(Diethylamino)sulfur trifluoride → HCID 58292905, compound

Participants

Reaction Steps

A solution of diethyl [hydroxy(4-{[4-{[2-(methylcarbamoyl)phenyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)methyl]phosphonate (Example 133, 8.00 mg, 0.014 mmol) and DAST (7 mg, 0.043 mmol) in DCM (3 mL) was stirred at 0° C. for 1 h. The was treated with sat. NaHCO3 (aq) (3 mL). The layers were separated and the aqueous layer was extracted with DCM (3×5 mL). The organic layers were combined, dried over MgSO4, filtered, concentrated, and residue was purified by prep TLC (5% 7 N ammonia in MeOH in DCM) to give 1.5 mg of the desired product (yield: 19%). 1H NMR (CD3OD, 400 MHz): δ=1.24 (t, J=7.6 Hz, 3 H), 1.32 (t, J=7.2 Hz, 3 H), 2.90 (s, 3 H), 4.00-4.17 (m, 4 H), 5.82 (dd, J=7.2, 44.0 Hz, 1 H), 7.20 (dt, J=1.2, 8.4 Hz, 1 H), 7.39 (d, J=8.4 Hz, 2 H), 7.50 (dt, J=2.0, 8.8 Hz, 1 H), 7.64 (dd, J=1.2, 8.0 Hz, 1 H), 7.69 (d, J=8.0 Hz, 2 H), 8.36 (s, 1 H), 8.43 (d, J=7.2 Hz. 1 H). MS (ES+): m/z 556.14 [MH+]. HPLC: tR=1.50 min (UPLC TOF, polar—3 min).

Provenance & Evidence