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ChemicalBook CAS DataBase List 3-METHYLPYRAZINE-2-CARBOXYLIC ACID METHYL ESTER
41110-29-6

3-METHYLPYRAZINE-2-CARBOXYLIC ACID METHYL ESTER synthesis

2synthesis methods
Methanol

67-56-1

3-METHYLPYRAZINE-2-CARBOXYLIC ACID

41110-28-5

3-METHYLPYRAZINE-2-CARBOXYLIC ACID METHYL ESTER

41110-29-6

3-Methylpyrazine-2-carboxylic acid (19.95 g, 144 mmol) was suspended in methanol (500 mL) in a 2L round bottom flask. The suspension was cooled in an ice-water bath, followed by slow dropwise addition of concentrated sulfuric acid (27.3 mL, 506 mmol) over 5 min. The reaction mixture was heated to 80 °C and maintained at this temperature for 5 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and the residue was dissolved in dichloromethane (750 mL). Excess acid was neutralized in small amounts with 5 M aqueous sodium hydroxide solution (200 mL). The aqueous layer was separated and extracted with dichloromethane (250 mL). All organic layers were combined, dried with anhydrous magnesium sulfate, filtered and concentrated to give methyl 3-methylpyrazine-2-carboxylate (16.15 g, 106 mmol, 73% yield). Mass spectral analysis showed m/z = 153 [M + H]+.

-

Yield: 87%

Reaction Conditions:

with sulfuric acid at 0 - 60; for 4 h;Inert atmosphere;

Steps:

A Step A:
Methyl 3-methylpyrazine-2-carboxylate.

To a solution of 3-methylpyrazine-2-carboxylic acid (6 g, 43.4 mmol, 1 equiv) in methanol (60 mL) at 0° C. was added H2SO4 (2.9 mL, 54.3 mmol, 1.25 equiv) dropwise, and the reaction mixture was stirred at 60° C. for 4 h.
The solvent was evaporated, and the residue was dissolved in water (5 ml) and basified with a 10% aq. Na2CO3 solution to pH 12.
The solution was extracted with AcOEt.
The combined organic layers were dried over MgSO4, filtered and the solvents evaporated under vacuum to give the title compound (5.75 g, 37.8 mmol, 87%), which was used in the next step without further purification. 1H NMR (300 MHz, CDCl3) δ 8.61 (s, 1H), 8.51 (s, 1H), 4.01 (s, 3H), 2.85 (s, 3H).

References:

JANSSEN PHARMACEUTICA NV;GELIN, Christine US2020/392155, 2020, A1 Location in patent:Paragraph 0172; 0209-0210

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