Imidazole → 9-[2-(1-Imidazolyl)ethyl]-2,4-di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indole

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Reaction Steps

A mixture of 9-(2-methanesulfonyloxyethyl)-2,4-di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indole (IX, EXAMPLE4, 0.64 g), imidazole (1.02 g) and xylene (15 mL) is heated at reflux for 3 hr. The xylene is then removed under reduced pressure, and the residue is partitioned between methylene chloride and aqueous sodium bicarbonate. The organic phase is washed with saline, dried over sodium sulfate and concentrated. Chromatography (silica gel, 4% methanol/methylene chloride) gives the title compound, mp=181°-183°; NMR (CDCl3) 7.88, 7.40, 7.14-7.09, 7.01-6.97, 6.82, 4.56-4.54, 4.44-4.42, 3.92, 3.63 and 1.99 δ.

Provenance & Evidence