Water → 5-bromo-6-(4'-cyclohexylbenzyloxy)-3-ethyl-2-methylthio-4(3H)-pyrimidinone
Reaction equation
[Br:1][C:2]1[C:3](=[O:13])[N:4]([CH2:11][CH3:12])[C:5]([S:9][CH3:10])=[N:6][C:7]=1[OH:8].[CH:14]1([C:20]2[CH:27]=[CH:26][C:23]([CH2:24]Cl)=[CH:22][CH:21]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:1][C:2]1[C:3](=[O:13])[N:4]([CH2:11][CH3:12])[C:5]([S:9][CH3:10])=[N:6][C:7]=1[O:8][CH2:24][C:23]1[CH:26]=[CH:27][C:20]([CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)=[CH:21][CH:22]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
In 20 ml of N,N-dimethylformamide were dissolved 1 g of 5-bromo-3-ethyl-6-hydroxy-2-methylthio-4(3H)-pyrimidinone and 0.8 g of 4-cyclohexylbenzyl chloride, and then 1 g of anhydrous potassium carbonate was added thereto. The mixture was subjected to a reaction at 80° C. for 3 hours. After allowing to cool in air, the resulting solution was poured into 50 ml of water and extracted twice with 30 ml of ethyl ether. The ethyl ether layer was washed with water, dried over anhydrous sodium sulfate and then freed of solvent by distillation under reduced pressure to give 1.65 g of a crude product.
Workup
- customThe mixture was subjected to a reaction at 80° C. for 3 hours
- temperatureto cool in air
- extractionextracted twice with 30 ml of ethyl ether
- washThe ethyl ether layer was washed with water
- dry with materialdried over anhydrous sodium sulfate
- distillationfreed of solvent by distillation under reduced pressure
Sources & evidence
- ORD record
- ord-327ddeef711c4e229ac43d89120d90bf
- Source dataset
- uspto-grants-1990_03
- Patent number
- US04908379
Reaction notes
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