Methyl 2-chloropyrimidine-5-carboxylate (CAS: 287714-35-6) can be used in the preparation of Fimepinostat (CUDC-907) (CAS: 1339928-25-4). Fimepinostat (CUDC-907) has been employed in trials investigating the treatment of lymphoma, solid tumors, breast cancer, multiple myeloma, and NUT midline carcinoma, among others.
Application In Synthesis of [ 287714-35-6 ]
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
A solution of <strong>[59702-07-7]1-<strong>[59702-07-7]methylpiperazin-2-one</strong></strong> (198 mg, 1.74 mmol) in dichloromethane (4.00 mL) was added to a stirred solution of methyl 2-chloropyrimidine-5-carboxylate (300 mg, 1.74 mmol) in dichloromethane (4.70 mL) at 25° C. The resulting solution was stirred at room temperature for 4 h under nitrogen. The reaction mixture was concentrated and dissolved in ethyl acetate (25 ml) and NaOH (50 ml, 1M aqueous solution). The organic layer was washed with ethyl acetate (25 ml). The organic layers were combined and washed with brine (50 ml), dried using MgSO4, filtered and evaporated to dryness to afford methyl 2-(4-methyl-3-oxopiperazin-1-yl)pyrimidine-5-carboxylate (246 mg, 57percent) as a cream solid. 1H NMR (399.9 MHz, DMSO-d6) delta 2.91 (3H, s), 3.44 (2H, t), 3.83 (3H, s), 4.09 (2H, t), 4.35 (2H, s), 8.86 (2H, s). MS: m/z 501 (2MH+)
To a dry flask was added methyl 2-chloropyrimidine-5-carboxylate (17 mg) and THF (5 mL). The mixture was cooled to -780C and a solution of DIBAL-H in hexane (1 M, 1.2 mL) was added slowly. The resulting mixture was stirred at -780C to it overnight, then quenched with saturated aqueous Na2SO4. The solution was filtered. Solvents were removed under reduced pressure to give (2-chloropyrimidin-5-yl)methanol. MS calcd. for [M+H]+ CsH6ClN2O: 145.1; found: 145.1.
A solution of 2-chloropyrimidine-5-carboxylic acid methyl ester (l .Og, 5.8mmol) in THF (30mL), under argon, was cooled to -78°C. To the solution was added a solution of DIBAL-H in DCM (1.0M, 20.3mL, 20.3mmol), slowly over 40min. The reaction was allowed to warm to r. t. before continuing to stir for a further 16 h. A solution of sat. sodium potassium tartrate (lOOmL) was slowly added, followed by EtOAc, and the mixture was stirred vigorously for 2 h. The organic phase was separated then a further portion of EtOAc was added to the aquoues phase before stirring vigorously for lh. The organic phase was removed and the aqueous phase was washed with a mixture of EtOAc and THF (1 :1). All organic fractions were combined and washed with sat. sodium potassium tartrate solution, water, then brine, and dried (MgS04). The solvent was removed in vacuo to afford the title compound: RT = 1.62 min; mlz (ES+) = 145.0 [M+ H]+.
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 25h;
To a solution of 20 (0.5 g, 3.33 mmol) in anhydrous DMF (15 mL) were added K2CO3 (1.382 g, 10.0 mmol) and 2-chloro-pyrimidine-5-carboxylic acid methyl ester (0.575 g, 3.33 mmol) at room temperature. After stirring at room temperature for 25 h, the reaction mixture was cooled to 0 °C diluted with water (20 mL) and acidified to pH 2 using diluted hydrochloric acid. The white precipitate was collected, washed with water and dried to give 0.678 g of 23; mp 117-118 °C.
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 25h;
To a solution of <strong>[1196473-37-6]3H-benzo[c][1,2]oxaborole-1,6-diol</strong> (0.5 g, 3.33 mmol) in anhydrous DMF (15 mL) were added K2CO3 (1.382 g, 10.0 mmol) and 2-chloro-pyrimidine-5-carboxylic acid methyl ester (0.575 g, 3.33 mmol) at room temperature. After stirring at room temperature for 25 h, the reaction mixture was cooled to 0° C. diluted with water (20 mL) and acidified to pH 2 using diluted hydrochloric acid. The white precipitate was collected, washed with water and dried to give 0.678 g of pure product. Mp 117-118° C. 1HNMR (400 MHz, DMSO-d6) delta 9.26 (s, 1H), 9.08 (s, 2H), 7.44-7.57 (m, 2H), 7.31-7.40 (m, 1H), 5.03 (s, 2H), 3.88 (s, 3H). MS (ESI) m/z=287 [M+H]+.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
