Tributylstannane → 4-Chloro-2-(tributylstannyl)pyrimidine

Participants

Reaction Conditions

Reaction Steps

To a mixture of THF (300 mL) and LDA (100 mL, 20.1 mmol) at −20° C. was added SnBu3H (50 mL, 17.4 mmol) dropwise and stirred for 15 min. The reaction mixture was cooled to −78° C. and treated with 2,4-dichloro pyrimidine (20 g, 134 mmol) portionwise. The reaction mixture was stirred at −78° C. for 5 h with constant stirring under argon atmosphere. The cooling bath was removed and the reaction mixture was warmed up to 0° C. within 30 min. The resulting mixture was poured into 10% NH4Cl aqueous solution, and extracted the compound with Et2O. The organic layer was washed with brine, dried with Na2SO4, filtered, and evaporated. The residue was purified by column chromatography (1% EtOAc: 99% n-Hexane) to obtain 4-Chloro-2-tributylstannanyl-pyrimidine (13 g, 24% yield) as a pale yellow color syrup and 2-Chloro-4-tributylstannanyl-pyrimidine 20a (3 g, 5.5% yield) as a pale yellow color syrup.

Provenance & Evidence