Cesium fluoride → 1-(4-{4-[7-amino-2-(thieno[3,2-d]pyrimidin-7-yl)furo[2,3-c]pyridin-4-yl]-1H-pyrazol-1-yl}piperidin-1-yl)ethanone

Participants

Reaction Conditions

Reaction Steps

A portion of 7-(tributylstannanyl)thieno[3,2-d]pyrimidine (0.030 g, 0.071 mmol) was dissolved in DMF (0.8 mL), and the solution was degassed with nitrogen for 10 min. To this mixture was added 1-{4-[4-(7-amino-2-chlorofuro[2,3-c]pyridin-4-yl)-1H-pyrazol-1-yl]piperidin-1-yl}ethanone (0.017 g, 0.047 mmol), Pd(PPh3)4 (0.0066 g, 0.0057 mmol) and cesium fluoride (0.0241 g, 0.159 mmol). The mixture was heated in a microwave reactor for 30 min at 130° C. Purification by MDP and then ISCO chromatography (0 to 20% methanol:DCM) afforded 0.006 g (30%) of the title compound an off-white solid. 1H NMR (400 MHz, CD3OD): δ 9.53 (s, 1 H), 9.36 (s, 1 H), 8.94 (s, 1 H), 8.15 (s, 1 H), 8.03 (s, 1 H), 7.93 (s, 1 H), 7.91 (br. s., 1 H), 4.72 (d, J=13.1 Hz, 1 H), 4.65-4.54 (m, 2 H), 4.14 (d, J=9.6 Hz, 1 H), 2.90 (dt, J=2.8, 13.0 Hz, 1 H), 2.33-2.22 (m, 2 H), 2.20 (s, 3 H), 2.19-2.11 (m, 1 H), 2.10-1.97 (m, 1 H); MS (ESI): 460.36 [M+H]+.

Provenance & Evidence