Tryptamine → [2-(1H-Indol-3-yl)-ethyl]-[2-(6-methyl-pyridin-2-yl)-6-pyridin-3-yl-pyrimidin-4-yl]-amine

Participants

Reaction Steps

A solution of 4-chloro-2-(6-methyl-pyridin-2-yl)-6-pyridin-3-yl-pyrimidine (Intermediate D) (1 eq, 50 mg), 3-(2-aminoethyl)indole (1.0 eq, 28.3 mg) and K2CO3 (1.0 eq, 24.4 mg) in NMP (1 ml) is heated using microwave radiation at 120° C. for 1 hour. After cooling to room temperature, the mixture is partitioned between EtOAc/water and the organic portion is separated, washed with brine, dried (MgSO4) and concentrated in vacuo. The crude residue is purified by flash chromatography on silica eluting with 0-5% MeOH in DCM and the appropriate fractions are combined and concentrated in vacuo. The resulting residue is dissolved in MeOH and loaded onto a SCX-2 cartridge eluting with MeOH followed by 2M NH3 in MeOH. The methanolic ammonia fractions are concentrated in vacuo and the residue is dissolved in DCM and concentrated in vacuo once again. The resulting solid is dried under vacuum to afford the title compound [M+H]+=407.

Provenance & Evidence