The origin of a common compound about 50593-92-5

At the same time, in my other blogs, there are other synthetic methods of this type of compound,50593-92-5, 5-Bromo-2-(methylthio)pyrimidine-4-carboxylic acid, and friends who are interested can also refer to it.

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.50593-92-5, name is 5-Bromo-2-(methylthio)pyrimidine-4-carboxylic acid, molecular formula is C6H5BrN2O2S, molecular weight is 249.09, as common compound, the synthetic route is as follows.Safety of 5-Bromo-2-(methylthio)pyrimidine-4-carboxylic acid

A catalytic amount of N,N-dimethylformamide (2 drops) was added to a stirred suspension of 5-bromo-2-(methylthio)pyrimidine-4-carboxylic acid (2.07 g, 8.33 mmol) and a 2 M solution of oxalyl chloride (21 mL, 0.042 mol) in dichloromethane under nitrogen at r.t. Vigorous effervescence was observed. After 30 min everything had dissolved and the solvent was then evaporated in vacuo. The residue was dissolved in dichloromethane (20 mL) and placed under nitrogen. Triethylamine (2.32 mL, 16.66 mmol) was added to this stirred solution at r.t. followed by 4-aminopyridin-3-yl diethylcarbamodithioate (2.01 g, 8.33 mmol). Everything quickly dissolved with a noticeable exotherm. After 3 h at r.t. tic showed a new major product. The reaction was diluted with dichloromethane (20 mL) and washed with a saturated aqueous solution of sodium hydrogen carbonate (40 mL). The organic layer was separated, dried over sodium sulfate, filtered and the solvent evaporated in vacuo. The residue was purified by flash chromatography (ethyl acetate / hexane 15:85 to 60:40) to yield 4-(5-bromo-2- (methylthio)pyrimidine-6-carboxamido)pyridin-3-yl diethylcarbamodithioate (1.99 g, 51%) as a pale yellow amorphous solid. 1H NMR : delta (CDCl3, 400 MHz) 1.30 (t, J = 7 Hz, 3 H), 1.51 (t, J= 7 Hz, 3 H), 2.60 (s, 3 H), 3.93 – 4.08 (m, 4 H), 8.57 – 8.62 (m, 2 H), 8.69 (d, J = 6 Hz, 1 H), 8.85 (s, 1 H), 10.67 (s, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,50593-92-5, 5-Bromo-2-(methylthio)pyrimidine-4-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN, INC.; WO2006/66172; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia