6-[2-(5-Chloro-2,4-dimethoxy-phenyl)ethyl]-6-cyclopentyl-tetrahydropyran-2,4-dione → 2-({6-[2-(5-Chloro-2,4-dimethoxyphenyl)ethyl]-6-cyclopentyl-4-hydroxy-2-oxo-5,6-dihydro-2H-pyran-3-yl}methyl)-6-methylpyrimidin-4(3H)-one

HRID 1453206Notes

Reaction equation

HRID 1453206 reaction equation
Cl[CH2:2][C:3]1[NH:8][C:7](=[O:9])[CH:6]=[C:5]([CH3:10])[N:4]=1.[Cl:11][C:12]1[C:13]([O:35][CH3:36])=[CH:14][C:15]([O:33][CH3:34])=[C:16]([CH2:18][CH2:19][C:20]2([CH:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)[O:25][C:24](=[O:26])[CH2:23][C:22](=[O:27])[CH2:21]2)[CH:17]=1>>[Cl:11][C:12]1[C:13]([O:35][CH3:36])=[CH:14][C:15]([O:33][CH3:34])=[C:16]([CH2:18][CH2:19][C:20]2([CH:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)[O:25][C:24](=[O:26])[C:23]([CH2:2][C:3]3[NH:8][C:7](=[O:9])[CH:6]=[C:5]([CH3:10])[N:4]=3)=[C:22]([OH:27])[CH2:21]2)[CH:17]=1

Participants

3

Reactant 2

HCID 167287016-[2-(5-Chloro-2,4-dimethoxy-phenyl)ethyl]-6-cyclopentyl-tetrahydropyran-2,4-dioneHCID 1354728582-(Chloromethyl)-6-methylpyrimidin-4-ol

Product 1

HCID 1361525872-({6-[2-(5-Chloro-2,4-dimethoxyphenyl)ethyl]-6-cyclopentyl-4-hydroxy-2-oxo-5,6-dihydro-2H-pyran-3-yl}methyl)-6-methylpyrimidin-4(3H)-oneYield 19%

Procedure

The title compound was prepared as described in Example B(53), using 2-(chloromethyl)-6-methylpyrimidin-4(3H)-one (Example B(54), Step 1) in place of 5-(chloromethyl)-1,3-dimethyl-1H-1,2,4-triazole, and using 6-[2-(5-chloro-2,4-dimethoxyphenyl)ethyl]-6-cyclopentyldihydro-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: 19%. 1H NMR (300 MHz, DMSO-d6) δ 1.25-1.75 (m, 8H), 1.87 (s, m overlap, 4H), 2.05 (m, 1H), 2.36 (m, 1H), 2.43-2.50 (m, 2H, overlap with DMSO-d5), 2.56 (d, J=17.5 Hz, 1H), 2.67 (d, J=17.5 Hz, 1H), 3.48 (m, 2H, overlap with H2O), 3.77 (s, 3H), 3.84 (s, 3H), 5.98 (s, 1H), 6.71 (s, 1H), 7.09 (s, 1H). LC-MS (APCI) calcd for C26H31ClN2O6: 502.19; found (M+H+) 503.0 m/z.

Sources & evidence

ORD record
ord-03ff02d29a614abaa21d68d719d22501
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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