Water → 1-(3-chloropropyl)-5-phenyl-2,4(1H,3H)-pyrimidinedione
Reaction equation
[C:1]1([C:7]2[C:8](=[O:14])[NH:9][C:10](=[O:13])[NH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:22][CH2:23][CH2:24][Cl:25].O>CN(C=O)C>[Cl:25][CH2:24][CH2:23][CH2:22][N:11]1[CH:12]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8](=[O:14])[NH:9][C:10]1=[O:13]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 5-phenyl-2,4(1H,3H)-pyrimidinedione (527 mg, commercially available from Akos) and K2CO3 (386 mg) in dry DMF (10 mL) was stirred for 1 hour at room temperature. 1-Bromo-3-chloropropane (0.28 mL) was added and the mixture was stirred at room temperature for 20 hours. One more portion of 1-bromo-3-chloropropane (0.14 mL) was added and the mixture was stirred at room temperature for 20 hours. Water was added and the resulting mixture was extracted with ethyl acetate. The organic phases were washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by a silica flash chromatography (eluting with A: dichloromethane, B: dichloromethane/methanol=9/1 at ratio A:B=6:4) to give the title compound as a colourless oil (150 mg).
Workup
- stirringthe mixture was stirred at room temperature for 20 hours
- extractionthe resulting mixture was extracted with ethyl acetate
- washThe organic phases were washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
- customThe crude product was purified by a silica flash chromatography (
- washeluting with A: dichloromethane, B
Sources & evidence
- ORD record
- ord-8a8197255c98431ca6db0b3bf5cce1ee
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07727988B2
Reaction notes
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