Triethylsilane → (R)-1-(3-methoxy-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea

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Reaction Steps

(R)-1-(3-Methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (156 mg, 0.282 mmol) and triethylsilane (0.068 mL, 0.423 mmol) were stirred in TFA (2 mL) at room temperature for 2 h. Saturated NaHCO3 was added and the products extracted into EtOAc (×2). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification of the residue by flash chromatography (0-15% MeOH-EtOAc) gave (R)-1-(3-methoxy-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea. MS ESI calc'd. For C16H17N5O2 [M+1]+ 312. found 312. 1H NMR (500 MHz, DMSO-d6) δ 11.98 (s, 1H), 8.93 (s, 1H), 8.54 (s, 1H), 7.76 (br s, 1H), 7.48 (s, 1H), 7.35-7.31 (m, 4H), 7.25-7.20 (m, 1H), 4.88-4.83 (m, 1H), 3.96 (s, 3H), 1.39 (d, J=6.5 Hz, 3H).

Provenance & Evidence