Dimethylformamide → HCID 22335225, Verbindung

Temperatur

0 °C

n-Butyllithium (1.6M in hexane, 9 ml, 14.4 mmol) was added to the imidazopyrazine from preparation 79 (2.8 g, 13.13 mmol) in tetrahydrofuran (20 ml) under a nitrogen atmosphere at −78° C. at a rate that maintained the reaction temperature below −70° C. The mixture was warmed to 0° C. and was stirred for 10 minutes and then cooled to −78° C. N,N-Dimethylformamide (1.5 ml, 19.4 mmol) was added dropwise and the mixture was warmed to 0° C. and was stirred for 10 minutes. Saturated sodium hydrogen carbonate solution (40 ml), then water (100 ml) were added and the aqueous solution was extracted with ethyl acetate (100 ml). The organic solution was washed with water (50 ml), then brine (50 ml), dried over magnesium sulphate and evaporated under reduced pressure. The residue was purified by chromatography on silica gel using ethyl acetate in pentane as eluant (gradient from 70:30 to 90:10) to give the title compound as a yellow solid (2.67 g).

1. temperaturemaintained the reaction temperature below −70° C
2. temperaturecooled to −78° C
3. temperaturethe mixture was warmed to 0° C.
4. stirringwas stirred for 10 minutes
5. extractionthe aqueous solution was extracted with ethyl acetate (100 ml)
6. washThe organic solution was washed with water (50 ml)
7. dry with materialbrine (50 ml), dried over magnesium sulphate
8. customevaporated under reduced pressure
9. customThe residue was purified by chromatography on silica gel

ORD-Eintrag

ord-f2d8d1c4354848cbab6291f672d259d5

Quelldatensatz

uspto-grants-2005_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06936619B2