Day: November 18, 2020

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. 56-09-7, name is 2-Amino-6-hydroxypyrimidin-4(3H)-one. A new synthetic method of this compound is introduced below., 56-09-7

1.1 Preparation of 2-Amino-4,6-dichloro-5-pyrimidine Carbaldehyde Phosphorus oxychloride (21.6 ml; 0.236 mol) was cooled in an ice-bath (~5 C.) before slow addition of dry N,N-dimethylformamide (DMF, 7.0 ml) over 15 mins. No precipitate occurred as previously reported, and the reaction mixture was removed from the ice-bath. Commercially available 2-Amino-4,6-dihydroxypyrimidine (5.6 g; 0.044 mol) was added in small portions over 30 mins. The resulting suspension was heated at 90 C. for 1 h, then at 105 C. for a further 5 h. forming a red-brown solution which was chilled at 4 C. overnight. Distillation of 3-4 ml of excess phosphorus oxychloride at atmospheric pressure produced a viscous suspension which was poured into ice-water (100 ml). A gum formed which dissolved as the temperature of the water increased to 20 C. Ammonium hydroxide was added dropwise until the solution reached pH 7 and a yellow precipitate formed which was collected by filtration. The product was recrystallized from ethyl acetate (5.15 g; 0.027 mol; 61%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,56-09-7, 2-Amino-6-hydroxypyrimidin-4(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Cancer Research Campaign Technology Limited; US6677345; (2004); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

108-79-2, 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. 108-79-2, name is 4,6-Dimethylpyrimidin-2(1H)-one. This compound has unique chemical properties. The synthetic route is as follows.

Example 246 Methyl-phenyl-carbamic Acid 4,6-dimethyl-pyrimidin-2-yl Ester A solution of 4,6-dimethyl-2-hydroxypyrimidine (0.37 g, 3.00 mmol)), 1-methyl-3-(methyl-phenyl-carbamoyl)-3H-imidazol-1-ium iodide (1.03 g, 3.00 mmol) and triethylamine (0.42 ml, 3.00 mmol) in acetonitrile (15 ml) was stirred at room temperature for 18 hours. The solvent was evaporated in vacuo and the residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane (50:50)) yielding the title compound (0.46 g, 60% yield) as a white solid. 1H NMR (300 MHz, CDCl3): delta 2.48 (s, 6H), 3.43 (br.s, 3H), 6.92 (br.s, 1H), 7.22 (m, 1H), 7.37 (m, 4H); HPLC-MS (Method A): m/z=258 (M+H); Rt=2.77 min.

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 108-79-2, 4,6-Dimethylpyrimidin-2(1H)-one.

Reference:
Patent; Ebdrup, Soren; de Jong, Johannes Cornelis; Jacobsen, Poul; Hansen, Holger Claus; Vedso, Per; US2003/166644; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 302964-08-5, 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, 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, 302964-08-5, blongs to pyrimidines compound. 302964-08-5

