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)thieno[3,2-d]pyrimidin-4(3H)-one

HRID 1453198Notes

Reaction equation

HRID 1453198 reaction equation
Cl[CH2:2][C:3]1[NH:4][C:5](=[O:12])[C:6]2[S:11][CH:10]=[CH:9][C:7]=2[N:8]=1.[Cl:13][C:14]1[C:15]([O:37][CH3:38])=[CH:16][C:17]([O:35][CH3:36])=[C:18]([CH2:20][CH2:21][C:22]2([CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[O:27][C:26](=[O:28])[CH2:25][C:24](=[O:29])[CH2:23]2)[CH:19]=1>>[Cl:13][C:14]1[C:15]([O:37][CH3:38])=[CH:16][C:17]([O:35][CH3:36])=[C:18]([CH2:20][CH2:21][C:22]2([CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[O:27][C:26](=[O:28])[C:25]([CH2:2][C:3]3[NH:4][C:5](=[O:12])[C:6]4[S:11][CH:10]=[CH:9][C:7]=4[N:8]=3)=[C:24]([OH:29])[CH2:23]2)[CH:19]=1

Participants

3

Reactant 2

HCID 167287016-[2-(5-Chloro-2,4-dimethoxy-phenyl)ethyl]-6-cyclopentyl-tetrahydropyran-2,4-dioneHCID 1354161912-(chloromethyl)-3H,4H-thieno[3,2-d]pyrimidin-4-one

Product 1

HCID 1361525862-({6-[2-(5-Chloro-2,4-dimethoxyphenyl)ethyl]-6-cyclopentyl-4-hydroxy-2-oxo-5,6-dihydro-2H-pyran-3-yl}methyl)thieno[3,2-d]pyrimidin-4(3H)-oneYield 20%

Procedure

The title compound was prepared as described in Example B(53), using 2-(chloromethyl)thieno[3,2-d]-pyrimidine-4(3H)-one (Example B(56), 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: 20%. 1H NMR (300 MHz, DMSO-d6) δ 1.24-1.67 (m, 8H), 1.90 (m, 1H), 2.04 (m, 1H), 2.32 (m, 1H), 2.40-2.54 (m, 3H, overlap with DMSO-d5), 2.71 (d, J=18 Hz, 1H), 3.52 (ABQ pattern, J=15 Hz, 2H, overlap with H2O), 3.69 (s, 3H), 3.80 (s, 3H), 6.65 (s, 1H), 6.71 (d, J=5.4 Hz, 1H), 7.05 (s, 1H), 7.96 (d, J=5.4 Hz, 1H), 10.88 (br s, 1H), 12.26 (br s, 1H). LC-MS (APCI) calcd for C27H29ClN2O6S: 544.14; found (M+H+) 544.9 m/z.

Sources & evidence

ORD record
ord-cfc367e7b2254997849e09550a918075
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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