2-(Methylthio)-4-(tributylstannyl)pyrimidine → HCID 17962398, compound

HRID 1374726Notes

Reaction equation

HRID 1374726 reaction equation
Br[C:2]1[C:3]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)=[N:4][N:5]2[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:6]=12.[CH3:25][S:26][C:27]1[N:32]=[C:31]([Sn](CCCC)(CCCC)CCCC)[CH:30]=[CH:29][N:28]=1>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Ag-]=O>[F:14][C:11]([F:12])([F:13])[C:9]1[CH:8]=[CH:7][C:6]2[N:5]([N:4]=[C:3]([C:15]3[CH:16]=[CH:17][C:18]([C:21]([F:22])([F:24])[F:23])=[CH:19][CH:20]=3)[C:2]=2[C:31]2[CH:30]=[CH:29][N:28]=[C:27]([S:26][CH3:25])[N:32]=2)[CH:10]=1

Participants

6

Reactant 2

HCID 27632612-(Methylthio)-4-(tributylstannyl)pyrimidineHCID 17962402HCID 17962402, compound

Product 1

HCID 17962398HCID 17962398, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 178418778HCID 178418778, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-bromo-6-(trifluoromethyl)-2-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridine (0.82 g), 2-(methylthio)-4-(tributylstannyl)pyrimidine (0.83 g), dichlorobis(triphenylphosphine)palladium (0.14 g) and silver (I) oxide (0.43 g) in 1,4-dioxane (10 mL) was heated to reflux for 18 h. The mixture was cooled, filtered and the filtrate concentrated to dryness. The residue was purified by chromatography eluting with an increasing gradient from cyclohexane to cyclohexane-diethylether (94:6) to give, after concentration to dryness of the appropriate fractions, the title compound as a cream solid (0.46 g); 1H NMR (d6-DMSO) δ 9.58(1H, s), 8.50(1H, d), 8.46(1H, d), 7.90(2H, d), 7.84 (2H, d), 7.82(1H, dd), 6.94(1H, d), 2.43(3H, s); m/z 455 (M+1)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 h
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated to dryness
  6. customThe residue was purified by chromatography
  7. washeluting with an increasing gradient from cyclohexane to cyclohexane-diethylether (94:6)
  8. customto give
  9. concentrationafter concentration to dryness of the appropriate fractions

Sources & evidence

ORD record
ord-6674094db76d425b9e57549c65e3cd99
Source dataset
uspto-grants-2007_01
Patent number
US07166597B2

Reaction notes

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