Potassium Hydroxide → 9-((3-phenyl-1H-indol-2-yl)methyl)-9H-purin-6-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 9-[3-phenyl-1-(toluene-4-sulfonyl)-1H-indol-2-ylmethyl]-9H-purin-6-ylamine from Example 22 (330 mg, 0.667 mmol) and 2M KOH (1.3 mL) in MeOH (20 mL) was stirred at 70° C. for 5 h. Volatiles were removed under reduced pressure and the resulting residue was diluted with water. The pH of the solution was adjusted to 1 by addition of 1M HCl and then to 8 by addition of a saturated solution of NaHCO3. The aqueous layer was extracted with EtOAc (×3) and the combined organic layers were dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-9% MeOH in DCM) affording 162 as a white solid (102 mg, 45%). LCMS: RT 3.79 min [M+H]+ 341.2. 1H NMR (DMSO, 400 MHz): δ 11.31 (1H, s), 8.16 (1H, s), 8.02 (1H, s), 7.64-7.59 (2H, m), 7.57 (1H, d, J=7.96 Hz), 7.50 (2H, t, J=7.96 Hz), 7.43-7.33 (2H, m), 7.24 (2H, s), 7.16 (1H, t, J=7.50 Hz), 7.07 (1H, t, J=7.50 Hz), 5.59 (2H, s)

Provenance & Evidence