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

Participants

Reaction Conditions

Reaction Steps

To a solution of LDA (251 ml, 502 mmol) in THF (650 mL) at −20° C. was added SnBu3H (108.5 ml, 402 mmol) dropwise. The mixture was maintained at −20° C. for 15 min, then cooled to −78° C. 2,4-dichloro pyrimidine (50 g, 335 mmol) was added and the reaction was stirred at −78° C. for 5 h. The cooling bath was removed and the reaction was slowly warmed to 0° C. within 30 min. The mixture was poured into 10% NH4Cl at 0° C., and the aqueous layer was extracted with Et2O. The combined organic layers were washed with brine, dried, filtered and concentrated. The residue was purified with silica gel chromatography (eluting with 1% EtOAc in Hex) to give 4-chloro-2-(tributylstannyl)pyrimidine (18.5 g, 24%) as a pale yellow color syrup. MS (ESI, pos. ion) m/z: 405.1 (M+1); 1H-NMR (400 MHz, CDCl3): δ 8.54 (d, J=8 Hz, 1H), 7.17 (d, J=8 Hz, 1H), 1.61-1.54 (m, 6H), 1.37-1.28 (m, 6H), 1.21-1.17 (m, 6H), 0.90 (m, 9H).

Provenance & Evidence