Reaction Steps
A suspension of 6-(4-chlorophenyl)-3-(4-(2-hydroxy-2-methylpropoxy)-3-methoxy-phenyl)-thieno[3,2-d]pyrimidin-4(3H)-one (100 mg; 0.219 mmol) (Example 82), 3-tert-butoxy-3-oxopropanoic acid (83 uL; 0.538 mmol), diisopropylcarbodiimide (83 uL; 0.538 mmol) and 4-N,N-dimethylaminopyridine (27 mg; 0.219 mmol) in 1 mL of CH2Cl2 was stirred at rt for 17 h. Additional 3-tert-butoxy-3-oxopropanoic acid (83 uL; 0.538 mmol) and diisopropylcarbodiimide (83 uL; 0.538 mmol) were added and the suspension stirred at rt for 3 h. The suspension was diluted with CH2Cl2, filtered and the filtrate washed with 1N HCl, saturated aq. NaHCO3 and brine, dried over anhydrous MgSO4, filtered and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, Hexanes/EtOAc; 100:0 to 1:1 gradient) to afford 104 mg (79%) of the title compound as a beige foam. 1H NMR (CDCl3) δ 1.47 (s, 9H), 1.64 (s, 6H), 3.23 (s, 2H), 3.87 (s, 3H), 4.20 (s, 2H), 6.91 (dd, J=8.24 Hz, 2.20 Hz, 1H), 6.95 (d, J=2.20 Hz, 1H), 7.02 (d, J=8.24 Hz, 1H), 7.44 (d, J=8.24 Hz, 2H), 7.53 (s, 1H), 7.66 (d, J=8.80 Hz, 2H), 8.13 (s, 1H); 13C NMR (CDCl3) δ 23.37, 27.92, 44.04, 56.23, 74.44, 81.83, 82.01, 111.53, 114.75, 119.20, 120.87, 123.22, 127.65, 129.47, 130.51, 131.54, 135.67, 148.19, 149.30, 150.49, 151.63, 156.79, 157.40, 165.85, 166.20; HPLC (Method #1) 4.46 min retention time, (97%); MS (ES): m/z 599 [M+H]+.
