1,8-Diazabicyclo(5.4.0)undec-7-ene → 7-Allyl-8-(3,5-dimethylpiperazin-1-yl)-1,3-dimethyl-3,7-dihydropurine-2,6-dione

HRID 1792001Notes

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].[CH3:18][C@H:19]1[CH2:24][NH:23][CH2:22][C@@H:21]([CH3:25])[NH:20]1.N12CCCN=C1CCCCC2>CN1CCCC1=O.C(OCC)(=O)C.O>[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]1[N:23]1[CH2:22][CH:21]([CH3:25])[NH:20][CH:19]([CH3:18])[CH2:24]1)[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 150 °C

Procedure

A suspension of 7-allyl-8-chloro-1,3-dimethyl-3,7-dihydropurine-2,6-dione (200 mg), cis-2,6-dimethylpiperazine (107 mg), and 1,8-diazabicyclo[5.4.0]undec-7-ene (128 μl) in 1-methyl-2-pyrrolidone (2 ml) was stirred at 150° C. for 50 minutes. The reaction mixture was diluted with ethyl acetate and water, and extracted with ethyl acetate. The aqueous layer was extracted with chloroform, and the combined organic layer was washed with water and dried over magnesium sulfate. The solvent was removed by distillation at reduced pressure to give brown oil. The oil was purified by silica gel column chromatography, and 111 mg of the title compound was obtained from a fraction eluted with methanol-ethyl acetate (1:10).

Workup

extractionextracted with ethyl acetate
extractionThe aqueous layer was extracted with chloroform
washthe combined organic layer was washed with water
dry with materialdried over magnesium sulfate
customThe solvent was removed by distillation at reduced pressure
customto give brown oil
customThe oil was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-fa8fc4c9e9274884abd572fa6fada0e9
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074798B2

Reaction notes

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