Potassium Carbonate → HCID 24902229, compound
Reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:9]=[C:10](B(O)O)[CH:11]=[CH:12][C:13]=1[Cl:14].[Cl:18][C:19]1[CH:24]=[C:23](Cl)[N:22]=[CH:21][N:20]=1>O1CCOCC1>[Cl:18][C:19]1[CH:24]=[C:23]([C:10]2[CH:11]=[CH:12][C:13]([Cl:14])=[C:8]([Cl:7])[CH:9]=2)[N:22]=[CH:21][N:20]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
Potassium carbonate (2M solution, 200 ml, 400.0 mmol) was added in one portion to a stirred solution of 3,4-dichlorophenyl boronic acid (38.5 g, 201.4 mmol) and 4,6-dichloropyrimidine (50.0 g, 335.6 mmol) in dioxane (600 ml). The mixture was degassed with nitrogen for 5 minutes, after which time palladium tetrakis triphenylphosphine (7.78 g, 6.71 mmol) was added in one portion, the mixture was then heated to 90° C. and stirred at this temperature for 16 hours under a nitrogen atmosphere. After this time the reaction mixture was cooled to room temperature and concentrated. The resulting residue was dissolved in DCM (500 ml), washed sequentially with water (200 ml) then brine (200 ml) before being dried (MgSO4), filtered and concentrated to give the title compound (47.8 g, 91% yield) as a white solid which was used without further purification. Tr=2.32 min m/z (ES+) (M+H+) 258, 260.
Workup
- customThe mixture was degassed with nitrogen for 5 minutes
- temperatureAfter this time the reaction mixture was cooled to room temperature
- concentrationconcentrated
- dissolutionThe resulting residue was dissolved in DCM (500 ml)
- washwashed sequentially with water (200 ml)
- dry with materialbrine (200 ml) before being dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-fa6dcb42d2004109ac45d8698a34a05e
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09260422B2
Reaction notes
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