Electric Literature of 287714-35-6 , The common heterocyclic compound, 287714-35-6, name is Methyl 2-chloropyrimidine-5-carboxylate, molecular formula is C6H5ClN2O2, 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 3b. 2-[2-Chloro-5-(2-chloro-4-methanesulfonyl-benzoylamino)-phenyl]-pyrimidine-5-carboxylic acid methyl ester (compound 1002-7) A mixture of 1001-7 (200 mg, 1.1 mmol), 1-9 (756 mg, 1.6 mmol) and Pd(PPh3)4(60 mg, 0.05 mmol) in saturated NaHCO3 (2 mL) and DMSO (6 mL) was stirred at 100 C. for 3 h. After cooling to room temperature, NaOH (43 mg, 1.1 mmol) was added to reaction solution and stirred for 0.5 h. The reaction mixture was extracted with ethyl acetate. The aqueous layer was adjusted pH to 6 with 1.2 M HCl and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over Na2SO4, concentrated to afford crude acid (300 mg) without further purification. The mixture of the crude acid (300 mg) in MeOH (15 mL) and H2SO4 (0.25 mL) was stirred at 85 C. for 1 h. After removal of solvent, the residue was partitioned between water and ethyl acetate. The combined organic layers were washed with water and brine, dried over Na2SO4. The crude product was purified by column chromatography (hexanes/ethyl acetate: 1/1) to afford compound 1002-7 as a white solid (160 mg, 78% yield via two steps). LCMS: m/z 480.2 [M+1]+. 1H NMR: (400 MHz, CDCl3): delta 3.36 (s, 3H), 3.96 (s, 3H), 7.65 (d, J=8.8 Hz, 1H), 7.81 (dd, J=8.8 Hz, J=2.4 Hz, 1H), 7.93 (d, J=8.0 Hz, 1H), 8.02 (dd, J=8.0 Hz, 1.6 Hz, 1H), 8.14 (d, J=1.2 Hz, 1H), 8.30 (d, J=2.4 Hz, 1H), 9.40 (s, 2H), 11.02 (s, 1H).
The synthetic route of 287714-35-6 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Genetech, Inc.; Curis, Inc.; Cai, Xiong; Qian, Changgeng; Zhai, Haixiao; US2014/18368; (2014); A1;,
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