Water → 2-(4-(6-((9-Cyclopentyl-8-fluoro-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)-3-pyridinyl)-1-piperazinyl)ethanol

Participants

Reaction Steps

To compound 248 (0.115 g, 0.19 mmol) in THF (1.0 mL) was added tetrabutylammonium fluoride, 1.0 M in THF (0.49 mL, 0.49 mmol). The reaction was stirred at room temperature. After 1 h, the reaction contents were poured into water. The aqueous layer was brought to pH 12 with 5 N NaOH and extracted with 10% methanol in dichloromethane (3×25 mL). The combined organics were dried with Na2SO4 and concentrated in vacuo. Silica gel chromatography (gradient elution 3 to 7.5% 2M methanolic NH3 in DCM) afforded compound 242 (0.070 g, 75% yield). 1H NMR (500 MHz, DMSO-d6) δ 1.68-1.80 (m, 2 H) 1.92-2.05 (m, 2 H) 2.05-2.17 (m, 2 H) 2.25-2.40 (m, 2 H) 2.45 (t, J=6.11 Hz, 2 H) 2.54-2.62 (m, 4 H) 3.00-3.27 (m, 4 H) 3.54 (q, J=5.95 Hz, 2 H) 4.43 (t, J=5.26 Hz, 1 H) 5.45 (quin, J=9.05 Hz, 1 H) 7.47 (dd, J=9.17, 2.81 Hz, 1 H) 7.93-8.07 (m, 3 H) 8.11 (d, J=9.05 Hz, 1 H) 9.32 (s, 1 H) 9.89 (s, 1 H) ppm.

Provenance & Evidence