Potassium Phosphate, Tribasic → 6-(3-(trifluoromethoxy)benzyl)-5-(4-chlorobenzyl)-3-(3-hydroxy propyl)-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

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To a mixture of 3-(6-bromo-5-(4-chlorobenzyl)-1-methyl-2,4-dioxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate (See Compound 34, step 2, 80 mg, 0.171 mmol) and 3-(trifluoromethoxy) benzylboronic acid (103 mg, 0.342 mmol) in dioxane (4 mL) was added aq. 2 M K3PO4 (0.8 mL) and Pd(dppf)Cl2 (10 mg). The reaction was degassed with nitrogen (3×) and heated at 85° C. for 3 h, cooled to RT, diluted with water (10 mL) then extracted with EA (2×10 mL). The combined organic layers were dried over Na2SO4 and concentrated to a residue which was purified by Prep HPLC to give 6-(3-(trifluoromethoxy)benzyl)-5-(4-chlorobenzyl)-3-(3-hydroxy propyl)-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (15 mg, 16.5% yield) as a white solid. 1H NMR (CDCl3) δ: 8.63 (s, 1H), 7.33 (t, J=8.0 Hz, 1H), 7.19 (d, J=8.4 Hz, 2H), 7.13 (d, J=8.4 Hz, 1H), 7.06 (d, J=7.6 Hz, 1H), 6.98-6.92 (m, 3H), 4.70 (s, 2H), 4.42-4.40 (m, 1H), 4.05 (s, 2H), 3.94-3.90 (m, 2H), 3.60 (s, 3H), 3.42-3.40 (m, 2H), 1.69-1.64 (m, 2H). LCMS: MH+ 534 and TR=3.262 min.

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