Hydrochloric Acid → HCID 59606042, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-9-methyl-6-(3-oxa-8-azabicyclo[3.2.1]oct-8-yl)-9H-purine (620 mg, 2.22 mmol) and TMEDA (498 μL, 3.33 mmol) in THF (11 mL) at −78° C. was added n-BuLi (1.3 mL, 3.33 mmol, 2.5M solution in hexanes). The resulting mixture was warmed to −40° C. and allowed to stir for 30 min before cooling back to −78° C. DMF (517 μL, 6.65 mmol) was added and the resulting mixture was stirred at −78° C. for 30 min then poured onto 1M HCl. The aqueous layer was extracted with EtOAc and the organic phase washed with brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, MeOH:DCM, 0-10%) affording the title compound as a pale yellow solid (500 mg, 73%). 1H NMR (CDCl3, 400 MHz): δ 9.88 (1 H, s), 5.79 (1 H, d, J=6.14 Hz), 5.05 (1 H, d, J=6.84 Hz), 4.05 (3 H, s), 3.80-3.78 (4 H, m), 2.29-2.01 (4 H, m)

Provenance & Evidence