Trifluoroacetic acid → HCID 68709997, compound

Participants

Reaction Steps

tert-Butyl 4-[(6-{[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]methyl}pyridin-2-yl)oxy]piperidine-1-carboxylate (679 mg, 1.23 mmol) was dissolved in DCM (5 ml) and TFA (1 ml) added. The reaction was stirred at rt. for 40 minutes. DCM (150 ml) and sat. Na2CO3 (aq) (150 ml) were added, the phases separated and the aqueous phase extracted with DCM (150 ml). The combined organics were dried through a phase separator and evaporated in vacuo to yield the title compound as a colorless oil. Yield: 550 mg (99%). 1H NMR (400 MHz, CDCl3) δ 8.29 (s, 1H), 7.63 (m, 2H), 7.55 (dd, 1H, J=8.0 Hz, J=7.4 Hz), 7.48 (s, 1H), 7.42 (m, 2H), 6.95 (d, 1H, J=7.2 Hz), 6.61 (d, 1H, J=8.2 Hz), 5.20 (s, 2H), 4.90 (m, 1H), 3.01 (m, 2H), 2.61 (m, 2H), 1.87 (m, 2H), 1.60-1.46 (m, 3H). 13C NMR (400 MHz, CDCl3) δ 163.2, 157.9, 157.1, 151.6, 151.4, 149.3, 139.8, 135.8, 131.8, 129.6, 127.8, 123.1, 121.0, 115.0, 111.3, 71.9, 50.2, 44.4, 32.6. MS (ESI+) 453.00 (M+1H+)

Provenance & Evidence