Sodium Bicarbonate → HCID 66599980, compound

Participants

Reaction Steps

A mixture of 6-(2-fluoropyridin-3-yl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (300 mg, 1002 μmol) and 2-acetamido-5-aminopyridine (Aldrich, St. Louis, Mo.) (152 mg, 1002 μmol) was suspended in THF (2 mL) and treated with LiHMDS (1.0 M in THF, Aldrich, St. Louis, Mo.) (4009 μl, 4009 μmol). The mixture was stirred for 16 h and then poured into saturated aqueous NaHCO3, extracting with EtOAc. Some dark orange insoluble material was observed. The EtOAc extract was dried (MgSO4), filtered and concentrated to give N-(5-(3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-ylamino)pyridin-2-yl)acetamide (324 mg, 75% yield) as an orange solid. 1H NMR (CDCl3, 300 MHz) δ 12.35 (s, 1H), 9.73 (dd, 1H), 9.04 (s, 1H), 8.69 (bs, 1H), 8.37 (s, 1H), 8.35 (dd, 1H), 8.21 (bs, 2H), 8.00 (bs, 1H), 6.96 (dd, 1H), 5.89 (dd, 1H), 4.23 (m, 1H), 3.84 (m, 1H), 2.21 (s, 3H), 2.3-17 (m, 8H); m/z (API-ES) 431, (M+H)+.

Provenance & Evidence