ChemicalBook CAS DataBase List ethyl 6-bromo-3-hydroxy-5-methylpyrazine-2-carboxylate

ethyl 6-bromo-3-hydroxy-5-methylpyrazine-2-carboxylate synthesis

5synthesis methods

Product Name:ethyl 6-bromo-3-hydroxy-5-methylpyrazine-2-carboxylate
CAS Number:1269026-22-3
Molecular formula:C8H9BrN2O3
Molecular Weight:261.07

ETHYL 3-HYDROXY-5-METHYLPYRAZINE-2-CARBOXYLATE

141872-22-2
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ethyl 6-bromo-3-hydroxy-5-methylpyrazine-2-carboxylate

1269026-22-3
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Yield:1269026-22-3 88%

Reaction Conditions:

with N-Bromosuccinimide in N,N-dimethyl-formamide at 0 - 20; for 1 h;Inert atmosphere;

Steps:

207.2 Step 2. Synthesis of ethyl 6-bromo-3-hydroxy-5-methylpyrazine-2-carboxylate

A 500 mL flask was charged with ethyl 3-hydroxy-5-methylpyrazine-2-carboxylate (3 g, 16.4 mmol, 1 equiv) and DMF (65.6 mL) under a nitrogen atmosphere, and the resulting solution was cooled to 0 °C, followed by addition of BS (3.06 g, 17.2 mmol, 1.05 equiv). The resulting mixture was allowed to stir for 1 hour at room temperature, then diluted with water (150 mL) and ethyl acetate (200 mL). The layers were separated, and the resulting organic solution was then washed with water (150 mL), 1/2 saturated brine (2 x 150 mL), and brine (2 x 150 mL) sequentially. The organic solution was then dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford ethyl 6-bromo-3-hydroxy-5-methylpyrazine-2- carboxylate (3.77 g, 14.4 mmol, 88.0%) as a pale yellow solid. 1H NMR (500 MHz, DMSO-i) δ 4.30 (q, J= 7.1 Hz, 2H), 2.49 - 2.41 (br s, 3H), 1.29 (t, J= 7.1 Hz, 3H).

References:

WO2018/13597,2018,A1 Location in patent:Paragraph 0590

609-09-6 Synthesis