At the same time, in my other blogs, there are other synthetic methods of this type of compound,74647-39-5, 4-Phenylpyrimidine-2-carboxylic acid, and friends who are interested can also refer to it.
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.74647-39-5, name is 4-Phenylpyrimidine-2-carboxylic acid, molecular formula is C11H8N2O2, molecular weight is 200.19, as common compound, the synthetic route is as follows.name: 4-Phenylpyrimidine-2-carboxylic acid
To a solution of 5-((6-methoxy-7-(3-morpholinopropoxy)quinolin-4-yl)oxy)pyridin- 2-amine (S?, 50 mg, 0.12 mmol), 4-phenylpyrimidine-2-carboxylic acid (19?, 35 mg, 0.17 mmol) in DMF (1 mL), DIEA (100 pL, 74 mg, 0.57 mmol) and HATU (140 mg, 0.37 mmol) were added. The reaction mixture was then allowed to stir at room temperature overnight, but a significant amount of the starting material 2-aminopyridine 5? was detected. Additional equivalents of reagents wre added and the reaction mixture was allowed to stir at room temperature until most of the starting 2-aminopyridine 5? was consumed. The reaction mixture was then diluted with water (20 ml) and extracted with DCM (3 x 10 mL) and the combined organic layer was dried (MgS()4) and concentrated to give a brown residue. Reverse phase chromatography provided 26 mg (36%) ofAr-(5-((6-methoxy-7-(3-morpholinopropoxy)quinolin- 4-yl)oxy)pyridin-2-yl)-4-phenylpyrimidine-2-carboxamide (4) as a white solid. NMR (CDJOD, 300 MHz) d 9.03 (d, J= 5.4 Hz, 1H), 8.72 (d, J = 6.7 Hz, 1H), 8.67 (dd, J= 9.1, 0.7 Hz, 1H), 8.52 (dd, J= 2.9, 0.7 Hz, 1H), 8.40 – 8.30 (m, 2H), 8.20 (d, J= 5.4 Hz, 1H), 7.99 (dd, J = 9.1, 2.9 Hz, i l l). 7.86 (s, 1H), 7.66 – 7.52 (m, 4H), 7.06 (d, J = 6.7 Hz, 1H), 4.43 (t, J= 5.5 Hz, 2H), 4.19 – 4 03 (br s, 21 1). 4.09 (s, 3H), 3.93 – 3.75 (m, 2H), 3.67 (d, J= 12.5 Hz, 2H), 3 49 (t, ./= 7 4 Hz, 2H), 3.28 – 3.13 (m, 2H), 2 45 (p, ,/= 6.4 Hz, 2H) MS m/e: 593 (M+H)7
At the same time, in my other blogs, there are other synthetic methods of this type of compound,74647-39-5, 4-Phenylpyrimidine-2-carboxylic acid, and friends who are interested can also refer to it.
Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; DARWISH, Ihab; YU, Jiaxin; KOLLURI, Rao; HOLLAND, Sacha; (0 pag.)WO2019/231942; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia