Sodium Hydroxide → 5-(3-(4-(isopropylamino)pyrimidin-2-yl)-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(3-(4-(isopropylamino)pyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (400 mg, 0.817 mmol) in p-dioxane (4 mL) was added aq. 10% NaOH (2 mL). The mixture was heated at 100° C. for 2 h. The reaction was quenched with ice cold H2O and the resulting precipitate was filtered, washed with ice cold H2O and dried. The residue was purified with RP-HPLC to 5-(3-(4-(isopropylamino)pyrimidin-2-yl)-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (60 mg, 22%) as an off-yellow solid. MS (ESI, pos. ion) m/z: 335.9 (M+1); 1H-NMR (400 MHz, DMSO-d6): δ 11.77 (d, J=2 Hz, 1H), 9.02 (s, 1H), 8.14-8.07 (m, 2H), 7.65 (dd, J=2, 8.8 Hz, 1H), 7.55 (d, J=8 Hz, 1H), 7.11-7.06 (m, 3H), 6.24 (d, J=8 Hz, 1H), 4.33 (brs, 1H), 1.26 (d, J=6.8 Hz, 6H).

Provenance & Evidence