Tag: M.W=300-400

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 302964-08-5, name is 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, the common compound, a new synthetic route is introduced below. 302964-08-5

To a reaction flask, charged 2-((6-chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6- methylphenyl)thiazole-5-carboxamide (20 g), N-(2-hydroxyl ethyl) piperazine (36 g) and n- butanol were added and the reaction mixture was refluxed for 3 hours to 4 hours. The resulting mixture was cooled and charged with phosphoric acid (10 g) and refluxed at a temperature of 50C to 60C. The reaction mixture was stirred for 1 hour at a temperature of 50C to 60C. The mixture obtained was then cooled to 25C to 35C and stirred for 1 hour maintaining the temperature. The resulting reaction mixture was then filtered and washed with methanol. To the reaction mixture charged water (400 mL) was added and further cooled at a temperature of 15C to 20C. Liquid ammonia (20 mL) was slowly added to the reaction mixture maintaining the temperature at 15C to 20C. The reaction mixture was stirred for 1 hour to isolate the product, amorphous dasatinib. The product was filtered, washed with water and dried under vacuum.

The synthetic route of 302964-08-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CIPLA LIMITED; COTTRILL, Emily; RAO, Dharmaraj Ramachandra; MALHOTRA, Geena; PATHI, Srinivas Laxminarayan; PUPPALA, Ravikumar; JAGANNADHAM, Yellanki; CHENNURU, Ramanaiah; (36 pag.)WO2018/78392; (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. 147118-37-4, name is N-(4-(4-Fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide. A new synthetic method of this compound is introduced below., 147118-37-4

Example 10. [262] E-(6-{2-[2-(N-methyl-N-methanesulfonylamino)-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-5-yl]vinyl}-[(4R,6S)-2,2-dimethyl-[1,3]dioxan-4-yl])-N-methoxy-N-methyl-acetamide [263] 2-[(4R,6S)-2,2-dimethyl-6-(1-phenyl-1H-tetrazole-5-sulfonylmethyl)-[1,3]dioxan-4-yl]-N-methoxy-N-methyl-acetamide (5.4 g), N-[4-(4-fluorophenyl)-5-formyl-6-isopropyl-pyrimidin-2-yl]-N-methyl-methanesulfonamide (3.9 g), and tetrahydrofuran (54 mL) were added to a reactor and then the reaction mixture was cooled to -70C. A solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (1M, 15.0 mL) was slowly added to the reaction mixture, the temperature of which was then adjusted to -20?-10C. The reaction mixture was stirred for 1 hours and then 8% sodium bicarbonate solution (100.0 mL) was added under stirring. The separated organic layer was washed with water (100.0 mL) and then concentrated under reduced pressure to obtain E-(6-{2-[2-(N-methyl-N-methanesulfonylamino)-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-5-yl]vinyl}-[(4R,6S)-2,2-dimethyl-[1,3]dioxan-4-yl])-N-methoxy-N-methyl-acetamide as a solid (5 g, yield 80%).[264] 1H-NMR, 400 MHz, CDCl3, ppm : 1.23~1.27(m, 7H), 1.40(s, 3H), 1.50(s, 3H), 2.42~2.80(dd, 2H), 3.20(s, 3H), 3.37(q, 1H), 3.51(s, 3H), 3.57(s, 3H), 3.70(s, 3H), 4.41(m, 2H), 5.44(dd, 1H), 6.49(d, 2H), 7.08(t, 2H), 7.64(q, 2H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,147118-37-4, N-(4-(4-Fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide, and friends who are interested can also refer to it.

Reference:
Patent; YUHAN CORPORATION; JU, Hyun; JOUNG, Sang-Sun; YI, Hyun-Jik; KHOO, Ja-Heouk; LIM, Jong-Chul; KIM, Jae-Gyu; WO2012/2741; (2012); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

147118-37-4, 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 147118-37-4 as follows.

Example 7 Preparation of Compound of Formula (8B2) [0152] [0153] 2.5 g aldehyde compound, 3.6 g chiral diol sulfone (1a-B) and 50 mL THF were taken in round bottom flask at 35 C. under nitrogen atmosphere. The reaction mixture was cooled to -70 C. to -78 C. and treated with 10 g of NaH. The reaction mixture was stirred for 7-8 hours and quenched with ammonium chloride after completion of the reaction as monitored by TLC. The layers were separated at room temperature followed by washing organic layer with saturated sodium 38 mL saturated sodium bicarbonate solution. The organic layer was distilled under vacuum below 50 C. The solid residue 7.1 g was treated with 35 mL methanol and heated at 55 C. for 1 hour, cooled back to 0 C. and stirred for 1 hour. The isolated product was filtered and washed with chilled methanol to obtain 2.8 g compound of Formula (8B2). [0154] The above process can be repeated by using chiral diol sulfone of Formula (1a-A), (1a-C), (1a-D) for preparing the compound of Formula (8B1), (8B3) and (8B4) respectively by replacing the compound of Formula (1a-B).

The chemical industry reduces the impact on the environment during synthesis 147118-37-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Dwivedi, Shriprakash Dhar; Patel, Dhimant Jasubhai; Rupapara, Mahesh Laljibhai; US2013/158263; (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. 302964-08-5, name is 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide. A new synthetic method of this compound is introduced below., 302964-08-5

j00388j A solution of 1 -(2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl)piperazine (300mg, 0.926 mmol) in DMF (7.5 mL) was charged with potassium carbonate (383 mg, 2.77 mmol) and 2-((6-chloro-2-methylpyrimidin-4-yl)amino-N- (2-chloro-6-methylphenyl)thiazole- 5-carboxamide (255 mg, 0.648 mmol). The reaction mixture was heated to 90C in a sealed tube for 14 h. The reaction mixture was diluted with water (10 mL) and extracted with ethylacetate (3 X 30 mL). The combined organic layers were dried over anhydrous Na2504, filtered and concentrated in vacuo resulting in a crude compound which was purified by chromatography on silica gel, eluting with 3-5% methanol in DCMto give 100 mg, 15% yield of the title compound as light yellow solid. ?H NMR (400 MHz, DMSO-d6): oe = 9.89 (d, J= 15.3 Hz, 1H), 8.21 (d, J= 7.7 Hz, 1H), 7.40 (dd, J= 7.5, 2.0 Hz, 1H), 7.21 -7.32 (m, 2H), 6.02 (s, 1H), 5.76 (s, 1H), 3.74- 3.83 (m, 4H), 3.28 – 3.54 (m, 18H), 2.44 (d, J= 4.5 Hz, 3H), 2.23(d, J= 4.7 Hz, 3H), 1.23 (t, J= 4.9 Hz, 2H); MS (ESj: m/z = 645.5, 647.5, 648.5 [M+H]LCMS: tR = 2.88 mm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,302964-08-5, 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, and friends who are interested can also refer to it.

Reference:
Patent; COFERON, INC.; FOREMAN, Kenneth, W.; JIN, Meizhong; WANNER, Jutta; WERNER, Douglas, S.; WO2015/106292; (2015); 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. 934524-10-4, name is 2,4-Dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below., 934524-10-4

To a solution of the 2,4-dichloro-N-tosylpyrrolopyrimidine 3 (1.00 g, 2.92 mmol) in 1,4-dioxane (40 mL) and H2O (10 mL) was added phenylboronic acid (430 mg, 3.50 mmol) and Na2CO3 (620 mg, 5.84 mmol), and the mixture was degassed under argon. To this mixture was added Pd(PPh3)4 (100 mg, 6 mol %) and the reaction mixture was heated at reflux for 1 h, then cooled to room temperature and the solvent was removed in vacuo. The residue was dissolved in EtOAc (50 mL) and washed with H2O (2 * 30 mL), brine (2 * 30 mL), dried, filtered and the solvent was removed in vacuo to give a yellow residue. The residue was purified by flash chromatography (10% EtOAc/Hexanes) and recrystallised from EtOH to give 5d (600 mg, 55%) as a white solid; mp 151-155 C; deltaH (CDCl3): 8.14 (2H, d, J 8.0 Hz), 7.97 (2H, dd, J 6.0, 2.0 Hz), 7.75 (1H, d, J 4.0 Hz), 7.52-7.51 (3H, m), 7.34 (2H, d, J 8.0 Hz), 6.87 (1H, d, J 4.0 Hz), 2.41 (3H, s); deltaC (CDCl3): 160.6, 155.3, 152.9, 146.3, 136.0, 134.2, 131.1, 129.9, 129.0, 128.8, 127.1, 116.3, 104.1, 21.7; m/z (ESI): 384.0 (M[35Cl]H+), 386.0 (M[37Cl]H+); HRMS (ESI): M[35Cl]H+, found 384.0567. C19H15ClN3O2S+ requires 384.0569.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,934524-10-4, 2,4-Dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Article; O’Brien, Nathan J.; Brzozowski, Martin; Buskes, Melissa J.; Deady, Leslie W.; Abbott, Belinda M.; Bioorganic and Medicinal Chemistry; vol. 22; 15; (2014); p. 3879 – 3886;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia