Category: 7752-82-1

7752-82-1 ,Some common heterocyclic compound, 7752-82-1, molecular formula is C4H4BrN3, 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.

c) 6-Bromo-imidazof1w2-alPyrimidine; 50 mmol of 5-bromo-pyrimidin-2-ylamine are dissolved in 200 mi of saturated aqueous sodium hydrogencarbonate solution. 55 mmol of chloroacetaldehyde are added to the reaction mixture and the mixture is stirred for 24 hours at 25C. The mixture is extracted with ethyl acetate (3×300 ml) and the combined extracts are dried over sodium sulphate and evaporated under reduced pressure. Flash chromatography (SiO2 60F) of the residue provides the title compound which is identified on the basis of its Rf-value

According to the analysis of related databases, 7752-82-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SPEEDEL EXPERIMENTA AG; WO2005/90304; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

A common compound: 7752-82-1, name is 5-Bromopyrimidin-2-amine,molecular formula is C4H4BrN3, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below., 7752-82-1

Conditions B (procedure using an in situ prepared boronic or boronate partner, see example 9) The halogenated substrate (1 eq), bis(pinacolato)diboron (1-2 eq), a suitable base (usually potassium acetate (1-6 eq), a suitable palladium catalyst with its ligands (usually Pd(dppf)Cl2.DCM 1-30 mol%) are stirred in a degassed solvent (usually dimethylformamide) at 60-120C for 1-16h under argon. After cooling down to room temperature, the halogenated tricyclic template (3-(7-bromo-imidazo[1,2-a]quinoxalin-4-ylamino)-propan-1-ol or 3-(7-iodo-imidazo[1,2-a]quinoxalin-4-ylamino)-propan-1-ol) (0.5 eq) is added with base (usually an aqueous solution of sodium or potassium carbonate, 1-6 eq) and a suitable palladium catalyst (usually Pd(PPh3)4 1-30 mol%). The resulting mixture is stirred under argon at 60-120C for 2 to 48h. Concentration, partition (water / ethyl acetate), extraction of the aqueous phase (ethyl acetate), reunion of the organic phases, drying over sodium or magnesium sulfate and purification by flash chromatography or prep TLC over silicagel using a suitable eluent (usually a mixture dichloromethane / methanol or cyclohexane / ethyl acetate or dichloromethane / ethyl acetate or dichloromethane / methanol / ammonia) affords the desired compound. The following examples were prepared according to these procedures. The following table provides a summary of the operating conditions. Example 20: 3-{[1-(2-aminopyrimidin-5-yl)-7-(trifluoromethyl)imidazo[1,2-a]quinoxalin-4-yl]amino}propan-1-ol [Show Image] Prepared as mentioned beforehand 1H NMR (DMSO-d6), delta (ppm): 8.45 (s, 2H), 8.05 (t, J = 5.7 Hz, 1 H), 7.82 (s, 1 H), 7.66 (d, J = 8.6 Hz, 1 H), 7.58 (s, 1 H), 7.45 (d, J = 8.6 Hz, 1H), 7.15 (s, 2H), 4.62 (t, J = 5.1 Hz, 1 H), 3.65 (q, J = 6.3 Hz, 2H), 3.54 (q, J = 6.0 Hz, 2H), 1.84 (qt, J = 6.6 Hz, 2H) ESI-MS m/z 404 (M+H)+

With the rapid development of chemical substances, we look forward to future research findings about 7752-82-1.

Reference:
Patent; Mutabilis SA; EP1972629; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.7752-82-1, name is 5-Bromopyrimidin-2-amine, molecular formula is C4H4BrN3, molecular weight is 173.9987, as common compound, the synthetic route is as follows.7752-82-1

c) 6-Bromo-imidazo[1,2-a]pyrimidine; 50 mmol of 5-bromo-pyrimidin-2-ylamine are dissolved in 200 mi of saturated aqueous sodium hydrogencarbonate solution. 55 mmol of chloroacetaldehyde are added to the reaction mixture and the mixture is stirred for 24 hours at 25C. The mixture is extracted with ethyl acetate (3×300 mi) and the combined extracts are dried over sodium sulphate and evaporated under reduced pressure. Flash chromatography (Si02 60F) of the residue provides the title compound which is identified on the basis of its Rf-value.

Statistics shows that 7752-82-1 is playing an increasingly important role. we look forward to future research findings about 5-Bromopyrimidin-2-amine.

