Pyridazine → 4-(Tributylstannyl)pyrimidine

HRID 1359285Notes

Reaction equation

C([Li])CCC.C[C:7]1(C)[CH2:12][CH2:11]C[C:9](C)(C)[NH:8]1.[N:16]1C=CC=CN=1.[CH2:22]([Sn:26](Cl)([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH3:25]>O.O1CCCC1.CCCCCC>[N:8]1[CH:7]=[CH:12][C:11]([Sn:26]([CH2:31][CH2:32][CH2:33][CH3:34])([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:22][CH2:23][CH2:24][CH3:25])=[N:16][CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

58.0 ml of a hexane solution containing 2.52 mol of n-butyllithium was slowly added dropwise into a solution of 200 ml of tetrahydrofuran containing 25.0 mol of 2,2,6,6-tetramethylpiperidine at −30° C. After stirring at 0° C. for 30 minutes, a mixture of 9.1 ml of pyridazine, 46.0 ml of tri-n-butyltin chloride and 100 ml of tetrahydrofuran was slowly added dropwise thereinto at −78° C. After stirring at −78° C. for 4 hours, 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). Then, it was subjected to silica gel chromatography and eluted with hexane/ethyl acetate (10:1) and then with hexane/ethyl acetate (1:1), to give 6.6 g of the target compound.

Workup

additionwas slowly added dropwise
customat −78° C
stirringAfter stirring at −78° C. for 4 hours
extractionextracted with ethyl acetate
washThe organic phase was washed with brine
customthe solvent was removed
washeluted with hexane/ethyl acetate (10:1)
washeluted with hexane/ethyl acetate (10:1)

Sources & evidence

ORD record: ord-b20b76820cb44d158fe2ed2d4de81a7f
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06599917B1

Reaction notes

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