Diisopropyl Ether → 3-(4-Isopropoxyphenyl)-2-methyl-5-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-6-propylpyrimidin-4(3h)-one potassium salt

HRID 1673756Notes

Reaction equation

[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:16](=[O:17])[C:15]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[C:31]4[NH:35][C:34](=[O:36])[O:33][N:32]=4)=[CH:21][CH:20]=3)=[C:14]([CH2:37][CH2:38][CH3:39])[N:13]=[C:12]2[CH3:40])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].C(OC(C)C)(C)C.C(OCC)(=O)CCCCC.[K:58]>C(O)C>[K:58].[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:16](=[O:17])[C:15]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[C:31]4[NH:35][C:34](=[O:36])[O:33][N:32]=4)=[CH:21][CH:20]=3)=[C:14]([CH2:37][CH2:38][CH3:39])[N:13]=[C:12]2[CH3:40])=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 3-(4-isopropoxyphenyl)-2-methyl-5-{[2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-6-propylpyrimidin-4(3H)-one (200 g), ethanol (200 mL), and diisopropyl ether (400 mL) was added potassium 2-ethyl hexanoate and the mixture was stirred at 60° C. for 1 hr. To the mixture was added diisopropyl ether (1000 mL) dropwise. The mixture was stirred at reflux temperature for 24 hr, followed by being cooled to room temperature. The obtained precipitate was collected, washed with diisopropyl ether, and dried under reduced pressure at 60° C. for 1 hr to give the title compound (120 g, 56%) as colorless crystals.

Workup

stirringThe mixture was stirred
temperatureat reflux temperature for 24 hr
temperatureby being cooled to room temperature
customThe obtained precipitate was collected
washwashed with diisopropyl ether
customdried under reduced pressure at 60° C. for 1 hr

Sources & evidence

ORD record: ord-ec2f6da642854e5fab3d3e441398c084
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998968B2

Reaction notes

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