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

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.5M (in cyclohexane) lithium diisopropylamide (mono THF) (9.06 mmol, 6.04 mL) in THF (15 mL) at 0° C. was added tri-n-butyltin hydride (2.34 g, 8.05 mmol) in THF (2 mL) dropwise. The reaction mixture was stirred at 0° C. for 15 minutes, then cooled to −78° C. To this solution was added 2,4-dichloropyrimidine (1 g, 6.71 mmol) in THF (7 mL) dropwise. The reaction mixture was stirred at −78° C. for 3 h, then warmed to 0° C. over 30 min. The reaction was quenched with saturated aqueous ammonium chloride (12 mL) at 0° C., then warmed to room temperature and extracted three times with ethyl acetate. The combined organic layers were dried over Na2SO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (hexanes/DCM eluent) provided the product. LCMS-ESI+ calc'd for C16H30ClN2Sn (M+H+): 405.1; Found: 405.1 (M+H+). 1H NMR (400 MHz, CDCl3) δ 8.53 (dd, J=5.4, 1.3 Hz, 1H), 7.16 (dd, J=5.4, 1.2 Hz, 1H), 1.67-1.49 (m, 6H), 1.38-1.27 (m, 6H), 1.26-1.10 (m, 6H), 0.88 (td, J=7.5, 1.3 Hz, 9H).

Provenance & Evidence