Tag: M.W:100-200

Reference of 1193-21-1, 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 1193-21-1 as follows.

EXAMPLE 8 This example illustrates the preparation of (E)-methyl 2-[2-(4-fluoropyrimidin-6-yloxy)phenyl]-3-methoxypropenoate, an intermediate for the synthesis of compounds of the invention. A mixture of 4,6-dichloropyrimidine (6.50 g), sulphur tetrafluoride (20.8 g) and Arcton 113 (35 ml) was heated at 50 C. with stirring in a 100 ml Monel reactor for 3.3 hours. The temperature was increased to 100 C. over 25 minutes and maintained at 100 C. for a further 3 hours. The temperature was increased to 151 C. over 20 minutes and maintained at 151 C. for 3 hours. The vessel was then allowed to cool to room temperature. The reaction mixture was poured into saturated sodium hydrogen carbonate solution and extracted with dichloromethane. A sticky solid was observed at the interface and was removed by filtration. The layers were then separated. The organic layer was washed with water, and then distilled at atmospheric pressure to remove the dichloromethane. 4,6-Difluoropyrimidine was isolated by distillation in vacuo (50 C./100 mmHg) as a light yellow oil (400 mg; 7.3% yield); 1 H NMR delta: 6.61 (1H, s); and 8.69 (1H, s)ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1193-21-1, its application will become more common.

Reference:
Patent; Imperial Chemical Industries PLC; US5145856; (1992); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 62802-38-4, 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.62802-38-4, name is 5-Bromo-2-fluoropyrimidine, molecular formula is C4H2BrFN2, molecular weight is 176.9745, as common compound, the synthetic route is as follows.

Step 3: A mixture of 1,3-dimethyl-1H-pyrazol-4-amine (453 mg, 4.66 mmol), 5- bromo-2-fluoropyrimidine (750 mg, 4.24 mmol) and DWA (1.62 mL, 21.8 mmol) in DM50 (5 mE) was heated with at 120 C for 2 h. The resulting mixture was cooled to it and quenched with water. The yellow solid was collected via filtration, washed with water, and dried in vacuum oven to give 5-bromo-N-(1,3-dimethyl-1H-pyrazol-4-yl)pyrimidin-2-amine (1.08 g, 99%). LC-MS (ESI) m/z 268, 270 (M+Hjb.

The chemical industry reduces the impact on the environment during synthesis 62802-38-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PLEXXIKON INC.; HOLLADAY, Mark W.; LIU, Gang; (267 pag.)WO2017/19804; (2017); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 62802-42-0, 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.62802-42-0, name is 2-Chloro-5-fluoropyrimidine, molecular formula is C4H2ClFN2, molecular weight is 132.5235, as common compound, the synthetic route is as follows.

Preparation 115 N-[(4aR,7aS)-6-(5-Fluoropyrimidin-2-yl)-7a-phenyl-4,4-a,5,7-tetrahydropyrrolo[3,4d][1,3]thiazin-2-yl]benzamide A solution of N-[(4aR,7aS)-7a-phenyl-4-a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide (250 mg, 0.629 mmol), 5-fluoro-2-chloropyrimidine (167 mg, 1.26 mmol), 1,4-dioxane (10 mL), and triethylamine (318 mg, 3.14 mmol) is stirred at 110 C. for 4 hours. The reaction is cooled, diluted with water and extracted with dichloromethane. The organic layers are combined, dried, filtered, and concentrated under reduced pressure to give a residue. The residue is purified by silica gel flash chromatography, eluting with hexane/ethyl acetate (1:0) to hexane/ethyl acetate (0:1) to give the title compound (0.217 g, 80%). ES/MS (m/e): 434 (M+H).

The chemical industry reduces the impact on the environment during synthesis 62802-42-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Eli Lilly and Company; BECK, James Peter; GREEN, Steven James; LOPEZ, Jose Eduardo; MATHES, Brian Michael; MERGOTT, Dustin James; PORTER, Warren Jaye; RANKOVIC, Zoran; SHI, Yuan; WATSON, Brian Morgan; WINNEROSKI, JR, Leonard Larry; US2013/261111; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 59950-53-7, name is 5-Aminopyrimidine-4-carboxylic acid. A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Aminopyrimidine-4-carboxylic acid

15 g of 5-aminopyrimidine-4-carboxylic acid was addedIn 200 ml of methanol,Add dropwise 10ml thionyl chloride, stirred at room temperature overnight, concentrated,Add 200 ml of toluene, concentrate,Get 18g 5-aminopyrimidine-4-carboxylate.

