1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-(7-Allyl-1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)piperazine-1-carboxylic acid tert-butyl ester

HRID 1791999Notes

Reaction equation

[CH2:1]([N:4]1[C:12]2[C:11](=[O:13])[N:10]([CH3:14])[C:9](=[O:15])[N:8]([CH3:16])[C:7]=2[N:6]=[C:5]1Cl)[CH:2]=[CH2:3].[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].N12CCCN=C1CCCCC2>CN1CCCC1=O>[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][N:28]([C:5]2[N:4]([CH2:1][CH:2]=[CH2:3])[C:12]3[C:11](=[O:13])[N:10]([CH3:14])[C:9](=[O:15])[N:8]([CH3:16])[C:7]=3[N:6]=2)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 7-allyl-8-chloro-1,3-dimethyl-3,7-dihydropurine-2,6-dione (1.0 g), piperazine-1-carboxylic acid tert-butyl ester (1.1 g), 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU) (0.59 ml), and 1-methylpyrrolidin-2-one (2 ml) were stirred under nitrogen atmosphere in an oil bath at 140° C. for 2 hours. The reaction mixture was extracted with ethyl acetate and water. The organic layer was washed with water followed by saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with 10–20% (20% 2-propanol/ethyl acetate)/hexane to give 1.5 g of the title compound.

Workup

extractionThe reaction mixture was extracted with ethyl acetate and water
washThe organic layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography with 10–20% (20% 2-propanol/ethyl acetate)/hexane

Sources & evidence

ORD record: ord-c838971beba043dab0973b4dd0a71f71
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074798B2

Reaction notes

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