Sodium Iodide → Ethyl hydrogen (4-{[4-({2-(diethylcarbamoyl)-4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

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A mixture of diethyl (4-{[4-({2-(diethylcarbamoyl)-4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate (Compound 3B, 228 mg, 311 μmol), sodium iodide (158 mg, 1.06 mmol) in pyridine (3.52 ml) was stirred at reflux for 16 hrs then concentrated in vacuo to a solid which was purified by a Teledyne ISCO Combiflash® Rf system [elution gradient: 5%→95% MeOH in water over 25 CV using a C-18 RP column] to yield the desired product (167 mg, 76%). 1H NMR (400 MHz, CD3OD) δ 8.25 (s, 1H), 8.18 (s, 1H), 7.93 (s, 1H), 7.74 (d, J=1.01 Hz, 2H), 7.69 (d, J=7.07 Hz, 1H), 7.55 (s, 1H), 6.99 (br. s., 1H), 6.52 (br. s., 1H), 4.32 (t, J=6.69 Hz, 2H), 3.88 (s, 3H), 3.71-3.80 (m, 2H), 3.59 (t, J=6.06 Hz, 2H), 3.47 (d, J=6.32 Hz, 2H), 3.14-3.23 (m, 2H), 2.85 (d, J=19.96 Hz, 2H), 2.07-2.16 (m, 2H), 1.11 (t, J=6.82 Hz, 6H), 0.90 (br. s., 3H). MS (ESI): m/z 706.80 [M+H]+. UPLC: tR=1.07 min (UPLC-SQD: analytical—2 min).

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