N,N,N',N'-Tetramethylethylenediamine → HCID 131723994, compound

Temperature

0 °C

11.2 ml of a hexane solution containing 2.52 mol of n-butyllithium was slowly added to a solution of 30 ml of tetrahydrofuran containing 4.8 ml of 2,2,6,6-tetramethylpiperidine at −30° C., followed by stirring at 0° C. for 30 minutes. Thereafter, 7.3 ml of N,N,N′,N′-tetramethylethylenediamine was added and then a mixture of 1.74 ml of pyridazine, 10.3 ml of tri-n-butyltin chloride and 10 ml of tetrahydrofuran was slowly added to the mixture at −78° C., followed by stirring at −78° C. for 3 hours, Then, water was added to the reaction solution, and then extracted with ethyl acetate. The organic phase was washed with brine and the solvent was removed. Then, the residue was subjected to NH-silica gel (Fuji Silicia) column chromatography and eluted with hexane/ethyl acetate (10:1), and then subjected to silica gel chromatography and eluted with hexane/ethyl acetate (10:1) and then with hexane/ethyl acetate (1:1), to give 660 mg of the target compound.

1. additionwas slowly added to the mixture at −78° C.
2. stirringby stirring at −78° C. for 3 hours
3. extractionextracted with ethyl acetate
4. washThe organic phase was washed with brine
5. customthe solvent was removed
6. washeluted with hexane/ethyl acetate (10:1)
7. washeluted with hexane/ethyl acetate (10:1)

ORD record

ord-b3dd563a29234fa0ae25e8f2af2a18f8

Source dataset

uspto-grants-2003_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06599917B1