Chlorosuccinimide → HCID 135829595, compound
Reaction equation
[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[NH:14][CH:13]=[N:12][C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:18]N1C(=O)CCC1=O>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[NH:14][CH:13]=[N:12][C:11]=2[N:10]=[C:9]1[Cl:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
12.748 g of 7-benzyl-1,7-dihydropurin-6-one was dissolved in 150 ml of N,N-dimethylformamide, and 7.9 g of N-chlorosuccinimide was added thereto. The reaction solution was stirred overnight, and then diluted with ethyl acetate. The solution was washed with water and 1N hydrochloric acid, and dried over anhydrous magnesium sulfate. The solution was filtered, and the filtrate was concentrated to give 6.103 g of 7-benzyl-8-chloro-1,7-dihydropurin-6-one. This compound was combined with 20 g of t-butyl piperazine-1-carboxylate, and the mixture was heated at 150° C. After being stirred for one hour, the reaction mixture was combined with ethyl acetate and water, and partitioned. The organic layer was washed with 1N hydrochloric acid, and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated. The residue was purified by silica gel column chromatography. Thus, 1.539 g of the title compound was obtained from the fraction eluted with ethyl acetate-methanol (10:1).
Workup
- washThe solution was washed with water and 1N hydrochloric acid
- dry with materialdried over anhydrous magnesium sulfate
- filtrationThe solution was filtered
- concentrationthe filtrate was concentrated
Sources & evidence
- ORD record
- ord-005db6546de541bb97f1781fac9d4293
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07772226B2
Reaction notes
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