2-Bromopyrimidine → HCID 68180982, compound

HRID 538678Notes

Reaction equation

HRID 538678 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][NH:16][CH:17]1[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:27]1[N:32]=[CH:31][CH:30]=[CH:29][N:28]=1.CC([O-])(C)C.[Na+]>C1(C)C=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]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][N:16]([CH:17]1[CH2:18][C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:25]1)[C:27]1[N:32]=[CH:31][CH:30]=[CH:29][N:28]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 783452-BromopyrimidineHCID 23676156Sodium t-butoxideHCID 68181277HCID 68181277, compound

Product 1

HCID 68180982HCID 68180982, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

To a stirred solution of compound 44 (1.2 g, 3.48 mmol) in dry toluene (35 mL) were added 2-bromo-pyrimidine (0.55 g, 3.48 mmol) and NaOtBu (0.47 g, 4.88 mmol) and the solution was purged with argon for 30 minutes. Pd2(dba)3 (0.159 g, 0.17 mmol) and Verkade's super base (0.24 g, 0.70 mmol) were then added and the solution refluxed overnight. The reaction mixture was filtered through Celite®reagent and washed with ethyl acetate. The filtrate was washed with water and brine solution, dried over anhydrous Na2SO4, filtered and concentrated. The crude material was purified by Combiflash® chromatography eluting with 14-15% ethyl acetate-hexane to get compound 47.

Workup

  1. customthe solution was purged with argon for 30 minutes
  2. temperaturethe solution refluxed overnight
  3. filtrationThe reaction mixture was filtered through Celite®reagent
  4. washwashed with ethyl acetate
  5. washThe filtrate was washed with water and brine solution
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material was purified by Combiflash® chromatography
  10. washeluting with 14-15% ethyl acetate-hexane

Sources & evidence

ORD record
ord-ebc76de1fb3e49eab714ba7092232c10
Source dataset
uspto-grants-2014_10
Patent number
US08865741B2

Reaction notes

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