Water → 1-(4-Chloro-butyl)-5-(2,4-dimethyl-oxazol-5-yl)-1H-pyrimidine-2,4-dione
Reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:8]2[C:9](=[O:15])[NH:10][C:11](=[O:14])[NH:12][CH:13]=2)=[C:5]([CH3:7])[N:6]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:23][CH2:24][CH2:25][CH2:26][Cl:27].O>CN(C=O)C>[Cl:27][CH2:26][CH2:25][CH2:24][CH2:23][N:12]1[CH:13]=[C:8]([C:4]2[O:3][C:2]([CH3:1])=[N:6][C:5]=2[CH3:7])[C:9](=[O:15])[NH:10][C:11]1=[O:14]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
5-(2,4-Dimethyl-oxazol-5-yl)-1H-pyrimidine-2,4-dione (Prep61, 300 mg, 1.45 mmol) was dissolved in dry DMF (4 ml) and K2CO3 (300 mg, 2.17 mmol) was added. The mixture was stirred at room temperature for 1 h, then a solution of 1-bromo-4-chloro-butane (commercially available from Aldrich, 496 mg, 2.9 mmol) in dry DMF (1 ml) was added. After stirring the reaction at room temperature for 48 hours, water was added and the mixture was extracted with diethylether. The aqueous layer was then extracted with ethyl acetate. The organic phase was dried (Na2SO4), filtered and evaporated; the crude was used without further purification in the next step (200 mg, 47% yield).
Workup
- stirringAfter stirring
- customthe reaction at room temperature for 48 hours
- extractionthe mixture was extracted with diethylether
- extractionThe aqueous layer was then extracted with ethyl acetate
- dry with materialThe organic phase was dried (Na2SO4)
- filtrationfiltered
- customevaporated
- customthe crude was used without further purification in the next step (200 mg, 47% yield)
Sources & evidence
- ORD record
- ord-d5dea396028e4bdbb87f348e3420a44f
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07727988B2
Reaction notes
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