Triphenylphosphine → HCID 178429386, compound

Participants

Reaction Steps

To a stirred mixture of 5-(cis-3-hydroxycyclobutyl)-7,7-dimethyl-5H-pyrrolo[2,3-b]pyrazin-6(7H)-one (0.022 g, 0.094 mmol), triphenylphosphine (0.030 g, 0.113 mmol), 2-hydroxybenzothiazole (0.017 g, 0.113 mmol) in THF (2 mL) at 0° C. was added DIAD (0.028 mL, 0.141 mmol). The reaction mixture was stirred at room temperature overnight, concentrated, purified by reverse phase HPLC. The pure fractions were concentrated to minimal H2O, neutralized with saturated aqueous NaHCO3, and the off white solid was collected and dried (18.5 mg, 53.5%). MS (M+1):367.1. 1H NMR (400 MHz, MeOH) δ ppm 8.20 (1 H, d, J=3.1 Hz), 8.15 (1 H, d, J=3.1 Hz), 7.76 (1 H, dd, J=7.9, 0.7 Hz), 7.66 (1 H, d, J=7.6 Hz), 7.39 (1 H, td, J=7.8, 1.3 Hz), 7.19-7.34 (1 H, m), 5.79 (1 H, dt, J=7.0, 3.5 Hz), 5.25-5.42 (1 H, m), 3.40-3.56 (2 H, m), 2.68-2.86 (2 H, m), 1.38-1.50 (6 H, m). MS (M+1):367.1.

Provenance & Evidence