Dimethylformamide → Ethyl (7-benzyl-2,6-dioxo-1,2,6,7-tetrahydro-3H-purin-3-yl)acetate

HRID 1792071Notes

Reaction equation

[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[NH:14][C:13](=[O:18])[NH:12][C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.Br[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]>C(OCC)(=O)C.O>[CH2:35]([O:34][C:32](=[O:33])[CH2:31][N:12]1[C:11]2[N:10]=[CH:9][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:16]=2[C:15](=[O:17])[NH:14][C:13]1=[O:18])[CH3:36]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 7-benzyl-3,7-dihydropurine-2,6-dione (3.0 g), anhydrous potassium carbonate (2.0 g), and N,N-dimethylformamide (60 ml) was stirred with heating in an oil bath of 40° C., and ethyl bromoacetate (1.5 g) was added thereto. The mixture was stirred by heating at the same temperature for 4 hours. The reaction mixture was diluted with ethyl acetate and water, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using 20–40% (20% 2-propanol/ethyl acetate)/hexane to give 1.3 g of the title compound.

Workup

stirringThe mixture was stirred
temperatureby heating at the same temperature for 4 hours
extractionextracted with ethyl acetate
washThe organic layer was washed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-4b79b7d05e904ad699295bfc2c1e43f1
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074798B2

Reaction notes

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