To the stirred suspension of compound 5 (10.0 g, 0.03 mol), in n-pentanol (120.0 mL) was added N-Boc piperazine(9.5g, 0.05 mol)) and N,N-diisopropylethylamine (DIPEA) (6.6 g, 0.06 mol) and refluxed for 8h, cooled to 25-30C and charged water (80.0 mL). The precipitated solid was collected by vacuum filtration and washed the wet cake with n-pentanol (15.0 mL) followed by water (30.0 mL), yielded the intermediate 3 (11.6 g, 84%) as off white solid.MR: 293-295C; IR (KBr, cm-1): 3397.4 (N-H), 3061.7 (Ar C-H), 1617.0 (amide C=O); 1706.9 ( Boc C=O); 1HNMR spectrum (400 MHz, DMSO-d6), delta, ppm (J, Hz): 11.53 (bs, 1H, thiazole-NH), 9.89 (s, 1H, amide-NH), 8.23(s, 1H, thiazole-H), 7.40 (d, 1H, J =6.9, Ar-H), 7.30-7.23 (m, 2H, Ar-H), 6.06 (s, 1H, pyrimidine-H), 3.53 (bs, 4H,4piperazine-CH2), 3.42 (bs, 4H, piperazine-CH2), 2.42 (s, 3H, Ar-CH3), 2.24 (s, 3H, pyrimidine-CH3), 1.40 (s, 9H,Boc-CH3); 13C NMR spectrum (100 MHz, DMSO-d6), delta, ppm: 165.2 (pyrimidine-C), 162.4 (pyrimidine-C), 161.9(pyrimidine-C), 160.1 (amide-C), 156.9 (thiazole-C), 151.4 (Boc-C), 140.5 (Ar-C), 139.1 (thiazole-C), 133.7(thiazole-C), 132.0 (Ar-C), 129.5 (Ar-C), 128.4 (Ar-C), 127.6 (Ar-C), 125.1 (pyrimidine-C), 81.6 (pyrimidine-C),80.2 (Boc-C), 50.2 (piperazine-2C), 49.9 (piperazine-2C), 29.1 (Boc-CH3), 25.6 (Ar-CH3), 18.2 (pyrimidine-CH3);HPLC Purity 96.7%; MS (ESI) m/z 544.1 [M + H] +; Anal. Calcd % for C25H30ClN7O3S: C 55.19; H 5.56; N 18.02.Found: C 55.07; H 5.41; N 18.17.

With the rapid development of chemical substances, we look forward to future research findings about 302964-08-5.

Reference:
Article; Suresh, Garbapu; Nadh, Ratnakaram Venkata; Srinivasu, Navuluri; Yennity, Durgaprasad; Synthetic Communications; vol. 47; 17; (2017); p. 1610 – 1621;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1004-38-2, 2,4,6-Triaminopyrimidine, 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, 1004-38-2, blongs to pyrimidines compound. 1004-38-2

General procedure: A 10 mL Schlenk tube was charged with III (0.0174 g, 0.01 mmol), N,N’-diisopropylcarbodiimide (0.504 g, 4 mmol), and 1,4-diaminobenzene (0.216 g, 2 mol) under dried argon. The resulting mixture was stirred at 25 C for 2 h. The reaction mixture was extracted with ether and filtered to give a clean solution. After removing the solvent under vacuum, the residue was recrystallized in ether to provide a white solid 25 in 99% yield.

With the rapid development of chemical substances, we look forward to future research findings about 1004-38-2.

Reference:
Article; Zhang, Xingmin; Wang, Chuanyong; Qian, Cunwei; Han, Fubin; Xu, Fan; Shen, Qi; Tetrahedron; vol. 67; 45; (2011); p. 8790 – 8799;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 7226-23-5, name is 1,3-Dimethyltetrahydropyrimidin-2(1H)-one. This compound has unique chemical properties. The synthetic route is as follows. 7226-23-5

EXAMPLE 7 3-Cyclopentyl-N-thiazol-2-yl-2-(4-thiophen-2-yl-phenyl)-propionamide A solution of diisopropylamine (7.7 mL, 54.88 mmol) in dry tetrahydrofuran (23 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrirnidinone (10 mL) was cooled to -78 C. under nitrogen and then treated with a 2.5M solution of n-butyllithium in hexanes (22.0 mL, 54.88 mmol). The reaction mixture was stirred at -78 C. for 30 min and then treated dropwise with a solution of 4-bromophenylacetic acid (5.62 g, 26.13 mmol) in dry tetrahydrofuran (23 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (10 mL). The reaction mixture turned dark in color and was allowed to stir at -78 C. for 1 h, at which time, a solution of iodomethylcyclopentane (5.76 g, 27.44 mmol) in a small amount of dry tetrahydrofuran was added dropwise. The reaction mixture was allowed to warm to 25 C. where it was stirred for 24 h. The reaction mixture was quenched with water and then concentrated in vacuo to remove tetrahydrofuran. The aqueous residue was acidified using a 10% aqueous hydrochloric acid solution. The resulting aqueous layer was extracted with ethyl acetate (2*100 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 3/1 hexanes/ethyl acetate) afforded 2-(4-bromo-phenyl)-3-cyclopentyl-propionic acid (3.88 g, 50%) as a light yellow solid: mp 91-93 C.; EI-HRMS m/e calcd for C14H17BrO2 (M+) 296.0412, found 296.0417.

