Potassium Carbonate → HCID 89629975, compound

Participants

Reaction Steps

A solution of ethyl 4-{3-[(3-chloro-1,2,4-thiadiazol-5-yl)amino]phenyl}-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (75 mg, 0.14 mmol) in TFA (1.0 mL) was stirred for 1 hour. The reaction mixture was then concentrated under reduced pressure and the residue dissolved in ethyl acetate (2.0 mL). Potassium carbonate (2.0 mL, 4.0 mmol) was added and the reaction mixture was allowed to stir for 1 hour. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (×3). The combined organic fractions were washed with water, dried with sodium sulfate, filtered and concentrated under reduced pressure. Purification of the residue by MPLC (0-10% methanol-dichloromethane) gave ethyl 4-{3-[(3-chloro-1,2,4-thiadiazol-5-yl)amino]phenyl}-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate. LRMS (ESI) calc'd for C7H14ClN6O2S [M+H]+: 401, found 401. 1H NMR (600 MHz, DMSO-D6) δ 13.0 (s, 1H), 11.4 (s, 1H), 8.94 (s, 1H), 8.35 (s, 1H), 7.81 (s, 1H), 7.63 (d, 1H, J 7.63 Hz), 7.53 (t, 1H, J=7.62 Hz), 7.39 (d, 1H, J=7.63 Hz), 3.85 (q, 2H, J=7.04 Hz), 0.85 (t, 3H, J=7.04 Hz).

Provenance & Evidence