Tributyltin Chloride → 7-([1,2,4]Triazol-1-ylmethyl)-3-tributylstannylimidazo[1,2-alpha]pyrimidine

Participants

Reaction Conditions

Reaction Steps

To a cooled (−78° C.) solution of 3-bromo-7-([1,2,4]triazol-1-ylmethyl)-imidazo[1,2-α]pyrimidine (0.42 g, 1.50 mmol) in tetrahydrofuran (15 ml) was added isopropylmagnesium chloride (0.82 ml of a 2M solution in tetrahydrofuran, 2.37 mmol). Mixture was allowed to warm to −45° C. and stirring at this temperature was continued for 0.5 h. Mixture was recooled to −78° C., tributyltin chloride (0.47 ml, 1.72 mmol) added in a dropwise fashion, stirred for 10 min at −78° C. and then allowed to warm to ambient temperature. This process of Grignard formation with subsequent transmetallation to the stannane intermediate was repeated to encourage completion of the reaction giving 7-([1,2,4]triazol-1-ylmethyl)-3-tributylstannylimidazo[1,2-α]pyrimidine as a solution in tetrahydrofuran (ca. 0.1M); m/z (ES+) 487, 489, 490 (M++H).

Provenance & Evidence