Potassium Carbonate → methyl 2-chloro-6-methoxypyrimidine-4-carboxylate
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4](Cl)[N:3]=1.[C:13]([O-])([O-])=[O:14].[K+].[K+]>CO>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4]([O:14][CH3:13])[N:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
A 30 mL round-bottomed vial was charged with methyl 2,6-dichloropyrimidine-4-carboxylate (0.6 g, 2.9 mmol, 1 equiv.), methanol (6 mL, 0.97 M), K2CO3 (0.401 g, 2.9 mmol, 1 equiv.), and the reaction mixture was shaken at 65° C. for 1.5 h. The solvent was concentrated under reduced pressure and the residue was partitioned between EtOAc (25 mL) and H2O (25 mL) and the water layer was extracted with EtOAc (2×20 mL). The combined organic layer was dried over Na2SO4 and concentrated under reduced pressure to provide the crude chloropyrimidine (441 mg, 588 mg theoretical, 75%), which was used in the next step without further purification.
Workup
- concentrationThe solvent was concentrated under reduced pressure
- customthe residue was partitioned between EtOAc (25 mL) and H2O (25 mL)
- extractionthe water layer was extracted with EtOAc (2×20 mL)
- dry with materialThe combined organic layer was dried over Na2SO4
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-bf9b73e01013424aa047220c2404f855
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08563539B2
Reaction notes
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