Pyrimidines

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 611-08-5, name is 5-Nitrouracil. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 611-08-5

Preparation of 2,4-dichloro-5-nitropyrimidine. 5-Nitrouracil, was treated with phosphorous oxychloride and N, N- [DIMETHYLANILINE,] according to the procedure of Whittaker (J. Chem. Soc. 1951,1565), to give the title compound, which is also available from City Chemical (West Haven, CT).

With the rapid development of chemical substances, we look forward to future research findings about 611-08-5.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2003/99231; (2003); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 62458-96-2, 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. 62458-96-2, name is 7-Benzyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4(3H)-one. A new synthetic method of this compound is introduced below.

To 7-benzyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4(3H)-one (Step A, 1.50 g, 6.22 mmol) in toluene (25 mL) were sequentially added DIPEA (0.87 mL, 5.0 mmol) and POCl3 (0.70 mL, 7.46 mmol). The contents were heated at 105 C. for 2 hour, cooled to rt, diluted with dichloromethane (100 mL) and stirred with cold aq. sat’d NaHCO3 (150 mL) for 1 h. The dichloromethane layer was dried over sodium sulfate and concentrated under reduced pressure to afford the title compound b (1.61 g) as a dark oil. LCMS [M+H]+ 260.08.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,62458-96-2, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; US2008/275052; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 60025-09-4, 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 60025-09-4 as follows.

To a stirred solution of 1-(3-(pyridin-2-yl)-1,6-naphthyridin-2-yl)ethanamine (15 mg, 0.060 mmol) in butanol (1.5 mL) was added 4-amino-6-chloropyrimidine-5-carbonitrile (9.26 mg, 0.060 mmol) and N-ethyl-N-isopropylpropan-2-amine (20.93 muL, 0.120 mmol). The reaction was heated at 120 C. for 2 h. After this time the reaction was cooled to rt. The resulting precipitate was filtered and washed with hexanes to give racemic 4-amino-6-(((1S,1R)-1-(3-(2-pyridinyl)-1,6-naphthyridin-2-yl)ethyl)amino)-5-pyrimidinecarbonitrile. 1H NMR (400 MHz, chloroform-d) delta ppm 9.33 (1H, s), 8.83 (2H, d, J=5.9 Hz), 8.33 (1H, s), 8.14 (1H, s), 8.02 (1H, d, J=5.9 Hz), 7.93 (1H, td, J=7.7, 1.8 Hz), 7.64 (2H, d, J=7.8 Hz), 7.44 (1H, ddd, J=7.6, 4.9, 1.0 Hz), 6.15 (1H, m), 5.28 (2H, bs), 1.38-1.43 (3H, m). Mass Spectrum (ESI) m/e=251.0. Mass Spectrum (ESI) m/e=369.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,60025-09-4, its application will become more common.

Reference:
Patent; AMGEN INC.; US2010/331306; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 4316-97-6, 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. 4316-97-6, name is 4,6-Dichloro-5-methylpyrimidine. A new synthetic method of this compound is introduced below.

4,6-dichloro-5-methylpyrimidine (0.60g, 3.68mmol) and (3R, 4R) -1- benzyl -N, 4- dimethyl-piperidin-3-amine (0.80g, 3.68 mmol) were dissolved DMF (5mL), was added potassium carbonate (1.02g, 7.36mmol), 70 reaction was stirred overnight under nitrogen.Water was added (100 mL) to quench the reaction, extracted with ethyl acetate (70mL ¡Á 3), the organic phase water (50mL) washed with saturated aqueous sodium chloride solution (50 mL), dried the organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure, performed column chromatography (eluent: PE / EtOAc (v / v) = 1/1), to give the product 1.08g, yield: 85.0%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4316-97-6, 4,6-Dichloro-5-methylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Guangdong East Sunshine Pharmaceutical Co., Ltd.; Liu, Bing; Huang, Jiuzhong; Ren, Xingye; Li, Zhi; Zhang, Yingjun; Zhang, Changchun; (55 pag.)CN105566321; (2016); A;,
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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. 139756-21-1, name is 5-(2-Ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one. A new synthetic method of this compound is introduced below., Application In Synthesis of 5-(2-Ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

Example 1 Preparation of 5-(2-ethoxy-5-chlorosulfonyl)-phenyl-1-methyl-3-n-propyl-1,6-dihydro-7H-pyr azolo[4,3-d]pyrimidine-7-one Chlorosulfuric acid (50ml)was added into a 100ml three-neck flask with a stirrer, 5-(2-ethoxy)-phenyl-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidi ne-7-one (31.2g (0.1mol)) was added in batches under stirring in an ice bath. The reaction was exothermic and was performed for 12 hrs. The reaction solution was slowly poured into icy water (100g), a white solid was separated out, filtered, dried. A white solid (30g)was obtained with a yield of 76%.

