HCID 1537257, compound → HCID 49872723, compound

Participants

Reaction Conditions

Reaction Steps

3-Amino-5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4(3H)-one (100 mg, 0.383 mmol) was stirred in pyridine (3 mL) at 25° C. 1-Adamantaneacetyl chloride (204.1 mg, 0.96 mmol) was slowly added and the reaction mixture was allowed to stir at 25° C. for 2 hours. The reaction mixture was concentrated to dryness. The resulting material was dissolved in DMSO (3 mL), filtered through a glass microfiber frit and purified by preparative HPLC [Waters XBridge RP18 column, 5 μm, 30×100 mm, flow rate 40 mL/minute, 20-95% gradient of acetonitrile in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide), with UV detection at 254 nm]. Fractions containing the desired product were pooled and concentrated under vacuum to afford the title compound as a white solid (68 mg, 41%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.54-1.70 (m, 12H), 1.92 (br s, 3H), 2.07 (s, 2H), 7.19-7.27 (m, 2H), 7.49-7.56 (m, 2H), 7.62 (s, 1H), 10.90 (br s, 1H); MS (DCI/NH3) m/z 438 (M+H)+. Elemental Analysis calculated for C24H24FN3O2S: C, 65.88; H, 5.53; N, 9.60. Found C, 65.64; H, 5.48; N, 9.55.

Provenance & Evidence