Reference:
Patent; SPEEDEL EXPERIMENTA AG; WO2005/90305; (2005); 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. 7752-82-1, name is 5-Bromopyrimidin-2-amine. A new synthetic method of this compound is introduced below., 7752-82-1

To a solution of 2-amino pyridine (30 g, 0.31 mol) in DME (120 mL) was added chloro acetone (40.5 mL, 0.47 mol) at room temperature. The reaction mixture was heated to reflux, and then stirred for 48 hours. The volatiles were concentrated under reduced pressure. Then the residue was purified by column chromatography eluting with 1% MeOH/DCM to afford Int-2 (20 g, 48%) as a liquid. Mass (m/z): 133 [M++1]. 1H NMR (200 MHz, dmso-d6): delta8.05 (d, J=8.2 Hz, 1H), 7.35 (s, 1H), 7.1 (t, J=6.8 Hz, 1H), 6.7 (t, J=6.8 Hz, 1H), 6.5 (d, J=8.2 Hz, 1H), 2.45 (s, 3H). To a solution of Int-2 (10 g, 76.7 mmol) in acetonitrile (50 mL) was added N-iodo succinamide (20.4 g, 80 mmol) portion wise at room temperature and then stirred for 48 hours. The precipitated solid was filtered off. The crude material was re-crystallized from ethyl acetate/water to afford Int-3 (9 g, 49%) as solid. Mass (m/z): 259 [M++1]. 1H NMR (200 MHz, dmso-d6): delta 8.22 (d, J=8 Hz, 1H), 7.47 (d, J=7.2 Hz, 1H), 7.29 (t, J=7.0 Hz, 1H), 2.35 (s, 3H). To a solution of Int-3 (6.0 g, 29.2 mmol) in IPA-H2O (75 mL, 2:1) was added PdCl2(dppf).DCM (4.7 g, 5.8 mmol), followed by the addition of tert-butyl amine (3.1 g, 43.8 mmol) at room temperature and the resulting reaction mixture was degassed for 15 minutes. Then Int-4 (2.9 g, 18.6 mmol) was added to the reaction mixture at room temperature. The reaction mixture was heated to 100 C. and then stirred for 16 hours. The reaction mixture was diluted with water (100 mL), extracted with EtOAc (3¡Á100 mL), washed with water, brine and dried over anhydrous Na2SO4. The organic layer was concentrated under reduced pressure. The crude material was purified by column chromatography eluting with 1% MeOH/DCM to afford Int-5 (1.6 g, 28%). Mass (m/z): 244 [M++1]. 1H NMR (200 MHz, dmso-d6): delta 8.51 (t, J=5 Hz, 2H), 7.71 (s, 1H), 7.63-7.55 (m, 2H), 7.34 (t, J=7 Hz, 1H), 6.94 (t, J=7 Hz, 1H), 2.43 (s, 3H). To a stirred mixture of 5-bromo 2-aminopyrimidine (8 g, 45.97 mmol) in MeOH-CH3CN (200 mL) in a steel bomb were added Pd(CH3CN)2Cl (2.38 g, 9.19 mmol), racemic-BINAP (5.7 g, 9.19 mmol), DIPEA (10.4 mL, 53.7 mmol) at room temperature and then closed the steel vessel tightly. Then CO gas (100 psi) was purged into the steel bomb and the stirring was continued at 120 C. for 45 hours. The reaction mixture was allowed to room temperature. The reaction mixture was filtered through a pad of celite. The celite pad was washed with excess of methanol and the filtrate was concentrated under vacuum. The crude material was purified by column chromatography eluting with 0.75% MeOH/DCM to afford Int-6 (5 g, 71%) as solid. Mass (m/z): 154 [M++1]. 1H NMR (200 MHz, dmso-d6): delta 8.65 (s, 3H), 7.49 (brs, 2H), 3.58 (s, 3H) To a stirred mixture of Int-5 (3 g, 2.34 mmol) and Int-6 (1.8 g, 12.34 mmol) in 1,4-dioxane (90 mL) were added Pd(OAc)2 (279 mg, 1.23 mmol) and Xanthpos (710 mg, 1.23 mmol) followed by cesium carbonate (6 g, 18.5 mmol) at room temperature. The resulting mixture was degassed and stirred at reflux temperature for 30 hours. The reaction mixture was cooled to room temperature and then stirred for 15 minutes. The precipitated solids were filtered off, washed with water (2¡Á10 mL) and dried under vacuum. The crude material was purified by column chromatography eluting with 1.5% MeOH/DCM to afford Int-7 (0.6 g, 13.6%) as solid. Mass (m/z): 361.2 [M++1]. 1H NMR (500 MHz, dmso-d6): delta 10.76 (brs, 1H), 8.97 (s, 2H), 8.56 (d, J=7, 1H), 8.47 (d, J=5.5 Hz, 1H), 8.38 (s, 1H), 7.58 (d, J=9.5 Hz 1H), 7.34-7.29 (m, 2H), 6.99 (t, J=76 Hz, 1H), 3.84 (s, 3H), 2.46 (s, 3H). To a stirred solution of Int-7 (0.5 g, 1.38 mmol) in MeOH-CH3CN (1:2, 25 mL) was added aqueous NH2OH solution (15 mL) at 0 C. After being stirred for 20 minutes at the same temperature, NaOH (0.44 g, 11.10 mmol) in water (1 mL) was added drop wise to the reaction mixture at 0 C. The reaction mixture was warmed to room temperature and stirred for 2 days. The volatiles were concentrated under vacuum and the obtained residue was diluted with water and neutralized to about pH 7 with 2 N HCl at 0 C. The precipitated solids were filtered off, washed with water (2¡Á10 mL) and dried under vacuum to afford the title compound (0.4 g, 80%) as off-white solid. Mass (m/z): 362.1 [M++1]. 1H NMR (200 MHz, dmso-d6): delta 11.2 (bs, 1H), 10.5 (s, 1H), 9.12 (bs, 1H), 8.84 (s, 2H), 8.57 (d, J=7.0 Hz, 1H), 8.45 (d, J=5.0 Hz, 1H), 8.38 (s, 1H), 7.58 (d, J=9.0 Hz, 1H), 7.32 (t, J=7.5 Hz, 1H), 7.25 (d, J=4.0 Hz, 1H), 6.98 (d, J=7.0 Hz, 1H), 2.49 (s, 3H). 13C NMR (125 MHz, dmso-d6): delta 160.7, 157.1, 153.0, 148.7, 144.5, 142.3, 137.9, 125.2, 123.9, 118.8, 118.2, 117.0, 116.6, 112.7, 112.4, 14.3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7752-82-1, 5-Bromopyrimidin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; Melvin, JR., Lawrence S.; Graupe, Michael; Venkataramani, Chandrasekar; US2010/29638; (2010); 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. 7752-82-1, name is 5-Bromopyrimidin-2-amine. A new synthetic method of this compound is introduced below., 7752-82-1

