Trifluoroacetic acid → HCID 49821674, compound

Participants

Reaction Steps

A solution of 2-[(2,5-dichloropyrimidin-4-yl)amino]-N-methylbenzamide (29.7 mg, 0.100 mmol), diethyl(4-aminobenzyl)phosphonate (29.2 mg, 0.120 mmol), TFA (23 uL, 0.30 mmol) and TFE (1.0 mL) was heated at 100° C. for 30 minutes in a microwave reactor. The reaction mixture was then quenched with saturated aqueous sodium bicarbonate (15 mL) and extracted with EtOAc (20 mL). The organic layer was washed with brine (15 mL), dried over anhydrous NaSO4, filtered, and concentrated in vacuo to yield a yellow solid. This material was purified by preparative HPLC (MDP) to afford 12 mg of diethyl{4-[(5-chloro-4-{[2-(methylcarbamoyl)phenyl]amino}pyrimidin-2-yl)amino]benzyl}phosphonate (yield: 24%). 1H NMR (CD3OD, 400 MHz): δ=1.26 (t, J=7.07 Hz, 6H), 2.92 (s, 3H), 3.15-3.24 (m, 2H), 3.99-4.08 (m, 4H), 7.12 (td, J=7.64, 1.14 Hz, 1H), 7.21 (dd, J=8.59, 2.53 Hz, 2H), 7.48 (ddd, J=8.53, 7.26, 1.64 Hz, 1H), 7.55 (d, J=8.08 Hz, 2H), 7.65 (dd, J=7.83, 1.52 Hz, 1H), 8.06 (s, 1H), 8.70 (d, J=8.34 Hz, 1H). MS (ES+): m/z 506.15 [MH+] (TOF, polar).

Provenance & Evidence