Sodium Carbonate → 2-Fluoro-3-(4-fluorotetrahydro-2H-pyran-4-YL)pyrazine
Reaction equation
[F:1][C:2]1[C:3]([C:8]2(O)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1.CCN(S(F)(F)[F:21])CC.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[F:1][C:2]1[C:3]([C:8]2([F:21])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1Participants
5
Conditions
- Temperature
- 0 °C
Procedure
A solution of 4-(3-fluoropyrazin-2-yl)tetrahydro-2H-pyran-4-ol (0.4 g, 2.018 mmol) in CH2Cl2 (6.73 mL) was cooled to 0° C. DAST (0.533 mL, 4.04 mmol) was added to the reaction mixture dropwise and the resulting mixture was allowed to stir at 0° C. for 2 hr. A solution of saturated sodium carbonate was added dropwise to the reaction mixture at 0° C. to quench the reaction. The heterogeneous mixture was stirred vigorously for 1 hr to ensure complete quenching. Mixture was transferred to a separatory funnel and the layers were separated after addition of more DCM and saturated bicarbonate solution. The organic layer was dried over magnesium sulfate and rotovapped to remove the volatile solvent.
Workup
- customto quench
- customthe reaction
- stirringThe heterogeneous mixture was stirred vigorously for 1 hr
- customMixture was transferred to a separatory funnel
- customthe layers were separated
- additionafter addition of more DCM and saturated bicarbonate solution
- dry with materialThe organic layer was dried over magnesium sulfate
- customto remove the volatile solvent
Sources & evidence
- ORD record
- ord-4e0d765fe628466296a48e23e7efa12f
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08247418B2
Reaction notes
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