Phenylboronic Acid → 5-Phenylpyrimidine-2-carboxylic acid

HRID 1723828Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])O.[Na+]>COCCOC.C(=O)([O-])[O-].[Na+].[Na+].O.[Pd]>[C:11]1([C:2]2[CH:3]=[N:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 5-bromopyrimidine-2-carboxylic acid (5.01 g) and phenylboronic acid (3.61 g) in ethylene glycol dimethyl ether (150 ml), 2M aqueous sodium carbonate solution (100 ml) and tetralcistriphenylphosphine palladium (1.42 g) were added and stirred for 5 hours at 80° C. To the reaction liquid aqueous sodium hydrogencarbonate solution was added, diluted with water and washed with diethyl ether. To the aqueous layer 10% aqueous phosphoric acid was added to drop pH of the system to 4, followed by extraction with ethyl acetate, washing with saturated saline, drying over anhydrous sodium sulfate and concentration under reduced pressure. Thus the title compound (3.66 g) was obtained as white crystals. ESI-MS Found:m/z 201[M+H]+ ESI-MS Found:m/z 199[M−H]−

Workup

additionwas added
washwashed with diethyl ether
additionTo the aqueous layer 10% aqueous phosphoric acid was added
extractionfollowed by extraction with ethyl acetate
washwashing with saturated saline
dry with materialdrying over anhydrous sodium sulfate and concentration under reduced pressure

Sources & evidence

ORD record: ord-4b7c4a735a5041e78fa0ed665f5ca4cf
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07485647B2

Reaction notes

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