Chlorotrimethylsilane → HCID 71084637, compound

Participants

Reaction Steps

To a solution of 2-(but-3-enyloxy)-3-fluoro-5-(pyrimidin-5-yl)benzaldehyde from step 4C (662 mg, 2.43 mmol) in acetonitrile (1.62 ml) and DMF (0.810 ml) was added thiourea (185 mg, 2.43 mmol) and chlorotrimethylsilane (0.311 ml, 2.43 mmol). The resulting mixture was brought to reflux and stirred for 1 h. The reaction mixture was then diluted with EtOAc (10 mL), washed with water (3×2 mL), brine (5 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by silica gel column chromatography (0-80% EtOAc/hexanes) gave the desired product (3.1 mg, 8.44 μmol, 0.35% yield). 1H NMR (500 MHz, methanol-d4) δ 7.63 (d, J=2.1 Hz, 1H), 7.57 (d, J=2.1 Hz, 2H), 6.03 (s, 1H), 5.99 (d, J=10.4 Hz, 1H), 3.12-3.01 (m, J=6.1, 6.1 Hz, 1H), 2.29-2.16 (m, J=4.6 Hz, 1H), 1.82 (d, J=1.2 Hz, 2H), 1.58 (t, J=12.1 Hz, 1H), 1.35 (dd, J=12.5, 3.1 Hz, 1H), 0.62-0.47 (m, 2H), 0.35-0.18 (m, 1H), −0.07-−0.31 (m, 1H). MS (ESI, M+H)+=331.16

Provenance & Evidence