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, 7226-23-5, 1,3-Dimethyltetrahydropyrimidin-2(1H)-one.

Reference:
Patent; Corbett, Wendy L.; Haynes, Nancy-Ellen; Sarabu, Ramakanth; US2002/2190; (2002); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

672-41-3, 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. 672-41-3, name is 6-(Trifluoromethyl)pyrimidin-4-amine, molecular formula is C5H4F3N3, 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.

Under Ar(g), to a mixture of 2-chloropyrazine (1) (252mg, 2.2mmol), 4- amino-6-(trifluoromethyl)pyrimidine (2) (326mg, 2.0mmol), Cs2C03 (1.3g, 4.0mmol) was added degassed dry 1 ,4-dioxane (13mL). The reaction mixture was then flushed with Ar(g) for 1 min before Pd2(dba)3 (92mg, 0.1 mmol) and Xantphos (127mg, 0.22mmol) were added. The reaction mixture was heated up to 90C for 40h. It was then cooled down to rt. EtOAc (15ml_), H20 (10mL) and brine (5ml_) were added to the reaction mixture. The organic phase was separated and the aqueous phase was extracted with EtOAc (15ml_). The organic layers were combined and Pd-scavenger (MP-TMT, ~400mg, 1.3mmol/g) was added. This was shaken for several hours followed by filtration. The filtrate was concentrated in vacuo, dissolved in DMSO (4ml_) and purified by basic prep LCMS to yield (3) as a solid (314mg, 65%). (0650) LCMS (ES): Found 242.2 [M+Hf.

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. 672-41-3, 6-(Trifluoromethyl)pyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KARUS THERAPEUTICS LIMITED; SHUTTLEWORTH, Stephen Joseph; GATLAND, Alice Elizabeth; FINNEMORE, Daniel John; ALEXANDER, Rikki Peter; SILVA, Franck; CECIL, Alexander; (233 pag.)WO2019/166824; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

5750-76-5, 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. 5750-76-5, name is 2,4,5-Trichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

(E)-4-(2-butoxyvinyl)-2,5-dichloropyrimidine was obtained as follows: Triethylamine (19.4 ml, 139 mmol), 1-(vinyloxy)butane (18.0 ml, 139 mmol) and palladium(II) acetate (2.08 g, 9.30 mmol) were added to a stirred solution of 2,4,5-trichloropyrimidine (15 ml, 132 mmol) in polyethylene glycol 400 (150 ml). The solution was heated at 80 C. for 2 h. After cooling to 0 C., diethylether was added, the organic layer was separated and washed with brine, dried on MgSO4, filtered and evaporated to afford an orange oil. This oil was dissolved in 300 mL of a petroleum ether/AcOEt mixture (85:15), 40 g of silica was added and this suspension was filtered. The filtrate was evaporated to afford (E)-4-(2-butoxyvinyl)-2,5-dichloropyrimidine (18.0 g, 54%) as an orange oil; NMR spectrum: (CDCl3) 0.97 (t, 3H), 1.41-1.50 (m, 2H), 1.70-1.78 (m, 2H), 4.03 (t, 2H), 6.09 (d, 1H), 8.07 (d, 1H), 8.33 (s, 1H).

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 5750-76-5, 2,4,5-Trichloropyrimidine.

