Sodium Carbonate → HCID 117819052, compound
Reaction equation
[OH:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]=1[CH3:13].[Na+].Cl[C:16]([F:21])([F:20])C([O-])=O.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[NH4+]>CN(C=O)C.C(#N)C>[F:20][CH:16]([F:21])[O:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]=1[CH3:13]Participants
Conditions
- Temperature
- 90 °C
Procedure
In a round bottom flask (5 litre) was taken Ethyl 6-hydroxy-5-methylpyrimidine-4-carboxylate 40 (85 g, 466 mmol), chlorodifluoroacetic acid sodium salt (106.7 g, 699 mmol), sodium carbonate (98.9 g, 933 mmol), acetonitrile (1500 ml) and DMF (425 ml). The reaction mixture was heated to 90° C. for 16 h. The Progress of the reaction was monitored by LCMS. The reaction mixture was cooled to room temperature and then neutralized with saturated ammonium chloride. The solvent was removed under vacuum and extracted with ethyl acetate. The combined organic layer was washed with water, brine and concentrated under reduced pressure. The crude compound was purified through silica gel chromatography eluting (3-4% ethyl acetate) to afford ethyl 6-(difluoromethoxy)-5-methylpyrimidine-4-carboxylate 48b as a pale yellow liquid. Yield: 14 g (13%).
Workup
- customIn a round bottom flask (5 litre) was taken
- temperatureThe reaction mixture was cooled to room temperature
- customThe solvent was removed under vacuum
- extractionextracted with ethyl acetate
- washThe combined organic layer was washed with water, brine
- concentrationconcentrated under reduced pressure
- customThe crude compound was purified through silica gel chromatography
- washeluting (3-4% ethyl acetate)
Sources & evidence
- ORD record
- ord-246e2201b73448b9bf8b9bdf0c601aad
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09163020B2
Reaction notes
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