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, 139756-21-1, 5-(2-Ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one.

Reference:
Patent; Zhejiang Dade Pharmaceutical Group Co., Ltd.; WANG, Jianping; WANG, Jianguo; EP2666776; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 25193-95-7 ,Some common heterocyclic compound, 25193-95-7, molecular formula is C5H6N2O, 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 stirred solution of pyrimidin-5-ylmethanol (5.00 g, 45.4 mmol) in dichloromethane (125 mL) was added thionyl chloride (9.88 mL, 136 mmol) drop wise at 0 C, and allowed to stirred at room temperature for 2 h. The reaction mixture was analyzed by TLC (50% EtOAc/hexanes) and it showed no starting material. The reaction mixture was concentrated under reduced pressure to afford title compound (4.2 g, 69.3%) as a light brown solid. NMR (400 MHz, DMSO-c/6): delta 9.17 (s, 1 H), 8.91 (s, 2H), 4.85 (s, 2H).

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. 25193-95-7, 5-(Hydroxymethyl)pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; STOLLER, Andre; BIGOT, Aurelien; JUNG, Pierre, Joseph, Marcel; GAGNEPAIN, Julien, Daniel, Henri; RENDINE, Stefano; (155 pag.)WO2019/86474; (2019); A1;,
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Electric Literature 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.

EXAMPLE 21:; 6-(3-f4-(2-terf-Butvl-6-cvclobutvl-pvrimidin-4-vl)-piperazin-1-vn-propoxv)-pyrimidin-4-ol; 1.5 g of 2-tert-Butyl-4-[4-(3-chloro-propyl)-piperazin-1-yl]-6-cyclobutyl-pyrimidine (4.27 mmol), 0.72 g of pyrimidine-4,6-diol (6.4 mmol) and 1.31 g of triethylamine in 30 ml of dimethylformamide were stirred for 16 h at 80C. The mixture was extracted with water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated to dryness. The crude product was purified by chromatography on silica gel using dichloromethane-methanol (1-10%). Fractions containing the product were combined. The solvents were evaporated and the oily residue was treated with acetonitrile. The precipitate was collected by filtration and dried to yield 0.27 g of the title compound.MS (ESI) m/z: 427.2 [M+H]+1H-NMR (DMSO): 5 [ppm] 8.1 (s, 1H), 6.4 (s, 1H), 5.5 (s, 1H), 4.15 (m, 2H), 3.6 (m, 4H), 3.4 (m, 2H), 2.4 (m, 6H), 2.25 (m, 2H), 2.15 (m, 2H), 1.95 (m, 1H), 1.85 (m, 2H), 1.8 (m, 1H), 1.3 (s, 9H).

The synthetic route of 1193-24-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT GMBH & CO. KG; WO2006/15842; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 13316-12-6, Adding some certain compound to certain chemical reactions, such as: 13316-12-6, name is 7-Chlorothiazolo[5,4-d]pyrimidine,molecular formula is C5H2ClN3S, 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 13316-12-6.

A solution of 4-[3-(1-aminoethyl)-5-chloro-2-ethoxy-6-fluorophenyl]pyrrolidin-2-one (30 mg, 0.333 mmol) and 7-chloro[1,3]thiazolo[5,4-d]pyrimidine (25.7 mg, 0.15 mmol) [AK-58025, Ark Pharm] in 1-butanol (6.6 mL) was treated with N,N-diisopropylethylamine (0.052 mL, 0.30 mmol) and heated at 114 C. for 2.5 h. The reaction mixture was then concentrated to a yellow residue. Purification by preparative LCMS (pH 2) afforded the title product (0.033 g, 60%) as a white solid as a mixture of four diastereoisomers. 1H NMR (300 MHz, DMSO-d6) delta 9.30 (s, 1H), 8.78 (d, J=8.4 Hz, 1H), 8.37 (d, J=1.8 Hz, 1H), 7.82 (s, 1H), 7.71 (d, J=8.3 Hz, 1H), 5.91-5.70 (m, 1H), 4.29-4.14 (m, 1H), 4.13-3.96 (m, 1H), 3.95-3.81 (m, 1H), 3.60 (dd, J=9.3, 9.3 Hz, 1H), 3.26 (dd, J=7.8, 7.3 Hz, 1H), 2.42-2.21 (m, 2H), 1.59-1.32 (m, 6H); LCMS calculated for C19H20ClFN5O2S (M+H)+: m/z=436.1. found: 435.9.

According to the analysis of related databases, 13316-12-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INCYTE CORPORATION; Li, Yun-Long; Combs, Andrew P.; US2015/361094; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 308348-93-8, 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. 308348-93-8, name is Methyl 2-aminopyrimidine-5-carboxylate. A new synthetic method of this compound is introduced below.

To a mixture of 2-bromo-1,1-diethoxyethane (100.6 g, 0.5 1 mol) and methyl 2-aminopyrimidine-5-carboxylate (63 g, 0.41 mol) in ethanol (300 mL) was added concentrated HBr (40%) (55 g). The reaction mixture was heated to reflux for 3 h under N?. After cooling to rt, the mixture was further cooled with an ice-water bath. The resulting precipitate was collected by vacuum filtration and dried under vacuum overnight to give the desired product (92 g, 87%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,308348-93-8, its application will become more common.

Reference:
Patent; GENENTECH, INC.; FORMA TM, LLC; BAIR, Kenneth W.; BAUMEISTER, Timm R.; BUCKMELTER, Alexandre J.; CLODFELTER, Karl H.; DRAGOVICH, Peter; GOSSELIN, Francis; GUNZNER-TOSTE, Janet; HAN, Bingsong; LIN, Jian; LIU, Xiongcai; REYNOLDS, Dominic J.; SMITH, Chase C.; WANG, Zhongguo; ZAK, Mark; ZHANG, Yamin; ZHAO, Guiling; ZHENG, Xiaozhang; YUEN, Po-Wai; WO2013/127266; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 26032-72-4, 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 26032-72-4 as follows.

As shown in Figure 3-step i, a mixture of phenylboronic acid (1.22 g),2,4,6-trichloropyrimidine (compound 1011), tetrakis(triphenylphosphine) palladium(O) and 2N sodium carbonate (15 mL) in DME (25 mL) was heated at 80 0C overnight. After cooling to it, addition of water (30 mL), extraction with dichloromethane (3 x 20 mL), drying and evaporation, purification by column chromatography (SiO2, 10-20% ethyl acetate in hexane) afforded the desired product, 6-phenyl-2,4-dichloropyrimidine (compound 1012) (0.544 g). As shown in Figure 3-step ii, compound 1012 (0.34 g) was mixed with (,S)-2-amino-N-(2,2,2- trifluoroethylpropanamide (0.3 g) and diisopropylethylamine (0.63 mL) in isopropanol (5 mL) and the reaction mixture heated at 80 0C overnight. Evaporation gave a residue, which after aqueous workup and purification (SiO2, 20% ethyl acetate/hexane) produced 2-(2- chloro-6-phenyl-pyrimidin-4-ylamino)-nu-(2,2,2-trifluoro-ethyl)propionamide (compound 1013) (0.165 g). As shown in Figure 3-step iii, compound 1013 (29 mg), 5-(4,4,5,5- Tetramethyl-[l,3,2]dioxaborolan-2-yl)-7-(toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidine (compound 1005), PdCl2dppf2 (7 mg), and potassium phosphate (32 mg) were heated in 1,4- dioxane (2 mL) at 80 0C overnight. To the reaction was added aqueous lithium hydroxide solution (2 mL). After heating at 600C for Ih, water (20 mL) was added. Extraction with dichloromethane (3X), drying, evaporation and purification (SiO2, 50-100% ethyl acetate/hexane) gave 3.7 mg of 2-[6-phenyl-2-(7eta-pyrrolo[2,3-d]pyrimidin-5-yl)-pyrimidin- 4-ylamino]-N-(2,2,2-trifluoro-ethyl)-propionamide (compound 18).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,26032-72-4, its application will become more common.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2007/41130; (2007); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia