Triethylsilane → (R)-1-(3-ethyl-1,3,4,5-tetrahydropyrazolo[3,4,5-de][1,6]naphthyridin-7-yl)-3-(1-phenylethyl)urea

Participants

Reaction Steps

(R)-1-(3-ethyl-1-trityl-1,3,4,5-tetrahydropyrazolo[3,4,5-de][1,6]naphthyridin-7-yl)-3-(1-phenylethyl)urea (27 mg, 0.045 mmol) was taken in TFA (0.1 mL) and stirred at room temperature for 30 minutes. To the reaction was added triethylsilane (21 uL, 0.128 mmol) and the mixture was stirred for 15 minutes at room temperature before it was heated at 80° C. for 30 minutes. The reaction mixture was concentrated, taken in DCM and washed with aqueous sodium bicarbonate, brine, dried with sodium sulfate and concentrated. Purification of the residue by flash column (0-15% MeOH-DCM) gave (R)-1-(3-ethyl-1,3,4,5-tetrahydropyrazolo[3,4,5-de][1,6]naphthyridin-7-yl)-3-(1-phenylethyl)urea. MS ESI calc'd. for C19H22N6O [M+H]+ 351. found 351. 1H NMR (ppm, 500 MHz, DMSO-d6) δ 7.32 (dd, J=3.4, 7.9, 4H), 7.24-7.14 (m, 1H), 6.40 (s, 1H), 4.90-4.79 (m, 1H), 4.02-3.89 (m, 2H), 3.40 (m, 2H), 3.01 (m, 2H), 1.40 (d, J=6.9, 3H), 1.24 (t, J=9.4, 3H).

Provenance & Evidence