6-(4-methoxyphenethyl)-6-cyclopentyl-dihydro-3H-pyran-2,4-dione → 6-([6-Cyclopentyl-4-hydroxy-6-[2-(4-methoxyphenyl)ethyl]-2-oxo-5,6-dihydro-2H-pyran-3-yl}methyl)-2-pyridin-2-ylpyrimidin-4(3H)-one

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Reaction Steps

The title compound was prepared as described in Example B(53), using 6-(chloromethyl)-2-pyridin-2-ylpyrimidin-4(3H)-one in place of 5-(chloromethyl)-1,3-dimethyl-1H-1,2,4-triazole, and using 6-cyclopentyl-6-[2-(4-methoxyphenyl)ethyl]dihydro-2H-pyran-2,4(3H)-dione in place of 6-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyldihydro-2H-pyran-2,4(3H)-dione. Yield: 11%. 1H NMR (300 MHz, DMSO-d6) δ 1.32-1.67 (m, 8H), 1.92 (m, 2H), 2.38 (m, 1H), 2.45-2.52 (m, 2H, overlap with DMSO-d5), 2.60 (d, J=17.7 Hz, 1H), 2.80 (d, J=17.7 Hz, 1H), 3.52 (m, 2H, overlap with H2O), 3.66 (s, 3H, overlap with H2O), 6.07 (s, 3H), 6.68 (d, J=8.4 Hz, 2H), 6.95 (d, J=8.4 Hz, 2H), 7.60 (dd, J=7.5, 4.8 Hz, 1H), 7.93 (td, J=8 Hz, 1.5 Hz, 1H), 8.18 (d, J=8 Hz, 1H), 8.70 (d, J=4.8 Hz, 1H), 10.98 (br s, 1H). LC-MS (APCI) calcd for C29H31N3O5: 501.23; found (M+H+) 502.1 m/z.

Provenance & Evidence