To a stirred solution of 5-bromopyrimidin-2-amine(A39, 1.0 g, 5.74 mmol) in DMF (20 mL) was added ethyl 3-bromo pyruvate(A15, 0.86 mL, 6.89 mmol) . The reaction mixture was Stirred for 16 h at Room temp and then concentrated under reduced pressure. The crude product was triturated with water and washed with n-pentane and dried to afford ethyl 6-bromoimidazo[l,2-a]pyrimidine-2-carboxylate A40 as light brown solid Yield: 1.50 g,(87%). LC-MS m/z : 268.20[M-H]

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7752-82-1, 5-Bromopyrimidin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; JUBILANT BIOSYS LIMITED; VADIVELU, Saravanan; RAJAGOPAL, Sridharan; BURRI, Raghunadha Reddy; GARAPATY, Shivani; SIVANANDHAN, Dhanalakshmi; THAKUR, Manish Kumar; NATARAJAN, Tamizharasan; SWAMY, Indu N; NAGARAJU, Nagendra; KANAGARAJ, Subramaniam; MOHD, Zainuddin; SARKAR, Sayantani; SAMANTA, Swapan Kumar; ., Hariprakash; (284 pag.)WO2019/102494; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

7752-82-1, 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 7752-82-1, name is 5-Bromopyrimidin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

Sodium carbonate (0.636 g, 6.0 mmol) in water (2.0 mL) was added to a mixture of 5- bromopyrimidin-2-amine (0.348 g, 2.0 mmol), [3-(tert-butoxycarbonyl)phenyl]boronic acid (0.533 g, 2.4 mmol) and tetrakis(triphenylphosphine)palladium (69 mg, 0.06 mmol) in ethanol (3.0 mL) and toluene (3.0 mL). The resulting mixture was heated at 120 0C for 3 h. The mixture was diluted with EtOAc and washed with water and brine. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was treated with methanol. The precipitate was filtered and dried to give the product (399 mg, 73.5%). 272.1.

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 7752-82-1, 5-Bromopyrimidin-2-amine.

Reference:
Patent; INCYTE CORPORATION; ZHUO, Jincong; METCALF, Brian; WO2008/64157; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia