Potassium Phosphate, Tribasic → 2-Chloro-5-cyclopropylpyrimidine
Reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH:9]1(B(O)O)[CH2:11][CH2:10]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:8][C:5]1[N:4]=[CH:3][C:2]([CH:9]2[CH2:11][CH2:10]2)=[CH:7][N:6]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 120 °C
Procedure
A mixture of 5-bromo-2-chloropyrimidine (100 mg, 0.517 mmol, Aldrich), cyclopropylboronic acid (57.7 mg, 0.672 mmol, Aldrich), Tricyclohexylphosphine (14.50 mg, 0.052 mmol, Aldrich) and K3PO4 (384 mg, 1.81 mmol, EMD) in Toluene (2 mL) and Water (0.110 mL) was degassed by vacuum and purged with Ar. To the resulting mixture was added Palladium(II) acetate (5.80 mg, 0.026 mmol, Stem) and then heated under microwave conditions at 120° C. for 10 min. The reaction mixture was quenched with H2O and then extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to a yellow oil. The oil was purified by flash chromatography (SiO2, 0 to 20% EtOAc in Hexanes) to yield 71 mg of the desired compound as a white solid. MS (ESI) 155 (M+H).
Workup
- customwas degassed by vacuum
- custompurged with Ar
- customThe reaction mixture was quenched with H2O
- extractionextracted with EtOAc (2×)
- washThe combined organic layers were washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo to a yellow oil
- customThe oil was purified by flash chromatography (SiO2, 0 to 20% EtOAc in Hexanes)
Sources & evidence
- ORD record
- ord-d2c4fe79d2ee497e95be240b46938803
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08513424B2
Reaction notes
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