Sodium periodate → Methyl 5-formylpyrazine-2-carboxylate

Temperature

25 °C

A solution of the 5-(2-dimethylamino-vinyl)-pyrazine-2-carboxylic acid methyl ester (415 mg, 2.0 mmol) in tetrahydrofuran and water (10 mL, 1:1) was treated with powdered sodium periodate (1.3 g, 6.07 mmol). The mixture was stirred at 25° C. for 30 min, at which time, thin layer chromatography suggested complete conversion to a product less polar than starting material. The reaction mixture was concentrated in vacuo nearly to dryness, and the residue was partitioned with ethyl acetate (50 mL) and a saturated aqueous sodium bicarbonate solution (25 mL). The aqueous phase was extracted with ethyl acetate (2×50 mL). Each of the organic extracts was washed with a saturated aqueous sodium chloride solution (25 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo to afford the crude aldehyde, 5-formyl-pyrazine-2-carboxylic acid methyl ester (180 mg), as an orange oil which was used without further characterization or purification.

1. concentrationThe reaction mixture was concentrated in vacuo nearly to dryness
2. customthe residue was partitioned with ethyl acetate (50 mL)
3. extractionThe aqueous phase was extracted with ethyl acetate (2×50 mL)
4. washEach of the organic extracts was washed with a saturated aqueous sodium chloride solution (25 mL)
5. dry with materialThe combined organic extracts were dried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD record

ord-2aaa3479c94c4547bfda753fa0cbb9a8

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07132425B2