1-Butanol → HCID 178463555, compound

Participants

Reaction Conditions

Reaction Steps

1-(1-Phenyl-1H-benzoimidazol-2-yl)ethylamine from Example 4 (211 mg, 0.89 mmol) and 6-chloro-9H-purine (137 mg, 0.89 mmol) was placed in a sealed tube with n-butanol (1.7 mL) and the solution was heated to 120° C. for 48 h. The cooled suspension was diluted with MeOH/CHCl3 and the resulting solution was loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH and the product eluted with 2M NH3/MeOH. The product was further purified by column chromatography (Si—PCC, gradient 0-6% MeOH in DCM) and then triturated with EtOAc to afford racemic 102 as a cream solid (190 mg, 60%). LCMS: RT 2.99 min [M+H]+ 356.2. 1H NMR (DMSO, 400 MHz): δ 8.18-8.07 (2H, m), 7.94-7.85 (1H, m), 7.71-7.45 (7H, m), 7.27-7.17 (2H, m), 7.11-7.06 (1H, m), 5.52 (1H, br), 1.57 (3H, d, J=6.83 Hz)

Provenance & Evidence