6-Cyclopentyl-6-[2-(3-ethyl-4-hydroxy-phenyl)-ethyl]-dihydro-pyran-2,4-dione → 6-Cyclopentyl-3-(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylmethyl)-6-[2-(3-ethyl-4-hydroxy-phenyl)-ethyl]-4-hydroxy-5,6-dihydro-pyran-2-one

HRID 1453164Notes

Reaction equation

HRID 1453164 reaction equation
[CH:1]1([C:6]2([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([CH2:23][CH3:24])[CH:17]=3)[O:11][C:10](=[O:12])[CH2:9][C:8](=[O:13])[CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:25][C:26]1[CH:31]=[C:30]([CH3:32])[N:29]2[N:33]=[C:34]([CH:36]=O)[N:35]=[C:28]2[N:27]=1>>[CH:1]1([C:6]2([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([CH2:23][CH3:24])[CH:17]=3)[O:11][C:10](=[O:12])[C:9]([CH2:36][C:34]3[N:35]=[C:28]4[N:27]=[C:26]([CH3:25])[CH:31]=[C:30]([CH3:32])[N:29]4[N:33]=3)=[C:8]([OH:13])[CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 99739096-Cyclopentyl-6-[2-(3-ethyl-4-hydroxy-phenyl)-ethyl]-dihydro-pyran-2,4-dioneHCID 236352265,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde

Product 1

HCID 574772356-Cyclopentyl-3-(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylmethyl)-6-[2-(3-ethyl-4-hydroxy-phenyl)-ethyl]-4-hydroxy-5,6-dihydro-pyran-2-one

Procedure

The title compound was prepared by coupling 6-Cyclopentyl-6-[2-(3-ethyl-4-hydroxy-phenyl)-ethyl]-dihydro-pyran-2,4-dione (from Example A(22)) to 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde using the Me2NHBH3 method described in the synthesis of Example B(31). 1H NMR (DMSO-d6): d 0.96 (t, 3H, J=7.4 Hz), 1.30-1.58 (br m, 8H), 1.95 (m, 2H), 2.41 (m, 12H), 2.63 (d, 1H, J=17.5 Hz), 3.61 (d, 1H, J=15.8 Hz), 3.72 (d, 1H, J=15.8 Hz), 6.52 (d, 1H, J=8.1 Hz), 6.74 (m, 2H), 6.93 (s, 1H), 8.84 (s, 1H). Anal. Calcd. For C28H34N4O4.0.5AcOH: C, 66.90; H, 6.97; N, 10.76. Found: C, 66.89; H, 6.97; N, 10.83.

Sources & evidence

ORD record
ord-f80cc9a85d5a4338b49011838f422791
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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