Water → HCID 68580627, compound
Reaction equation
O[C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[C:4]([C:11]([F:14])([F:13])[F:12])[N:3]=1.[C:15](=[O:18])([O-])[O-].[K+].[K+].I[CH2:22][CH3:23].[OH2:24].[CH3:25]N(C)C=O>>[CH2:22]([O:24][C:8]([C:7]1[C:6]([O:18][CH2:15][CH3:25])=[N:5][C:4]([C:11]([F:14])([F:13])[F:12])=[N:3][CH:2]=1)=[O:10])[CH3:23]Participants
Procedure
4-Hydroxy-2-trifluoromethyl-pyrimidine-5-carboxylic acid (1 g, 4.828 mmol, Oakwood Products) was dissolved in dimethylformamide (10 mL) and potassium carbonate (1.668 g, 12.070 mmol) was added. After stirring at room temperature for 15 min, iodoethane (0.966 mL, 12.070 mmol) was added and the reaction mixture was stirred at room temperature for 3 d. Water was added, and the product was extracted with ethyl acetate (2×). The organic layers were washed with water (1×), brine (1×) and dried over anhydrous sodium sulfate. The solids were filtered off, and the filtrate was concentrated in vacuo. Purification of the residue by flash column chromatography (silica gel, eluting with a gradient of 5-50% ethyl acetate in hexanes) to give 4-ethoxy-2-trifluoromethyl-pyrimidine-5-carboxylic acid ethyl ester (852 mg, 67%).
Workup
- stirringthe reaction mixture was stirred at room temperature for 3 d
- extractionthe product was extracted with ethyl acetate (2×)
- washThe organic layers were washed with water (1×), brine (1×)
- dry with materialdried over anhydrous sodium sulfate
- filtrationThe solids were filtered off
- concentrationthe filtrate was concentrated in vacuo
- customPurification of the residue by flash column chromatography (silica gel
- washeluting with a gradient of 5-50% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-5a5bbfc537a54bc5adf2710876657224
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07705007B2
Reaction notes
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