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, 59950-53-7, 5-Aminopyrimidine-4-carboxylic acid.

Reference:
Patent; Hunan Huateng Pharmaceutical Co., Ltd.; Bu Gonggaofamingren; (4 pag.)CN107176926; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 155-10-2, 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. 155-10-2, name is 4-Amino-2-chloro-5-fluoropyrimidine, molecular formula is C4H3ClFN3, 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.

Example 95 5-Fluoro-N2-[1-(2-phenyl-ethanesulfonyl)-piperidin-4-ylmethyl]-pyrimidine-2,4-diamine EXAMPLE 95 was prepared from C-[1-(2-phenyl-ethanesulfonyl)-piperidin-4-yl]-methylamine and 2-chloro-5-fluoro-pyrimidin-4-ylamine: MS (m+1)=394.5.

According to the analysis of related databases, 155-10-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Claiborne, Christopher F.; Butcher, John W.; Claremon, David A.; Libby, Brian E.; Liverton, Nigel J.; Munson, Peter M.; Nguyen, Kevin T.; Phillips, Brian; Thompson, Wayne; McCauley, John A.; US2002/165241; (2002); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 10070-92-5, 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. 10070-92-5, name is Pyrimidine-5-carbaldehyde. A new synthetic method of this compound is introduced below.

EXAMPLE l N -[3-(cyclopentyloxy)phenyl]-2,2,2-trifluoro-N -(pyrimidin-5-ylmethyl)ethanesulfonamideDiisopropyl azodicarboxylate (0.45 mL, 2.3 mmol) was added dropwise to a stirred solution of 3-aminophenol (250 mg, 2.3 mmol), cyclopentanol (0.25 mL, 2.8 mmol), and triphenylphosphine (600 mg, 2.3 mmol) in tetrahydrofuran (1.4 mL) at 0 0C. After stirring for an additional 12hr at room temperature, the reaction mixture was rotovapped in vacuo to remove volatile solvents. The residue was directly purified via column chromatography on silica gel (eluting 5-50% EPO ethyl acetate/hexanes) to give 157 mg (40%) of [3-(cyclopentyloxy)phenyl]amine as red oil. To a solution of [3-(cyclopentyloxy)phenyl]-amine (157 mg, 0.89 mmol), pyrimidine aldehyde (96 mg, 0.89 mmol) and acetic acid (51 uL, 0.89 mmol) in dichloroethane 3.6 mL) was added sodium triacetoxyborohydride (283 mg, 1.3 mmol) at room temperature. The resulting mixture was stirred for an additional 2hr or until TLC indicated complete conversion. The reaction mixture was then rotovapped in vacuo to remove volatile solvents. The residue was directly purified via column chromatography on silica gel (eluting 15-100% ethyl acetate/hexanes) to give 200 mg (83%) of [3-(cyclopentyloxy)phenyl]- (pyrimidin-5-ylmethyl)amine as brown oil.A solution of 2,2,2-trifluoroethanesulfonyl chloride (0.1 ImL, l.Ommol) was added dropwise to a solution of [3-(cyclopentyloxy)phenyl](pyrimidin-5-ylmethyl)amine (200 mg, 0.74 mmol) in dichloroethane (2.8 mL) and pyridine (1.4 mL) at 00C. The reaction mixture was allowed to gradually warm to room temperature and then stirred at room temperature until TLC indicated completion of reaction. The solution was then rotovapped in vacuo to remove volatile solvents. The residue was directly purified via column chromatography on silica gel (eluting with 0-100% ethyl acetate/dichloromethane) to give N -[3-(cyclopentyloxy)phenyl]-2,2,2-trifluoro-N -(pyrimidin-5- ylmethyl)ethanesulfonamide as a solid. 1H NMR(CDCl3, 500MHz), delta 9.14 (s, IH), 8.61 (s, 2H), 7.29- 7.25 (m, IH), 6.87-6.85 (m, IH), 6.81-6.79 (m, IH), 6.72-6.71 (m, IH), 4.89 (s, 2H), 4.67-4.65 (m, IH), 3.88-3.83 (m, 2H), 1.90-1.61 (m, 8H). MS (ESI): 416 (M+ + H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10070-92-5, Pyrimidine-5-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; WO2006/49968; (2006); A1;,
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. 14080-56-9, name is Thieno[2,3-d]pyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

