Sodium Carbonate → 4-(Pyrimidin-2-yl)benzoic acid
Reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1)([OH:3])=[O:2].Br[C:14]1[N:19]=[CH:18][CH:17]=[CH:16][N:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[N:15]1[CH:16]=[CH:17][CH:18]=[N:19][C:14]=1[C:7]1[CH:8]=[CH:9][C:4]([C:1]([OH:3])=[O:2])=[CH:5][CH:6]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a suspension of 4-carboxybenzeneboronic acid (0.660 g, 3.98 mmol) and 2-bromopyrimidine (0.630 g, 3.98 mmol) in dry acetonitrile (20 mL) was added 0.4 M aqueous sodium carbonate (20 mL) and the mixture was purged with nitrogen for 10 minutes. Tetrakis(triphenylphosphine)palladium(0) (240 mg) was then added and the reaction mixture heated to 90° C. for 17 hours. The hot reaction mixture was filtered through celite and concentrated in vacuo to remove the acetonitrile. The resulting aqueous suspension was washed with dichloromethane (2×30 mL) and then acidified to pH 1 by the addition of concentrated hydrochloric acid. The resulting white suspension was diluted with water (20 mL), filtered and the solid product dried in vacuo at 50° C. overnight to give the title compound (0.709 g, 89%) as a white solid, m.p. 237° C.
Workup
- customthe mixture was purged with nitrogen for 10 minutes
- additionTetrakis(triphenylphosphine)palladium(0) (240 mg) was then added
- filtrationThe hot reaction mixture was filtered through celite and
- concentrationconcentrated in vacuo
- customto remove the acetonitrile
- washThe resulting aqueous suspension was washed with dichloromethane (2×30 mL)
- additionacidified to pH 1 by the addition of concentrated hydrochloric acid
- additionThe resulting white suspension was diluted with water (20 mL)
- filtrationfiltered
- customthe solid product dried in vacuo at 50° C. overnight
Sources & evidence
- ORD record
- ord-89f2504517e24b3ca5f6b3e54bf8505b
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07678787B2
Reaction notes
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