Sodium hydride → HCID 68157559, compound

Participants

Reaction Steps

To a mixture of 9H-purin-6-ylamine (61 mg, 0.454 mmol) in DMF (1 mL) was added NaH (60% in mineral oil, 18 mg, 0.454 mmol) and the suspension was stirred at RT for 10 min under a nitrogen atmosphere. 2-Bromomethyl-1-phenyl-1H-benzoimidazole from Example 5 (0.454 mmol) in DMF (3 mL) was subsequently added and the reaction mixture was stirred at RT for 1 h. The crude reaction mixture was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH. The product containing fractions were combined and concentrated under reduced pressure. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM), then triturated with diethyl ether and purified by preparative HPLC (Phenomenex Gemini 5 μm C18 on a gradient 20-98% 0.1% HCO2H in acetonitrile/water). Crystallization from EtOAc/MeOH afforded 106 as a white solid (10 mg, 6%). LCMS: RT 3.47 min [M+H]+ 342.1. 1H NMR (CDCl3, 400 MHz): δ 8.21 (1H, s), 7.87 (1H, s), 7.84 (1H, d, J=8.01 Hz), 7.48-7.43 (3H, m), 7.36-7.20 (4H, m), 7.12 (1H, d, J=8.03 Hz), 5.57 (2H, s), 5.50 (2H, br)

Provenance & Evidence