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

HRID 1453200Notes

Reaction equation

HRID 1453200 reaction equation
Cl[CH2:2][C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[NH:6][C:5](=[O:15])[CH:4]=1.[CH:16]1([C:21]2([CH2:29][CH2:30][C:31]3[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=3)[O:26][C:25](=[O:27])[CH2:24][C:23](=[O:28])[CH2:22]2)[CH2:20][CH2:19][CH2:18][CH2:17]1>>[CH:16]1([C:21]2([CH2:29][CH2:30][C:31]3[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=3)[O:26][C:25](=[O:27])[C:24]([CH2:2][C:3]3[N:8]=[C:7]([C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=4)[NH:6][C:5](=[O:15])[CH:4]=3)=[C:23]([OH:28])[CH2:22]2)[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

3

Reactant 2

HCID 160761026-(4-methoxyphenethyl)-6-cyclopentyl-dihydro-3H-pyran-2,4-dioneHCID 1355877906-(Chloromethyl)-2-(pyridin-2-yl)pyrimidin-4-ol

Product 1

HCID 1361525976-([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)-oneYield 11%

Procedure

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.

Sources & evidence

ORD record
ord-993f399a0cb64f5ea492403bb1b33a10
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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