4,6-Dichloropyrimidine → HCID 22251374, compound

HRID 1175555Notes

Reaction equation

HRID 1175555 reaction equation
C([Sn]([C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)(CCCC)CCCC)CCC.Cl[C:20]1[CH:25]=[C:24](Cl)[N:23]=[CH:22][N:21]=1>C1(C)C=CC=CC=1.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>[S:15]1[CH:16]=[CH:17][CH:18]=[C:14]1[C:20]1[CH:25]=[C:24]([C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)[N:23]=[CH:22][N:21]=1

Participants

5

Reactant 2

HCID 709434,6-DichloropyrimidineHCID 27793732-(Tri-n-butylstannyl)thiophene

Product 1

HCID 22251374HCID 22251374, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of tri-n-butylstannylthiophene (10.52 g, 28.19 mmol), 4,6-dichloropyrimidine (2.00 g, 13.42 mmol), tetrakis(triphenylphosphine)palladium(0) (0.345 g, 0.30 mmol) and few crystals of 2,6-di-tert-butyl-4-methylphenolo in dry toluene (20 mL) was deareated twice with nitrogen. The reaction mixture was refluxed for 6 hours and, after cooling, a white precipitate was formed in the reaction flask. The solid was collected and the organic phase was diluted with ether (100 mL), poured onto a solution of NH4F (3 g, 100 ml) and separated. After drying over MgSO4, the solvent was evaporated affording a solid material. The two solid phase were combined and crystallized from toluene to give the pure product as a white crystals (2.36 g, 9.66 mmol, 72.0% yield). mp 146° C.; 1H NMR (CDCl3) δ 9.07 (1H, d, 2J=1.4), 7.86 (1H, d, 2J=3.7), 7.83 (1H, d), 7.57 (1H, d, 2J=5.1), 7.20 (1H, dd).

Workup

  1. temperatureThe reaction mixture was refluxed for 6 hours
  2. temperatureafter cooling
  3. customa white precipitate was formed in the reaction flask
  4. customThe solid was collected
  5. additionthe organic phase was diluted with ether (100 mL)
  6. additionpoured onto a solution of NH4F (3 g, 100 ml)
  7. customseparated
  8. dry with materialAfter drying over MgSO4
  9. customthe solvent was evaporated
  10. customaffording a solid material
  11. customcrystallized from toluene

Sources & evidence

ORD record
ord-8ce5542a523d417f938e020c28400577
Source dataset
uspto-grants-2010_11
Patent number
US07842198B2

Reaction notes

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