Reference:
Patent; ASTRAZENECA AB; US2010/105655; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 5750-76-5 as follows., 5750-76-5

2,4,5-trichloropyrimidine (6.1 kg)To 2- (isopropylsulfonyl) aniline (950 g, 4.77 mol) and DBU (181 g, 1.19 mol, 0.25 equiv.)The mixture was stirred at 80 C. for 7.5 hours.After cooling to 25 C,n-heptane (1.9 kg) was added,The mixture was stirred for 30 minutes.Cool the mixture to -5 C.Filter and wash with n-heptane (325 g).The crude product is suspended in ethanol (4.5 kg),Stirred at 25 C. for 12 hours, then cooled to 0 C.After filtration, the crude was dried in vacuo,2,5-dichloro-N- (2- (isopropylsulfonyl) phenyl) pyrimidin-4-amine(1.07 kg, 65% yield).

The chemical industry reduces the impact on the environment during synthesis 5750-76-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Novartis AG; Kapferer, Tobias; Gong, Baoqing; Davis, Mark Clinton; Zheng, Xuchun; (72 pag.)JP2019/196359; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The common heterocyclic compound, 7226-23-5, name is 1,3-Dimethyltetrahydropyrimidin-2(1H)-one, molecular formula is C6H12N2O, 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. 7226-23-5

A solution of diisopropylamine (3.4 mL, 24.38 mmol) in dry tetrahydrofuran (21 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7 mL) was cooled to -78 C. under nitrogen and then treated with a 2.5M solution of n-butyllithium in hexanes (9.8 mL, 24.38 mmol). The reaction mixture was stirred at -78 C. for 30 min and then treated dropwise with a solution of (3-bromo-4-methylsulfanyl-phenyl)-acetic acid methyl ester (6.10 g, 22.17 mmol) in dry tetrahydrofuran (21 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7 mL). The resulting reaction mixture was allowed to stir at -78 C. for 1 h, at which time, a solution of iodomethylcyclopentane (5.59 g, 26.60 mmol) in a small amount of dry tetrahydrofuran was added dropwise. The reaction mixture was allowed to warm to 25 C. where it was stirred for 15 h. The reaction mixture was quenched with water (300 mL) and then concentrated in vacuo to remove tetrahydrofuran. The remaining aqueous phase was extracted with ethyl acetate (3*150 mL). The combined organic layers were washed with a saturated aqueous sodium chloride solution (1*200 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 19/1 hexanes/ethyl acetate) afforded 2-(3-bromo-4-methylsulfanyl-phenyl)-3-cyclopentyl-propionic acid methyl ester (4.52 g, 57%) as a light yellow oil: EI-HRMS m/e calcd for C16H21BrO2S (M+) 356.0446, found 356.0435.

The synthetic route of 7226-23-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bizzarro, Fred Thomas; Corbett, Wendy Lea; Grippo, Joseph Francis; Haynes, Nancy-Ellen; Holland, George William; Kester, Robert Francis; Sarabu, Ramakanth; US2001/39344; (2001); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

147118-40-9, 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. 147118-40-9, name is Rosuvastatin methyl ester, molecular formula is C23H30FN3O6S, 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 methyl (6E)-7-{4-(4-flurophenyl)-6-isopropyl-2-[methyl(methyl sulfonyl)amino]pyrimidin-5-yl}(3R,5S)-3,5-dihydroxyhept-6-enoate (2g, 4.04mmol) in 30ml of acetonitrile, 0.25N solution of NaOH (17.7ml; 4.44mmol) was added over a period of 5 minutes at temperature between 26~29¡ãC with stirring. After stirring for 3-4 hours, 30ml tert-butyl methyl ether was added followed by 10ml of water. The layers were separated and organic layer was extracted with 20ml of water. The combined aqueous layers were concentrated by evaporation under reduced pressure to its half volume. To the concentrated aqueous layer, a 1 M solution of CaCl2.2H2O (2.02ml, 2.02mmol) was added drop wise with stirring at 25-28¡ãC. After stirred for 45 minutes, the precipitate formed was filtered and washed with water to get Rosuvastatin Calcium 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. 147118-40-9, Rosuvastatin methyl ester, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNICHEM LABORATORIES LIMITED; WO2006/106526; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia