p-Toluenesulfonic acid → (R)-6-(2-chloro-4-iodophenylamino)-N-(2,3-dihydroxypropoxy)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide

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Reaction Steps

(R)-6-(2-chloro-4-iodophenylamino)-N-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide (Example 26, 140 mg, 0.24 mmol, 1 eq) was dissolved in 3 ml of MeOH and 3 ml of THF then p-toluenesulfonic acid (24 mg, 0.5 eq) was added. After stirring at RT for 6 hours the reaction was complete. Evaporation in vacuo, followed by HPLC purification gave the title compound as a white solid. (31 mg, 24%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.89 (s, 3H) 3.21 (s, 3H) 3.28-3.40 (m, 2H) 3.65-3.74 (m, 2H) 3.93 (dd, J=14.15, 6.82 Hz, 1H) 4.61 (t, J=5.68 Hz, 1H) 4.99 (d, J=4.04 Hz, 1H) 7.14 (d, J=8.34 Hz, 1H) 7.70 (dd, J=8.34, 1.77 Hz, 1H) 7.98 (d, J=1.77 Hz, 1H) 12.03 (s, 1H) 12.50 (s, 1H) [M+H] calc'd for C16H18ClIN4O6, 525; found, 525.

Provenance & Evidence