To a solution of 6-bromo-8-methyl-2H-spiro[imidazo[1 ,5-a]pyridine-3,3?-thietane]-l ,5-dione (prepared according to example 173a, 100 mg, 332 pmol) and thieno[2,3-d]pyrimidin-4- amine (GAS 14080-56-9, 55.2 mg, 365 pmol) in 1 ,4-dioxane (11 mL) was added cesiumcarbonate (20.6 mg, 35.5 pmol) and the mixture was degassed and purged with argon several times. 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene (16.9 mg, 35.5 pmol), 2- (dicyclohexyl-phosphino)-2,4, 6-triisopropylbiphenyl (7.98 mg, 35.5 pmol), palladium(ll)acetate (32.5 mg, 35.5 pmol) and tris(dibenzylideneacetone)dipalladium(0) (325 mg, 996 pmol) were added and the mixture was stirred at 100cC for 2 hours. Themixture was concentrated and the residue purified by flash chromatography (Biotage SNAP cartridge silica 25 g, ethanol: dichloromethane). The isolated product was taken up in ethanol and stirred at RT. The solid was filtered off under vacuo and dried to give 27.0 mg (21% yield) of the title compound.LG-MS: m/z = 372.2 [M÷H].1H-NMR (400 MHz, DMSO-d6) 6 [ppm]= 1.035 (0.63), 1.052 (1.21), 1.070 (0.63), 2.322(0.75), 2.327 (1.01), 2.331 (0.79), 2.447 (16.00), 2.522 (3.03), 2.665 (0.75), 2.669 (0.97),2.673 (0.74), 3.300 (3.97), 4.679 (3.83), 4.705 (3.78), 5.759 (0.60), 7.831 (2.67), 7.846(3.88), 7.908 (3.86), 7.922 (2.65), 8.625 (5.57), 8.699 (6.02), 9.157 (3.44), 10.731 (3.01).

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, 14080-56-9, Thieno[2,3-d]pyrimidin-4-amine.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAYER AKTIENGESELLSCHAFT; KLAR, Ulrich; BOHLMANN, Rolf; SCHAeCKE, Heike; SUeLZLE, Detlev; MENZ, Stephan; PANKNIN, Olaf; (249 pag.)WO2018/134148; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 1193-21-1, name is 4,6-Dichloropyrimidine. A new synthetic method of this compound is introduced below., Safety of 4,6-Dichloropyrimidine

Example 38; Preparation of 4-[6-(4-trifluoromethoxyphenyl)-pyrimidin-4-yl]-benzaldehyde Step 1. 4-Chloro-6-(4-trifluoromethoxy-phenyl)-pyrimidine was prepared by palladium-catalyzed arylation of 4,6-dichloropyrimidine and 4-trifluoromethoxyphenyl boronic acid. 1H NMR (400 MHz, CDCl3) delta 9.05 (s, 1H), 8.14 (d, J=9.8 Hz, 2H), 7.74 (m, 1H), 7.36 (d, J=8.4 Hz, 2H); EIMS 274 m/z (M+).

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, 1193-21-1, 4,6-Dichloropyrimidine.

Reference:
Patent; Dow AgroSciences LLC; US2009/209476; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 4869-46-9, 1,3-Dimethyluracil-5-carboxaldehyde, 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, name: 1,3-Dimethyluracil-5-carboxaldehyde, blongs to pyrimidines compound. name: 1,3-Dimethyluracil-5-carboxaldehyde

General procedure: A mixture of amine 3 (0.1 g, 0.45 mmol) and 5-formyl-N,Ndimethyluracil(17, 0.15 g, 0.9 mmol) in C6H6 was refluxed. When the reaction was finished (TLC monitoring), the mixturewas evaporated. The residue was dissolved in MeOH (1 mL), cooled, treated with NaBH4 (0.22 g, 5.85 mmol), stirred ona magnetic stirrer for 1 h (TLC monitoring), and concentrated. The residue was dissolved in H2O and extracted with CHCl3(5 × 10 mL). The extracts were combined, dried over Na2SO4, and evaporated. The residue was chromatographed over SiO2(eluent EtOAc-hexane, 1:2) to afford 18 (0.1 g, 60%). Amorphous compound, [alpha]D20 -23.0 ( 1.04, CHCl3). Rf 0.5(CHCl3-MeOH, 95:5). C19H25N5O3. IR spectrum (film, nu, cm-1): 3325, 3053, 2935, 2841, 2780, 2740, 2711, 2283, 1701,1663, 1640, 1591, 1565, 1554, 1483, 1458, 1374, 1342, 1274, 1255, 1209, 1183, 1150, 1089, 1041, 1000, 970, 936, 800, 732,699. 1 NMR spectrum (CDCl3, delta, ppm, J/Hz): 1.74 (1H, dtd, J = 12.8, 3.3, 1.2, H-12anti), 1.84 (1H, dtt, J = 12.8, 3.4, 1.7,H-12syn), 2.14 (3H, s, H-1???), 2.22-2.25 (2H, m, H-4ex, H-2ex), 2.43 (1H, m, H-5), 2.84 (1H, ddt, J = 10.6, 3.4, 1.7, H-2en),2.90 (1H, m, H-1), 2.95 (1H, ddt, J = 11.0, 3.4, 1.7, H-4en), 3.36 (3H, s, H-7??), 3.37 (3H, s, H-8??), 3.95 (1H, ddd, J = 15.1, 6.8,1.2, H-6ex), 4.12 (2H, s, H-1?), 4.14 (1H, dt, J = 15.1, 1.2, 1.2, H-6en), 5.47 (1H, br.s, H-2?), 5.95 (1H, d, J = 7.4, H-11), 6.19(1H, d, J = 7.4, H-10), 7.15 (1H, s, H-6??). 13C NMR spectrum (CDCl3, delta, ppm): 26.0 (CH2, C-12), 27.8 (CH, C-5), 27.9 (CH3,C-8??), 34.5 (CH, C-1), 37.1 (CH3, C-7??), 40.0 (CH2, C-1?), 46.3 (CH3, C-1???), 50.2 (CH2, C-6), 62.0 (CH2, C-4), 63.0 (CH2,C-2), 105.3 (CH, C-11), 108.2 (CH, C-10), 110.0 (C, C-5??), 135.4 (C, C-9), 136.4 (C, C-11a), 139.6 (CH, C-6??), 151.7 (C,C-2??), 158.0 (C, C-8), 163.2 (C, C-4??). 15N NMR spectrum (CDCl3, delta, ppm): 29.9 (N-3), 53.3 (N-2?), 122.3 (N-1??), 154.9(N-3??), 168.9 (N-7).

The synthetic route of 4869-46-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tsypysheva; Petrova; Koval?skaya; Lobov; Maksimova; Zainullina; Vinogradova; Vakhitov; Vakhitova, Yu. V.; Galin; Chemistry of Natural Compounds; vol. 54; 5; (2018); p. 938 – 946; Khim. Prir. Soedin.; 5; (2018); p. 794 – 801,8;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 4595-60-2, 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.4595-60-2, name is 2-Bromopyrimidine, molecular formula is C4H3BrN2, molecular weight is 158.984, as common compound, the synthetic route is as follows.

In a 250 round bottom flask was placed butyl lithium (6.1 mL, 2.5 M in hexanes, 15.2 mmol) in THF at -78 C under Ar. To this was added 6 (2.0 g, 12.7 mmol), stirred for 15 min and added Zinc chloride (38.1 mL, 0.5 M in THF, 19.1 mmol). The mixture was warmed up to room temperature and stirred for 1 hr. To this was added 2-bromopyrimidine (2.4 g, 15.2 mmol) and Pd(PPh3J4 (293 mg, 0.252 mmol). The reaction was heated to reflux overnight, cooled to room temperature and filtered. The filtrate was partitioned between brine and ethyl acetate. The organic layer was dried over sodium sulfate and concentrated. The resulting mixture was purified by biotage column chromatography to afford 7AS (936 mg, 54.2%)

Statistics shows that 4595-60-2 is playing an increasingly important role. we look forward to future research findings about 2-Bromopyrimidine.

Reference:
Patent; SCHERING CORPORATION; WO2008/156739; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia