Cesium carbonate → 3-Bromo-5-phenylpyrazin-2-amine
Reaction equation
[Br:1][C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6](Br)[N:7]=1.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C(O)C.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:9][C:3]1[C:2]([Br:1])=[N:7][C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][N:4]=1Participants
8
Reactant 3
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 75 °C
Procedure
To a stirred solution of 3,5-dibromo-2-aminopyrazine (200 mg; 0.79 mmol) and phenyl boronic acid (106 mg; 0.87 mmol) in dioxane (4 mL) and ethanol (2 mL) was added cesium carbonate (571 mg; 1.75 mmol in 2 mL of water) followed by Pd(PPh3)4 (46 mg; 0.04 mmol). The reaction was heated to 75° C. and stirred for 12 hours. The reaction was cooled to room temperature, diluted with 50 mL of ethyl acetate and washed with aqueous 10% sodium carbonate (1×50 mL), brine (50 mL), then dried (MgSO4) and filtered. The material was purified using a biotage 12L cartridge eluting with hexanes and ethyl acetate (3:1) to yield an off white solid (88% yield).
Workup
- temperatureThe reaction was cooled to room temperature
- washwashed with aqueous 10% sodium carbonate (1×50 mL), brine (50 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered
- customThe material was purified
- washeluting with hexanes and ethyl acetate (3:1)
Sources & evidence
- ORD record
- ord-2257fbe3e7c044d6a71b39ab6afa7136
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07608618B2
Reaction notes
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