Dimethylformamide → HCID 15114440, compound

Temperature

-35 °C

To a stirred solution of 4.85 gm of 2-bromo-5,6-dimethoxypyrazine in 80 ml of dry ether under N2 at -35° C. was added dropwise 14.5 ml of n butyllithium (1.6N in hexanes). After stirring for 0.5 hours at -35° C. 5.74 ml of dry DMF was added dropwise to the reaction mixture. This dark brown homogeneous solution was stirred at -20° C. for 1 hour and at 25° C. for 0.5 hours, then was quenched with an aqueous solution of NH4Cl. The reaction mixture was extracted with methylene chloride, and the organic fractions were washed with water, brine and dried over MgSO4, and filtered and evaporated to give a red oil. Chromatography on a short silica gel column provided the title aldehyde and its hydrate which was used without further purification.

1. stirringThis dark brown homogeneous solution was stirred at -20° C. for 1 hour and at 25° C. for 0.5 hours
2. customwas quenched with an aqueous solution of NH4Cl
3. extractionThe reaction mixture was extracted with methylene chloride
4. washthe organic fractions were washed with water, brine
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. customevaporated
8. customto give a red oil

ORD record

ord-c1625a888fee4e0a904bf299fd3949b0

Source dataset

uspto-grants-1991_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05011847