Cesium carbonate → 6-Pyridin-3-yl-5-pyridin-4-yl-N-1,3-thiazol-2-ylpyrazin-2-amine

HRID 1710709Notes

Reaction equation

HRID 1710709 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:12]=[C:11]([NH2:13])[CH:10]=[N:9][C:8]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH:2]=1.Br[C:21]1[S:22][CH:23]=[CH:24][N:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:12]=[C:11]([NH:13][C:21]3[S:22][CH:23]=[CH:24][N:25]=3)[CH:10]=[N:9][C:8]=2[C:14]2[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=2)[CH:2]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 764302-BromothiazoleHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 16071665HCID 16071665, compound

Product 1

HCID 594575686-Pyridin-3-yl-5-pyridin-4-yl-N-1,3-thiazol-2-ylpyrazin-2-amineYield 44%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

An oven dried resealable Schlenk tube was charged with 6-pyridin-3-yl-5-pyridin-4-ylpyrazin-2-amine (Example 13, 60 mg, 0.241 mmol), 2-bromo-1,3-thiazole (22 μL, 0.241 mmol), cesium carbonate (110 mg, 0.337 mmol) and dioxane (2.5 mL). The Schlenk tube was subjected to three cycles of evacuation-backfilling with argon, and tris(dibenzylideneacetone)dipalladium(0) (9 mg, 0.01 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (11 mg, 0.019 mmol) was added. After three new cycles of evacuation-backfilling with argon, the Schlenk tube was capped and placed in a 100° C. oil bath. After 16 h, the mixture was cooled, partitioned between water and ethyl acetate, the aqueous phase was extracted twice with ethyl acetate, the organic layers washed with brine, dried (MgSO4) and evaporated. Flash chromatography (95:5 dichloromethane/methanol) furnished the title compound as a solid (35 mg, 44%).

Workup

  1. customAn oven dried resealable Schlenk tube
  2. additionwas added
  3. customAfter three new cycles of evacuation-backfilling with argon, the Schlenk tube was capped
  4. customplaced in a 100° C.
  5. temperaturethe mixture was cooled
  6. custompartitioned between water and ethyl acetate
  7. extractionthe aqueous phase was extracted twice with ethyl acetate
  8. washthe organic layers washed with brine
  9. dry with materialdried (MgSO4)
  10. customevaporated

Sources & evidence

ORD record
ord-1d219bb66e734daaaa4422d076d7db08
Source dataset
uspto-grants-2010_09
Patent number
US07790728B2

Reaction notes

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