Tributyltin Chloride → 4-(5-(Tributylstannyl)pyrazin-2-yl)morpholine
Reaction equation
Br[C:2]1[N:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.C([Li])CCC.[CH2:19]([Sn:23](Cl)([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH3:22]>C1COCC1>[CH2:28]([Sn:23]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:24][CH2:25][CH2:26][CH3:27])[C:2]1[N:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1)[CH2:29][CH2:30][CH3:31]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To compound 4-(5-bromopyrazin-2-yl)morpholine (0.25 g) taken in dry THF (5 ml) and cooled to −78° C., n-butyl lithium (0.4 ml, 1M solution in Hexane) was added stirred for 2 hrs at −78° C. To the above reaction mixture tri-n-butyl tin chloride (1.1 mmol) was added drop wise at −78° C. Reaction mixture was stirred at −78° C. for one hour, quenched with saturated ammonium chloride solution and extracted with ethyl acetate (3×15 ml). The organic layer was washed with water (20 ml) followed by brine, dried over anhydrous sodiumsulphate and concentrated using rotary evaporator. The resulting crude was purified by column chromatography to afford 4-(5-(tributylstannyl)pyrazin-2-yl)morpholine as pale yellow color liquid.
Workup
- customReaction mixture
- stirringwas stirred at −78° C. for one hour
- customquenched with saturated ammonium chloride solution
- extractionextracted with ethyl acetate (3×15 ml)
- washThe organic layer was washed with water (20 ml)
- dry with materialdried over anhydrous sodiumsulphate
- concentrationconcentrated
- customevaporator
- customThe resulting crude was purified by column chromatography
Sources & evidence
- ORD record
- ord-138564da4e434f95a0e134d9ef0644ec
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07807676B2
Reaction notes
Loading…