Potassium Carbonate → tert-Butyl 5-[3-methyl-7-(3-methyl-but-2-enyl)-2,6-dioxo-1-(2-oxo-2-phenyl-ethyl)-2,3,6,7-tetrahydro-1H-purin-8-yl]-cis-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylate

HRID 1174574Notes

Reaction equation

Br[C:2]1[N:10]([CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[C:9]2[C:8](=[O:16])[N:7]([CH2:17][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:6](=[O:26])[N:5]([CH3:27])[C:4]=2[N:3]=1.[CH2:28]1[C@@H:32]2[CH2:33][NH:34][CH2:35][C@@H:31]2[CH2:30][N:29]1[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:27][N:5]1[C:4]2[N:3]=[C:2]([N:34]3[CH2:33][C@@H:32]4[CH2:28][N:29]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:30][C@@H:31]4[CH2:35]3)[N:10]([CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[C:9]=2[C:8](=[O:16])[N:7]([CH2:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:6]1=[O:26]

Participants

Conditions

Temperature: 90 °C

Procedure

52 mg of 8-bromo-3-methyl-7-(3-methyl-but-2-enyl)-1-(2-oxo-2-phenyl-ethyl)-3,7-dihydro-purine-2,6-dione were dissolved in 1 ml of DMF, and 56 mg of tert-butyl cis-hexahydropyrrolo[3,4-c]pyrrole-2-carboxylate and 36.5 mg of potassium carbonate were added. The mixture was stirred at 90° C. for 5 hours, cooled and evaporated in a vacuum. The oily residue was purified by column chromatography (silica gel: mobile phase: methylene chloride: methanol=98:2).

Workup

temperaturecooled
customevaporated in a vacuum
customThe oily residue was purified by column chromatography (silica gel: mobile phase: methylene chloride: methanol=98:2)

Sources & evidence

ORD record: ord-6e98d4e3531e4d559838181eacd17f53
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07838528B2

Reaction notes

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