tert-Butyl bromoacetate → HCID 86754363, compound

Participants

Reaction Steps

n-Butyllithium (4.26 mL; 1.6 M in hexane) is added to a mixture of 2,4-di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indole (III, EXAMPLE 2, 2.0 g) in THF (50 mL) at -15°. After 1 hr, t-butyl bromoacetate (1.27 g) in THF (20 mL) is added, and the mixture is stirred for 2 hr at 20-25°. The mixture is partitioned between aqueous sodium bicarbonate and methylene chloride, and the organic layer is dried and concentrated. Chromatography of the crude product (silica gel; hexane/methylene chloride/ethyl acetate (70/25/5) gives the title compound, mp=131-133°; NMR (CDCl3) 7.87, 7.15, 4.92, 3.92, 3.61, 1.96 and 1.43 δ; MS (m/z=421 (M+).

Provenance & Evidence