Sodium Carbonate → HCID 20491752, compound
Reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[N:5][C:6](=[O:9])[NH:7][CH:8]=1.Cl[CH2:11][C:12]1[C:13]([CH3:18])=[N:14][O:15][C:16]=1[CH3:17].C(=O)([O-])[O-].[Na+].[Na+]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.CN(C)C=O.O>[Cl:2][C:3]1[CH:4]=[N:5][C:6](=[O:9])[N:7]([CH2:11][C:12]2[C:13]([CH3:18])=[N:14][O:15][C:16]=2[CH3:17])[CH:8]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 90 °C
Procedure
A mixture of 5-chloropyrimidin-2-one hydrochloride (0.668 g), 4-chloromethyl-3,5-dimethylisoxazole (0.874 g), anhydrous sodium carbonate (1.272 g) and benzyltrimethylammonium chloride (15 mg) in dimethylformamide (20 ml) was stirred and heated at 90° C. After 2.25 h the reaction mixture was diluted with water (200 ml) and extracted with ethyl acetate (100 ml, 2×50 ml). The combined extracts were washed with water (50 ml) and brine (50 ml), dried (MgSO4) and evaporated to an orange crystalline solid (0.811 g). The solid was subjected to preparative layer chromatography (p.l.c.) on silica developing with chloroform-ethyl acetate (1:1) (two runs). The major band was eluted with chloroform-ethanol (1:1) (three times) to give a cream crystalline solid (0.313 g) which was recrystallised from ethanol to give the title pyrimidone (0.189 g) m.p. 218°-219° C. (Kofler), λmax (EtOH) 225 nm (ε 9,300), 310 nm (ε 2,200) inflection at 245 nm (ε 4,300) νmax (CHBr3) 1677 cm-1 (C=O), (Nujol) 1668 cm-1 (C=O).
Workup
- extractionextracted with ethyl acetate (100 ml, 2×50 ml)
- washThe combined extracts were washed with water (50 ml) and brine (50 ml)
- dry with materialdried (MgSO4)
- customevaporated to an orange crystalline solid (0.811 g)
- washThe major band was eluted with chloroform-ethanol (1:1) (three times)
Sources & evidence
- ORD record
- ord-173a9656d0ca47809ff36414d4e0908e
- Source dataset
- uspto-grants-1983_08
- Patent number
- US04399140
Reaction notes
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