Category: 14248-01-2

Application of 14248-01-2 ,Some common heterocyclic compound, 14248-01-2, molecular formula is C5H5BrN2O, 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.

To a solution of 5-bromo-1-methylpyrimidin-2(1H)-one (S2, 1 equiv) in DMF/H2O (9:1, 10 vol) was added compound S1 (1 equiv), K2CO3(2 equiv), and tetrakis(triphenylphosphine)palladium (0.1 equiv). The reaction mixture was stirred at 90 C. for 5 h and then concentrated under reduced pressure. The remaining residue was purified by column chromatography on silica gel to give compound S3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14248-01-2, its application will become more common.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAK, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (905 pag.)WO2017/35353; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 14248-01-2 ,Some common heterocyclic compound, 14248-01-2, molecular formula is C5H5BrN2O, 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.

Step 2: 5-(4-Amino-3,5-dimethylphenyl)-1-methylpyrimidin-2(1H)-one [0768] The title compound is prepared from 5-bromo-1-methylpyrimidin-2(1H)-one and 2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline following a procedure analogous to that described in Step 2 of Intermediate 62. The mixture is stirred for 12 hours at 70 C. LC (method 9): tR=0.63 min; Mass spectrum (ESI+): m/z=230 [M+H]+.

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. 14248-01-2, 5-Bromo-1-methylpyrimidin-2(1H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Boehringer Ingelheim International GmbH; ECKHARDT, Matthias; FRATTINI, Sara; HAMPRECHT, Dieter; HIMMELSBACH, Frank; LANGKOPF, Elke; LINGARD, Iain; PETERS, Stefan; WAGNER, Holger; US2013/252937; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 14248-01-2 ,Some common heterocyclic compound, 14248-01-2, molecular formula is C5H5BrN2O, 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: 5.1.12 2-[4-({[1-Methyl-4-(2-methylpyridin-4-yl)-1H-pyrazol-3-yl]oxy}methyl)phenyl]quinoline dihydrochloride (13a) Under argon gas atmosphere, to the mixture of 12 (200 mg, 0.45 mmol), 4-bromo-2-methylpyridine (156 mg, 0.91 mmol), and Na2CO3 (144 mg, 1.36 mmol) in DMF (2.0 mL) and water (0.87 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (PdCl2(dppf)·CH2Cl2, 22 mg, 0.027 mmol), and the mixture was stirred at 100 C for 1 h. After cooling at room temperature, the mixture was concentrated in vacuo, and the residue was purified by silica gel column chromatography (0-5% MeOH in CHCl3) to give a free from of the title compound, which was dissolved in MeOH and the mixture was treated with 4 M HCl/EtOAc. The precipitate formed was collected by filtration and washed with Et2O to give 13a (91 mg, 42%) as a colorless solid. 5.1.17 1-Methyl-5-(1-methyl-3-{[4-(quinolin-2-yl)benzyl]oxy}-1H-pyrazol-4-yl)pyrimidin-2(1H)-one dihydrochloride (13f) Compound 13f was prepared from 12 and 5-bromo-1-methylpyrimidin-2(1H)-one in a manner similar to that described for compound 13a, with a yield of 37% as a pale yellow solid. 1H NMR (DMSO-d6) delta 3.55 (s, 3H), 3.75 (s, 3H), 5.40 (s, 2H), 7.64 (m, 3H), 7.83-7.88 (m, 1H), 7.96 (s, 1H), 8.07 (d, 1H, J = 8.1 Hz), 8.16 (d, 1H, J = 8.6 Hz), 8.22 (d, 1H, J = 8.7 Hz), 8.30 (d, 2H, J = 8.4 Hz), 8.60 (d, 1H, J = 8.7 Hz), 8.67 (d, 1H, J = 3.2 Hz), 8.86 (d, 1H, J = 3.2 Hz); MS (ESI) m/z 424 [M+H]+; Anal. Calcd for C25H21N5O2·2HCl·3.3H2O: C, 54.02; H, 5.37; N, 12.60; Cl, 12.76. Found: C, 54.03; H, 5.66; N, 12.46; Cl, 12.44.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14248-01-2, its application will become more common.

Reference:
Article; Hamaguchi, Wataru; Masuda, Naoyuki; Miyamoto, Satoshi; Shiina, Yasuhiro; Kikuchi, Shigetoshi; Mihara, Takuma; Moriguchi, Hiroyuki; Fushiki, Hiroshi; Murakami, Yoshihiro; Amano, Yasushi; Honbou, Kazuya; Hattori, Kouji; Bioorganic and Medicinal Chemistry; vol. 23; 2; (2015); p. 297 – 313;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia