3-Chloro-6-[2-(3-chloro-4-methoxy-phenyl)-ethyl]-6-cyclopentyl-dihydro-pyran-2,4-dione → 6-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyl-4-hydroxy-3-[(6-methyl[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)thio]-5,6-dihydro-2H-pyran-2-one

HRID 1453291Notes

Reaction equation

HRID 1453291 reaction equation
Cl[CH:2]1[C:7](=[O:8])[CH2:6][C:5]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([Cl:24])[CH:17]=2)([CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[O:4][C:3]1=[O:25].[CH3:26][C:27]1[CH:28]=[N:29][C:30]2[N:31]([N:33]=[C:34]([SH:36])[N:35]=2)[CH:32]=1>O>[Cl:24][C:18]1[CH:17]=[C:16]([CH2:15][CH2:14][C:5]2([CH:9]3[CH2:13][CH2:12][CH2:11][CH2:10]3)[O:4][C:3](=[O:25])[C:2]([S:36][C:34]3[N:35]=[C:30]4[N:29]=[CH:28][C:27]([CH3:26])=[CH:32][N:31]4[N:33]=3)=[C:7]([OH:8])[CH2:6]2)[CH:21]=[CH:20][C:19]=1[O:22][CH3:23]

Participants

4

Reactant 2

HCID 688674513-Chloro-6-[2-(3-chloro-4-methoxy-phenyl)-ethyl]-6-cyclopentyl-dihydro-pyran-2,4-dioneHCID 178430151HCID 178430151, compound

Product 1

HCID 587624286-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyl-4-hydroxy-3-[(6-methyl[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)thio]-5,6-dihydro-2H-pyran-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared as described in Example C(70), where 3-chloro-6-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyldihydro-2H-pyran-2,4(3H)-dione was used in place of 3-chloro-6-[2-(5-chloro-2,4-dimethoxyphenyl)ethyl]6-cyclopentyldihydro-2H-pyran-2,4(3H)-dione and 6-methyl[1,2,4]triazolo[1,5-a]pyrimidine-2-thiol was used in place of 6-hydroxy-8-mercaptopurine monohydrate. 1H NMR (500 MHz, DMSO-d6, WET suppression of DMSO-h6 (2.5 ppm) and H2O (3.35 ppm) peak areas) δ 1.52-1.69 (m, 8H) 2.22 (m, 2H) 2.30 (s, 3H) 2.35 (m, 1H) 2.50 (m, 1H, overlap with dmso) 2.62 (m, 1H) 2.73 (d, J=17.6 Hz, 1H) 2.98 (d, J=17.9 Hz, 1H) 3.81 (s, 3H) 7.06 (d, J=8.2 Hz, 1H) 7.24 (dd, J=8.5, 1.9 Hz, 1H) 7.30 (d, J=1.9 Hz, 1H) 8.55 (d, J=1.1 Hz, 1H) 8.67 (d, J=2.2 Hz, 1H). MS (APCI) calcd for C25H27ClN4O4S: 515.03; found M=515.0.

Sources & evidence

ORD record
ord-9bc7702b6d5e4a5884c5b24e2dfad977
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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