Potassium Carbonate → HCID 86690335, compound

HRID 1428685Notes

Reaction equation

HRID 1428685 reaction equation
Br[C:2]1[C:3]([NH2:22])=[N:4][C:5]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[N:7]=1.[CH3:23][CH2:24][C:25]#[C:26][CH2:27][CH3:28].[Cl-].[Li+].[C:31]([O-:34])([O-])=[O:32].[K+].[K+]>CN(C=O)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:24]([C:25]1[N:22]([CH2:16][CH2:15][CH2:5][CH2:6][CH2:8][CH2:9][C:31]([OH:34])=[O:32])[C:3]2=[N:4][C:5]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=3)[N:7]=[C:2]2[C:26]=1[CH2:27][CH3:28])[CH3:23]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 13568Hex-3-yneHCID 433294Lithium ChlorideHCID 86690308HCID 86690308, compound

Product 1

HCID 86690335HCID 86690335, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 3-bromo-5,6-di-p-tolylpyrazin-2-amine (Ex 1, step 3) (20 mg, 0.056 mmol) in DMF (1 ml) bubbled with nitrogen was treated with hex-3-yne (0.013 ml, 0.113 mmol), palladium acetate (0.634 mg, 2.82 μmol), lithium chloride (2.393 mg, 0.056 mmol) and K2CO3 (39.0 mg, 0.282 mmol). The resulting mixture was heated at 120° C. for 30 min using microwave radiation. In parallel, a separate identical reaction mixture was prepared and heated thermally at 120° C. for 1 hour. After cooling to RT, the two reaction mixtures were combined in water (50 ml). The aqueous was extracted with EtOAc (×3). The combined organic extracts were washed sequentially with water (×1) and brine (×1), dried (MgSO4), filtered and concentrated under reduced pressure. Purification of the crude product by chromatography on silica eluting with 0-10% EtOAc in iso-hexane afforded the title compound;

Workup

  1. customIn parallel, a separate identical reaction mixture was prepared
  2. temperatureheated thermally at 120° C. for 1 hour
  3. temperatureAfter cooling to RT
  4. customthe two reaction mixtures
  5. extractionThe aqueous was extracted with EtOAc (×3)
  6. washThe combined organic extracts were washed sequentially with water (×1) and brine (×1)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customPurification of the crude product by chromatography on silica eluting with 0-10% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-4de5e41b8d9f47f7aaa927bbb8a6fea5
Source dataset
uspto-grants-2015_01
Patent number
US08937069B2

Reaction notes

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