Imidazole → 3-[2-(Imidazol-1-yl)pyrimidin-4-yl]-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-alpha]pyrimidine

Participants

Reaction Steps

A solution of LiHMDS (370 μl) in hexanes (1.0M, 370 μmol) was added to a stirred solution of imidazole (25 mg, 0.37 mmol) and 3-(2-chloropyrimidin-4-yl)-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-α]pyrimidine (from Example 34) (150 mg, 0.37 mmol) in THF (5 ml) at −78° C. under N2. The reaction was allowed to warm slowly to room temperature overnight and was then quenched with NH4Cl solution (10 ml). The organics were extracted with EtOAc (2×25 ml), washed with brine (10 ml) and concentrated under reduced pressure while dry loading onto silica. The residue was purified by column chromatography on silica using 100% EtOAc as the eluent to afford 3-[2-(imidazol-1-yl)pyrimidin-4-yl]-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-α]pyrimidine (73 mg, 45%): 1H NMR (400 MHz, d6-DMSO) δ 10.08 (1H, d, J 7.2), 8.93 (1H, s), 8.85-8.78 (2H, m), 8.13 (1H, d, J 1.1), 8.03 (1H, d, J 5.5), 7.72 (1H, d, J 7.2), 7.21 (1H, s), 1.64 (6H, s), 0.96 (9H, t, J 8.0), 0.65 (6H, q, J 8.0); m/z (ES+) 453 (M+H+).

Provenance & Evidence