A new synthetic route of

Electric Literature of 14432-12-3, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.14432-12-3, name is 4-Amino-2-chloropyridine, molecular formula is C5H5ClN2, molecular weight is 128.56, as common compound, the synthetic route is as follows.

A solution of 4-amino-2-chloropyridine (1.28 gm, 10 mmol) and di-tert-butyl dicarbonate (2.21 gm, 10.1 mmol) in THF (20 mL) was cooled to 00C and a solution of IM lithium bis(trimethylsilyl)amide in THF ( 20 mL, 20 mmol) was added slowly maintaining the temperature below 00C. The reaction was allowed to warm to room temperature over one hour and then quenched by the addition of 1.5 N aqueous ammonium chloride (15 mL). After stirring for several hours the reaction was extracted into ethyl acetate, washed with brine, the organic layer dried (Na2SO4), filtered and evaporated. The residue was triturated with diethyl ether give pure tert-butyl (2-chloropyridin-4- yl)carbamate. The mother liquors were chromatographed on silica gel eluting with 25 – 45% ethyl acetate/ hexane to afford more product. EPO A solution of tert-butyl (2-chloropyridin-4-yl)carbamate (1.14 gm, 5 mmol) in dry THF (20 mL) was cooled to -700C under an inert atmosphere and 1.7 M t-butyl lithium/pentane (8 mL, 13.5 mmol) was slowly added. The reaction was stirred for two hours and then dry DMF (1.2 mL, 15.5 mmol) was added. The reaction was allowed to slowly warm to room temperature over a three hour period. The reaction mixture was quenched with 3 N HCl (12 mL) and diluted with diethyl ether. The ether layer was washed with aqueous NaHCtheta3, dried (over Na2SO4), filtered and evaporated. The residue was triturated with cold diethyl ether to give pure t-butyl (2-chloro-3-formylrhoyridin-4- yl)carbamate. The mother liquors were chromatographed on silica gel eluting with 15-20% ethyl acetate/hexane to give additional product. 1H-NMR(5OO MHz, CDCI3): deltall.O (IH, br s), 10.52 (IH, s), 8.38 (IH, d, J= 6 Hz), 8.31 (IH, d, J= 6 Hz), 1.54 (9H, s); m/e (m+1): 257.2.

The chemical industry reduces the impact on the environment during synthesis 14432-12-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK & CO., INC.; WO2006/135627; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem