pyrimidinecarbonyl chloride. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2,4-dichloropyrimidine-5-carbonyl chloride (500 mg, 2.38 mmol) in dichloromethane (30 mL) was added methanol (87.6 mg, 2.73 mmol) and diisopropyeihylamine (369 mg, 2,86 mmol) at 0 C. The resulting mixture was stirred for 1 h at 0 C. Then the solvent was removed. The residue (461rng, 94%) was dissolved in IPA (20 ml,) and followed by the addition of trans-4-aminocyclohexanol (301.6 mg, 2.62 mmol) then DIEA (461.4 mg, 3.57 mmol) dropwiseiy. The resulting mixture was stirred at 0 C for 90 min. After which buiyiamine (208,8 mg, 2.86 mmol) was added, followed by DIEA (461.4 mg., 3.57 mmol). The resulting mixture was stirred at room temperature for 3 h. Water was then added. The resulting mixture was extracted with EtOAc (3X). The combined organic layers were dried (Na2SO4, filtered and concentrated. The residue was purified on ISCO to give methyl 2-(butylamino)-4-((trans-4-hydroxycyclohexyl)amino)pyrimidine-5-carboxylate (682.6 mg, 89% over 3 steps). 1H NMR (400 MHz, CDCl3) delta 9.21 (s, 1H), S.77 (s, 1H), 6.29 (s, 1H), 4.81 – 4.64 (m, 1H), 4.51 (s, 3H), 4.46-4.38 (m, 1H), 4.13-4.1 (m, 2H), 2.89-2.81 (m, 2H), 2.74 (d, J – 9.7 Hz, 2H), 2.35 – 2.25 (m, 2H), 2.23 – 2.00 (m, 6H), 1 ,67 (t, J- 7.2 Hz, 3H); 13C NMR (101 MHz, CDCl3) delta 167.9, 162,5, 161.3, 160.3, 95.5, 69.7, 51.2, 48.3, 41. L 33.8, 31 ,7, 30.3, 20.1, 13,8; MS m/z 323.20 [M+H]+

According to the analysis of related databases, 2972-52-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; WANG, Xiaodong; ZHANG, Weihe; KIREEV, Dmitri; LIU, Jing; MCIVER, Andrew Louis; WO2014/85225; (2014); A1;,
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Electric Literature of 287714-35-6, Adding some certain compound to certain chemical reactions, such as: 287714-35-6, name is Methyl 2-chloropyrimidine-5-carboxylate,molecular formula is C6H5ClN2O2, 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 287714-35-6.

The compound obtained in Example 72c (90.0 mg)In N, N-dimethylacetamide was added sodium hydride(60% oily, 16.7 mg), and the mixture was stirred under ice cooling. After 30 minutes,The compound obtained in Example 71a (48.0 mg)And the mixture was stirred at 100 C. for 12 hours. After cooling to room temperature,Saturated ammonium chloride aqueous solution was added, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure.The residue was purified by silica gel column chromatography (ethyl acetate / hexane) to give the title compound (18.0 mg) as a white 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. 287714-35-6, Methyl 2-chloropyrimidine-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DAIICHI SANKYO COMPANY LIMITED; NAGAMOCHI, MASATOSHI; KOZAWA, YUJI; INAGAKI, HIROAKI; GOTANDA, KENTOKU; NOGUCHI, TETSUJI; TORIHATA, MUNEFUMI; YOSHINO, TOSHIHARU; ISOBE, TAKASHI; (113 pag.)JP2016/141632; (2016); A;,
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Synthetic Route of 10320-42-0, 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.10320-42-0, name is 2-Chloro-5-nitropyrimidine, molecular formula is C4H2ClN3O2, molecular weight is 159.5306, as common compound, the synthetic route is as follows.

4-(5-Nitro-pyrimidin-2-yl)-1 ,4-diaza-bicvclo[3.2.2]nonane free base (Intermediate compound)A mixture of 1 ,4-diazabicyclo[3.2.2]nonane (0.87 g, 6.90 mmol), 2-chloro-5- nitro-pyrimidine (1.56 g, 6.27 mmol) and dioxane (75 ml) was stirred at room- temperature for 15 h. Aqueous sodium bicarbonate (20 ml, 10percent) was added followed by extraction with ethylacetate (3 x 20 ml). The organic phase was dried and evaporated and a yellow powder was isolated. Yield 0.86 g (55percent). Mp 135-139°C.

Statistics shows that 10320-42-0 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-nitropyrimidine.

Reference:
Patent; NEUROSEARCH A/S; WO2009/62989; (2009); A1;,
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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.3073-77-6, name is 2-Amino-5-nitropyrimidine, molecular formula is C4H4N4O2, molecular weight is 140.1, as common compound, the synthetic route is as follows.Recommanded Product: 3073-77-6

A. Synthesis of N-(2-aminopyrimidin-5-yl)(tert-butoxy)carboxamide To a suspension of 2-amino-5-nitropyrimidine (0.25 g, 1.78 mmol) in methanol (4 mL) was added tert-butyl (tert-butoxycarbonyloxy)formate (0.5 mL, 2.18 mmol) and 10% Pd/C (96 mg, 0.090 mmol) under argon. The reaction mixture was hydrogenated under 1 atm H2 for 5 hr, filtered through Celite and concentrated in vacuo to give crude N-(2-aminopyrimidin-5-yl)(tert-butoxy)carboxamide (0.435 g). ES-MS (M+H)+=211.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3073-77-6, 2-Amino-5-nitropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Scarborough, Robert M.; Jantzen, Hans-Michael; Huang, Wolin; Sedlock, David M.; Marlowe, Charles K.; Kane-MaGuire, Kim A.; US2002/77486; (2002); A1;,
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Reference of 183438-24-6, 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 183438-24-6, name is 5-Bromo-2-iodopyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 39; 5-Bromo-2-(2-fluorophenyl)pyrimidineA mixture of 5-bromo-2-iodopyrimidine (2.58 mmol, 0.500 g), 2-fluorophenylboronic acid (3.87 mmol, 0.542 g), 2M aqueous solution of K2CO3 (7.76 mmol, 3.9 ml), Pd(PPh3J4 in dioxane (12 ml) was heated at 11O0C overnight. The solvent was evaporated and the solid residue was extracted between water and ethyl acetate. The organic phase was evaporated and the crude residue was purified by chromatography over SiO2 eluting with hexane/ethyl acetate mixtures affording 0.466 g (yield 56%) of the expected product. ESI/MS (m/e, %): 253 [(M+1)+, 100], 255 [(M+1)+, 97].

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 183438-24-6, 5-Bromo-2-iodopyrimidine.

Reference:
Patent; LABORATORIOS ALMIRALL, S.A.; WO2009/21696; (2009); A1;,
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Electric Literature of 5334-35-0 ,Some common heterocyclic compound, 5334-35-0, molecular formula is C6H5ClN4O, 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.

Example 109 l-methyl-6-(4-methylsulfonylpiperazin-l-yl)-5H-pyrazolo[3 4-d]pyrimidin-4-one (1-142) CASE 30893 step 2 The title compound was prepared by condensation (DIPEA/EtOH) of l-(methylsulfonyl)- piperazine (CASRN 55776-43-2) and Intermediate A: -NMR (400MHz, DMSO-i ) delta ppm 11.07 (s, 1H), 7.80 (s, 1H), 3.78-3.74 (m, 7H), 3.18 (t, J = 4.4 Hz, 4H), 2.91 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5334-35-0, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FENG, Jianwen; HAYNES, Nancy-Ellen; HERMANN, Johannes Cornelius; KIM, Kyungjin; LIU, Jin-Jun; SCOTT, Nathan Robert; YI, Lin; ZAK, Mark; ZHAO, Guiling; WO2013/182546; (2013); A1;,
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Application of 1193-21-1, Adding some certain compound to certain chemical reactions, such as: 1193-21-1, name is 4,6-Dichloropyrimidine,molecular formula is C4H2Cl2N2, 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 1193-21-1.

Synthesis of 4-Chloro-6-(4-trifluoromethyl-phenyl)-pyrimidine A mixture under N2 of 4,6-dichloropyrimidine (447 mg, 3.00 mmol, 1.00 eq.), 4-(trifluoromethyl)phenylboronic acid (188 mg, 0.99 mmol, 0.33 eq.), Na2CO3 (1.59 g, 15.00mmol, 5.00 eq.) and tetrakis(triphenylphosphine)palladium (0) (173 mg, 0.15 mmol, 0.05eq.) in acetonitrile (5 mL) was stirred at 80 C for 24 hours and further at 100 C for 18hours. The reaction mixture was allowed to cool down to r.t. and concentrated in vacuo.The residue was partitioned between DCM and sat. aq. NaHCO3 soln. The layers were separated. The aq. phase was extracted with DCM. The comb. org. phases were washed with sat. aq. NaCI soln., dried over MgSO4, and concentrated in vacuo. The residue was purified by prep. HPLC (column: Waters X-Bridge, 18×50 mm, 10 tm, UV/MS, basicconditions) and concentrated in vacuo to afford the title compound as a white solid. LC-MS 4: tR = 0.94 mm; [M+H] = 259.3

According to the analysis of related databases, 1193-21-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; AISSAOUI, Hamed; BOSS, Christoph; CIANA, Claire-Lise; KIMMERLIN, Thierry; SIEGRIST, Romain; WO2015/28989; (2015); A1;,
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Reference of 1193-24-4 , The common heterocyclic compound, 1193-24-4, name is 4,6-Dihydroxypyrimidine, molecular formula is C4H4N2O2, 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.

4,6-Dichloropyrimidine-5-carbaldehyde (9).; In a 5 L 4-neck flask equipped with mechanical stirrer, addition funnel, condenser, thermocouple, and a N2 sweep into an aqueous NaOH scrubbing solution, phosphorous oxychloride (1 L, 10.572 mol, 4.82 equiv) was cooled in an ice/salt bath. N,N-Dimethylformamide (DMF, 320 mL, 4.138 mol, 1.85 equiv) was added dropwise at 0+/-2 C. After addition of 100 mL of DMF (0.5 hr) crystallization occurred and the reaction temperature was increased from 0 to 10 C. Addition was stopped and the mixture was allowed to recool to 2 C. The remaining DMF was added over 2.5 hr at <8 C. The suspension became very thick making stirring difficult. When addition of DMF was complete, the mixture was stirred 0.5 hr at 3-5 C. 4,6-dihydroxypyrimidine (8, 250 g, 2.232 mol) was added portion wise as a solid. After about one third of 4,6-dihydroxypyrimidine was added the reaction mixture became more mobile and a slow exothermic phenomena occurred with the reaction temperature increasing to 12 C. over 0.5 hr. The remaining 4,6-dihydroxypyrimidine was added portion wise over 0.25 hr with the reaction temperature increasing from 12 to 27 C. The reaction temperature was maintained at 25-27 C. with intermittent cooling during which time the yellow suspension became thinner, then thicker once again. After the exothermic phenomenon subsided in about 1 hr, the reaction mixture was heated slowly. At about 55 C. the reaction mixture became extremely thick and the second mild exothermic phenomenon was occurred. The heating mantle was removed while the reaction temperature continued to increase to about 63 C. and remained at this temperature for several minutes before dropping. Heating of the mixture was resumed until gentle reflux (about 100 C.) was attained. At about 95 C. a steady, fairly rapid evolution of HCl began and the reaction mixture gradually thinned and darkened. After about 0.5 hr a clear, brown solution developed with the reflux temperature slowly increasing to 115 C. over 1.25 hr. After a total of 2.5 hr at reflux, the reaction mixture was cooled to room temperature and stirred overnight. Excess POCl3 (as much as possible) was removed under reduced pressure (bath temperature 45-50 C.). The thick residual brown oil was poured very slowly into cold H2O (5 L) in a 20 L separation funnel, adding ice as needed to maintain the aqueous mixture near room temperature. The aqueous mixture was extracted with EtOAc (2×3 L, 1×2 L). The combined EtOAc extracts were washed with H2O (2×2.5 L), saturated NaHCO3 aqueous solution (1 L), brine (1 L), dried over Na2SO4, filtered, and concentrated under reduced pressure (bath temperature at 35 C.) to afford the crude 4,6-dichloropyrimidine-5-carbaldehyde (9, 270 g, 395 g theoretical, 68.4%) as yellow-orange solid. A 20 g portion of this crude material was purified by Kugelrohr distillation (oven temperature at 90-100 C., 225 mTorr) to give 15.3 g of pure 4,6-dichloropyrimidine-5-carbaldehyde (9) as a white solid that turned yellow on standing at room temperature. (On standing crude 9 undergoes slow hydrolysis with formation of HCl. Prior to use in the next step crude 9 was dissolved in a mixture of EtOAc and toluene and filtered to remove insoluble material. The filtrate washed with H2O, saturated NaHCO3 solution, brine, dried over Na2SO4, filtered, and concentrated under reduced pressure and the resulting yellow solid used the following day.) For 9: 1H NMR (CDCl3, 300 MHz) delta ppm 10.46 (s, 1H), 8.89 (s,1H). The synthetic route of 1193-24-4 has been constantly updated, and we look forward to future research findings. Reference:
Patent; Zhou, Jiacheng; Liu, Pingli; Lin, Qiyan; Metcalf, Brian W.; Meloni, David; Pan, Yongchun; Xia, Michael; Li, Mei; Yue, Tai-Yuen; Rodgers, James D.; Wang, Haisheng; US2010/190981; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 6328-58-1, 6-Methyl-2-(methylthio)-1H-pyrimidin-4-one, 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, 6328-58-1, blongs to pyrimidines compound. Recommanded Product: 6-Methyl-2-(methylthio)-1H-pyrimidin-4-one

A mixture of 0.01 mol of 6-methyl-2-(methylsulfanyl)-pyrimidin-4(3H)-one and 0.02 mol of pyrrolidine in 20 mL of butan-1-ol was heated for 15 h at 130140C. The solvent was distilled off, the residue was treated with diethyl ether, and the precipitate was ltered off and dried. Yield 72%, mp 240242C. IR spectrum: nu 1646 cm -1 (C=O). 1 H NMR spectrum, delta, ppm: 1.921.99 m (4H, CH 2 CH 2 ), 2.04 s (3H, CH 3 ), 3.433.51 m (4H, CH 2 NCH 2 ), 5.32 s (1H, 5-H), 10.84 br.s (1H, OH). 13 C NMR spectrum, delta C , ppm: 23.7, 24.7, 46.1, 98.8, 152.2, 163.7, 165.1. Found, %: C 60.21; H 7.26; N 23.20. C 9 H 13 N 3 O. Calculated, %: C 60.32; H 7.31; N 23.45.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6328-58-1, its application will become more common.

Reference:
Article; Pivazyan; Ghazaryan; Azaryan, Zh. A.; Yengoyan; Russian Journal of General Chemistry; vol. 89; 10; (2019); p. 2010 – 2017; Zh. Obshch. Khim.; vol. 89; 10; (2019); p. 1511 – 1519,9;,
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Related Products of 1780-26-3, Adding some certain compound to certain chemical reactions, such as: 1780-26-3, name is 2-Methyl-4,6-dichloropyrimidine,molecular formula is C5H4Cl2N2, 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 1780-26-3.

Example 145 Synthesis of 2-(4-{6-[7-(2,6-dichloro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamino]-2-methyl-pyrimidin-4-yl}-piperazin-1-yl)-ethanol To synthesize the title compound (CLXIX), two intermediate compounds 62 (2-[4-(6-chloro-2-methyl-pyrimidin-4-yl)-piperazin-1-yl]-ethanol) and 63 (7-(2,6-dichloro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamine) shown below were used. To synthesize compound 62, to a solution of 4,6-dichloro-2-methyl-pyrimidine (5.0 g, 31 mmol) and 2-piperazin-1-yl-ethanol (2.7 g, 21 mmol) in dioxane (25 mL) was added DIPEA (3.0 mL, 17 mmol). The mixture was heated at reflux for 16 h. The mixture was allowed to cool to room temperature and poured into water. The reaulting aqueous layer was extracted with EtOAc and the combined organic layers washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated and the residue purified by flash chromatography on silica gel (5-10% MeOH/DCM) to afford compound 62 as a brown liquid (2.1 g, 39%). MS (ESI+): m/z 257.

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. 1780-26-3, 2-Methyl-4,6-dichloropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TargeGen, Inc.; US2005/245524; (2005); A1;,
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Pyrimidine – Wikipedia