Sodium Iodide → Ethyl hydrogen (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

Participants

Reaction Conditions

Reaction Steps

A solution of {4-[4-(6-bromo-2-methylcarbamoyl-pyridin-3-ylamino)-5-trifluoromethyl-pyrimidin-2-ylamino]-3-methoxy-benzyl}-phosphonic acid diethyl ester (Compound 38D, 610 mg, 0.94 mmol) in pyridine (9.57 mL) was treated with Sodium iodide (847 mg, 5.65 mmol) and heated at 120° C. for 16 hrs overnight. The reaction solution was concentrated in vacuo and purified using a Teledyne ISCO Combiflash® Rf system [5%→95% MeOH in Water over 25 CV] to afford 543 mg of the title compound (93%). 1H NMR (400 MHz, CD3OD) 8.99 (br. s, 1H), 8.80 (d, J=4.6 Hz, 1H), 8.34 (s, 1H), 7.55 (d, J=9.1 Hz, 1H), 7.10 (s, 1H), 6.90 (d, J=8.1 Hz, 1H), 3.83-3.95 (m, 5H), 3.04 (s, 1H), 2.99 (s, 1H), 2.93 (d, J=5.1 Hz, 3H), 1.21 (t, J=7.0 Hz, 3H). MS (ESI): m/z 619.42/621.44 [M+H]+. UPLC: tR=1.24 min (UPLC-TOF: polar—2 min).

Provenance & Evidence