1,3-Dimethyl-6-(piperazin-1-yl)pyrimidine-2,4(1H,3H)-dione → HCID 19011765, compound
Reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH2:13]CS([O-])(=O)=O)(=[O:4])=[O:3].[CH3:19][N:20]1[C:25]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:24][C:23](=[O:32])[N:22]([CH3:33])[C:21]1=[O:34]>C(Cl)(Cl)Cl>[CH3:19][N:20]1[C:25]([N:26]2[CH2:31][CH2:30][N:29]([CH2:13][CH2:12][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[O:5][S:2]([CH3:1])(=[O:3])=[O:4])[CH2:28][CH2:27]2)=[CH:24][C:23](=[O:32])[N:22]([CH3:33])[C:21]1=[O:34]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
A mixture of 1 g of 2-(2-methanesulfonyloxyphenyl)ethylmethane sulfonate and 0.65 g of 1,3-dimethyl-6-(piperazin-1-yl)-2,4(1H,3H)-pyrimidinedione was stirred at 90° C. for 2 hours and then allowed to stand for cooling. The resultant reaction mixture was dissolved in 50 ml of chloroform, and then washed with 10 ml of a 1N aqueous sodium hydroxide solution. The chloroform layer was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the residue was purified through a silica gel column chromatograph (chloroform/methanol=40/1 in volume ratio), thereby obtaining 2.0 g of 1,3-dimethyl-6-[4-(2-[2-methanesulfonyloxyphenyl]ethyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione.
Workup
- temperaturefor cooling
- customThe resultant reaction mixture
- washwashed with 10 ml of a 1N aqueous sodium hydroxide solution
- washThe chloroform layer was washed with water
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customthe residue was purified through a silica gel column chromatograph (chloroform/methanol=40/1 in volume ratio)
Sources & evidence
- ORD record
- ord-ba58be98ec844d3cb21ebd9aca9c1a98
- Source dataset
- uspto-grants-1994_07
- Patent number
- US05332739
Reaction notes
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