Dimethylformamide → HCID 24991567, compound

Participants

Reaction Conditions

Reaction Steps

The product of Example 10B (73 mg, 0.437 mmol) and potassium tert-butoxide (51 mg, 0.454 mmol) were dissolved in dimethyl sulfoxide (2.5 mL) and stirred at 25° C. for 1 hour. 4,6-Dichloropyrimidine (111 mg, 0.743 mmol) was added. The reaction mixture was stirred at 25° C. for 18 hours. The mixture was dissolved in DMF (2 mL), filtered and purified by preparative HPLC [Waters® XTerra RP18 5 μm column, 30×100 mm, flow rate 40 mL/min, 5-95% gradient of acetonitrile in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide) over 22 min, with UV detection at 254 nm]. Fractions containing the desired product were pooled, concentrated under vacuum and then processed as described in Method C to provide the free base. It was then reacted with fumaric acid according to Method H to provide the titled compound: 1H NMR (400 MHz, methanol-D4) δ ppm 1.89-2.01 (m, 2H), 2.18 (br s, 1H), 2.27-2.39 (m, 2H), 2.53 (br s, 2H), 3.55 (br s, 2H), 3.59-3.72 (m, 4H), 5.58 (t, J=3.1 Hz, 1H), 6.68 (s, 2H, C4H4O4), 7.10 (d, J=0.9 Hz, 1H), 8.58 (s, 1H). MS (ESI) m/z=266 (M+H)+.

Provenance & Evidence