Application of 6320-15-6 ,Some common heterocyclic compound, 6320-15-6, molecular formula is C6H7ClN2O2, 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.
Preparatory Example 74 4, 6-Dimethoxy-3- (perfluoroethyl) -1H-pyrazolo [3, 4-d] pyrimidine (Scheme 13) Step 1. 1- (4-Chloro-2, 6-dimethoxypyrimidin-5-yl) -2, 2, 3, 3, 3-pentafluoropropan-1-oneTo a stirred solution of 4-chloro-2, 6-dimethoxypyrimidine (0.50 g, 2.86 mmol) in THF (30 mL) at -30under N2was added 2, 2, 6, 6-tetramethylpiperidinylmagnesium chloride lithium chloride complex (1.5 M in THF, 1.4 mL, 2.86 mmol) dropwise. The reaction solution was stirred at -30for 2 h whereupon a copper (I) cyanide di (lithium chloride) complex solution (1 M in THF, 2.86 mL, 2.86 mmol) was added dropwise. The reaction mixture was stirred for an additional 30 min at -30whereupon 2, 2, 3, 3, 3-pentafluoropropanoic anhydride (1.78 g, 5.7 mmol) was added. The reaction mixture allowed to gradually warm to RT and was stirred for 16 h. The resulting mixture was quenched with sat. aq. sodium bicarbonate (50 mL) , diluted with water (50 mL) and extracted with EtOAc (3 x 50 mL) . The combined organic layers were washed with brine (1 x 30 mL) , dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (0-10ethyl acetate in hexanes) to afford the title compound as an oil.1H NMR (400 MHz, CDCl3) delta: 4.11 (s, 3H) , 4.10 (s, 3H) .
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. 6320-15-6, 4-Chloro-2,6-dimethoxypyrimidine, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO. LTD.; SHEN, Dong-Ming; DWYER, Michael; SINZ, Christopher J.; WANG, Deping; STACHEL, Shawn; PAONE, Daniel; NOMLAND, Ashley; BERGER, Richard; CHEN, Yili; QIAN, Yimin; XU, Shimin; HU, Chunmei; (212 pag.)WO2016/192083; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia