Electric Literature of 852227-86-2, A common heterocyclic compound, 852227-86-2, name is 5-(Chloromethyl)-1,3-dimethyl-1H-pyrazole, molecular formula is C6H9ClN2, 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.
A mixture of 3C (1 g, 3.06 mmol), 5-(chloromethyl)- 1 ,3-dimethyl- 1 H-pyrazole (0.531 g, 3.67 mmol) and cesiumcarbonate (2.99 g, 9.19 mmol) in DMA (12 mL) was stirred at rt for 3 d. The reactionmixture was absorbed onto CELITE and chromatographed on an 80 gm ISCO silica gel cartridge, eluting with a 0-9% MeOH/CH2C12 gradient. The purest fractions wereconcentrated to afford 610 mg of product. The mixed fractions were concentrated to afford 350 mg of material that was triturated with ethyl acetate to afford 155 mg of awhite solid. This was combined with the purest fractions to afford 185A (766 mg, 1.762 mmol, 58% yield) as a yellow solid. ?H NMR (400MHz, DMSO-d6) oe 8.47 (d, J5.1 Hz, 1H), 7.42 (d, J=0.6 Hz, 1H), 7.35 – 7.26 (m, 2H), 5.46 (s, 1H), 5.20 (s, 2H), 3.50 (s, 3H),3.39 (td, J=6.7, 2.5 Hz, 2H), 2.79 (t, J=6.8 Hz, 2H), 2.00 (s, 3H). MS(ESI) m/z 436.3 (M+H).
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HART, Amy C.; PITTS, William J.; MASTALERZ, Harold; GUO, Junqing; BROWN, Gregory D.; (148 pag.)WO2016/100166; (2016); A1;,
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