Category: 514854-13-8

Reference of 514854-13-8, 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.514854-13-8, name is 6-Ethyl-5-iodopyrimidine-2,4-diamine, molecular formula is C6H9IN4, molecular weight is 264.07, as common compound, the synthetic route is as follows.

According to a general Sonogahisra coupling procedure, ethyl-iodopyrimidine (0.105 g, 0.4 mmol), CuI (0.028 g, 0.08 mmol, 21 mol %), Pd(PPh3)2Cl2 (0.028 g, 0.04 mmol, 10 mol %) and alkyne 45 (0.123 g, 0.6 mmol) were reacted in DMF/Et3N (1.3 mL each) at 60 C. for 12 h. After the mixture was cooled, dark reddish brown solution was concentrated and the product was purified by flash chromatography (SiO2, 5 g, 2% MeOH/CHCl3) to afford coupled pyrimidine 48 as a pale white powder (0.099 g, 71%) followed by reverse phase flash chromatography (NH2 capped SiO2, 3 g, 100% CH2Cl2, 1% MeOH/CH2Cl2) for biological evaluation: TLC Rf=0.1 (5% MeOH/CH2Cl2); mp 161.3-162.8 C.; 1H NMR (500 MHz, CDCl3) delta 8.84 (s, 2H), 8.62-8.02 (m, 2H), 7.88-7.37 (m, 3H), 5.16 (s, 2H), 4.98 (s, 2H), 4.10 (q, J=7.1 Hz, 1H), 2.67 (q, J=7.6 Hz, 2H), 1.65 (d, J=7.2 Hz, 3H), 1.22 (t, J=7.6 Hz, 3H); 13C NMR (12 MHz, CDCl3) delta 174.1, 164.4, 163.8, 161.1, 156.1, 137.5, 133.9, 130.9, 128.8, 128.3, 99.2, 89.9, 29.9, 28.7, 24.3, 12.7; IR (neat cm-1) 3401, 3312, 3159, 2970, 2933, 2871, 2222, 1623, 1563, 1427, 802, 740, 687; HRMS (ESI, M++H) m/z 345.1817 (calculated for C20H21N6, 345.1822); HPLC (a) tR=6.7 mins, 99.6%, (b) tR=7.6 mins, 99.6%

The chemical industry reduces the impact on the environment during synthesis 514854-13-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Wright, Dennis L.; Anderson, Amy C.; Sormunen, Grant; US2015/225353; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 514854-13-8, 6-Ethyl-5-iodopyrimidine-2,4-diamine, 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, 514854-13-8, blongs to pyrimidines compound. SDS of cas: 514854-13-8

According to general Sonogashira coupling procedure ethyl-iodopyrimidine (0.065 g, 0.25 mmol), CuI (0.009g, 0.049 mmol, 20mol%), Pd(PPh3)2Cl2 (0.017 g, 0.025mmol, 10mol%) and alkyne 17 (0.110 g, 0.374 mmol) were reacted in DMF/Et3N ( 1ml each) at 65C for 12 hrs. After the mixture was cooled, the dark brown solution was concentrated and the product was purified by flash chromatography (SiO2 10 g, 2% MeOH/CHC2) followed by reverse phase flash chromatography (NH2 capped SiO2, CHCl2) to afford coupled pyrimidine 19 as a pale solid (0.085 g, 80%). 1H NMR (500 MHz, CDCl3) delta 7.17 (s, 1H), 7.11 (d, J = 2.15 Hz, 1H), 7.07 (dd, J = 2.19, 8.34 Hz, 1H), 6.97 – 6.93 (m, 2H), 6.92 (d, J = 8.36 Hz, 1H), 5.19 (s, 2H), 4.96 (s, 2H), 4.29 (s, 4H), 4.05 (q, J = 7.06 Hz, 1H), 3.85 (s, 3H), 2.71 (q, J = 7.55 Hz, 2H), 1.61 d, J = 7.1Hz, 3H), 1.24 (t, J = 7.57 Hz, 3H); 13C NMR (125 MHz, CDCl3) delta 173.27, 164.26, 160.61, 160.16, 145.23, 143.63, 143.33, 142.40, 134.53, 120.15, 117.89, 117.52, 115.89, 111.15, 110.64, 101.55, 90.57, 75.40, 64.45, 64.41, 55.34, 33.14, 29.65, 24.71, 12.54; HRMS (DART, MH+) m/z 431.2093 (calculated for C25H27N4O3, 431.2083).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,514854-13-8, its application will become more common.

Reference:
Article; Paulsen, Janet L.; Viswanathan, Kishore; Wright, Dennis L.; Anderson, Amy C.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 5; (2013); p. 1279 – 1284;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 514854-13-8, 6-Ethyl-5-iodopyrimidine-2,4-diamine, 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, 514854-13-8, blongs to pyrimidines compound. Recommanded Product: 6-Ethyl-5-iodopyrimidine-2,4-diamine

General procedure: The alkyne (1.2 eq), iododiaminoethyl pyrimidine (1.0 eq) was dissolved in anhydrous DMF (0.15M) and sonicated under argon. Pd(PPh3)2Cl2 (0.1 eq), CuI (0.21 eq), Et3N (24 eq) were added and again sonicated under argon for 15 minutes. The reaction mixture was heated at 60 C for 12h under argon. The reaction mixture was then concentrated in vacuo before preabsorbing onto a mixture of amine and 25% cysteine preabsorbed silica gel (1:1 /wt) and filterted through a plug of silica gel with 5% MeOH/ CH2Cl2. The collected reaction mixture was concentrated in vacuo, and further purified by preparative HPLC to furnish the final product

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,514854-13-8, its application will become more common.

Reference:
Article; Lombardo; Dayanandan; Keshipeddy; Zhou; Si; Reeve; Alverson; Barney; Walker; Hoody; Priestley; Obach; Wright; Drug Metabolism and Disposition; vol. 47; 9; (2019); p. 995 – 1003;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 514854-13-8 ,Some common heterocyclic compound, 514854-13-8, molecular formula is C6H9IN4, 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.

General procedure: The alkyne (1.2 eq), iododiaminoethyl pyrimidine (1.0 eq) was dissolved in anhydrous DMF (0.15M) and sonicated under argon. Pd(PPh3)2Cl2 (0.1 eq), CuI (0.21 eq), Et3N (24 eq) were added and again sonicated under argon for 15 minutes. The reaction mixture was heated at 60 C for 12h under argon. The reaction mixture was then concentrated in vacuo before preabsorbing onto a mixture of amine and 25% cysteine preabsorbed silica gel (1:1 /wt) and filterted through a plug of silica gel with 5% MeOH/ CH2Cl2. The collected reaction mixture was concentrated in vacuo, and further purified by preparative HPLC to furnish the final product

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. 514854-13-8, 6-Ethyl-5-iodopyrimidine-2,4-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Lombardo; Dayanandan; Keshipeddy; Zhou; Si; Reeve; Alverson; Barney; Walker; Hoody; Priestley; Obach; Wright; Drug Metabolism and Disposition; vol. 47; 9; (2019); p. 995 – 1003;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 514854-13-8 , The common heterocyclic compound, 514854-13-8, name is 6-Ethyl-5-iodopyrimidine-2,4-diamine, molecular formula is C6H9IN4, 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.

General procedure: The alkyne (1.2 eq), iododiaminoethyl pyrimidine (1.0 eq) was dissolved in anhydrous DMF (0.15M) and sonicated under argon. Pd(PPh3)2Cl2 (0.1 eq), CuI (0.21 eq), Et3N (24 eq) were added and again sonicated under argon for 15 minutes. The reaction mixture was heated at 60 C for 12h under argon. The reaction mixture was then concentrated in vacuo before preabsorbing onto a mixture of amine and 25% cysteine preabsorbed silica gel (1:1 /wt) and filterted through a plug of silica gel with 5% MeOH/ CH2Cl2. The collected reaction mixture was concentrated in vacuo, and further purified by preparative HPLC to furnish the final product

The synthetic route of 514854-13-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lombardo; Dayanandan; Keshipeddy; Zhou; Si; Reeve; Alverson; Barney; Walker; Hoody; Priestley; Obach; Wright; Drug Metabolism and Disposition; vol. 47; 9; (2019); p. 995 – 1003;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia