2-[2,4-Di(pyrrolidin-1-yl)-5,6,7,8-tetrahydro-9H-pyrimido[4,5-b]indol-9-yl]ethan-1-ol → 2-[2,4-Di(pyrrolidin-1-yl)-9H-pyrimido[4,5-b]indol-9-yl]ethan-1-ol

Participants

Reaction Steps

A mixture of 9-(2-hydroxyethyl)-2,4-di-1-pyrrolidinyl-5,6,7,8-tetrahydro-9H-pyrimido[4,5-b]indole (VII, EXAMPLE2, 5.14 g) and palladium on carbon (10%, 1.4 g) in decalin (250 mL) is heated at reflux for 3 hr. The mixture is cooled to 20°-25°, diluted with methylene chloride (250 mL) and filtered through diatomaceous earth. Removal of the solvent from the filtrate, followed by chromatography (silica gel, 1% methanol/chloroform) of the resulting residue gives the title compound, mp=110°-111; MS (m/z) 351, 323, 307, 296 and 279; NMR (CDCl3) 7.89, 7.23, 7.13, 6.97, 4.38, 4.05, 3.92, 3.62 and 2.0-1.9 δ.

Provenance & Evidence