2-(Tributylstannyl)pyrimidine → HCID 59007792, compound

HRID 641088Notes

Reaction equation

HRID 641088 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:10]([Cl:17])=[N:11][C:12](Cl)=[CH:13][C:14]=1[Cl:15].C([Sn](CCCC)(CCCC)[C:23]1[N:28]=[CH:27][CH:26]=[CH:25][N:24]=1)CCC>CN(C)C=O.O1CCOCC1.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>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:10]([Cl:17])=[N:11][C:12]([C:23]2[N:28]=[CH:27][CH:26]=[CH:25][N:24]=2)=[CH:13][C:14]=1[Cl:15]

Participants

6

Reactant 2

HCID 27632512-(Tributylstannyl)pyrimidineHCID 57430841HCID 57430841, compound

Product 1

HCID 59007792HCID 59007792, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

14.6 g (0.047 mol) of 3-(2-chloro-6-fluorophenyl)-2,4,6-trichloropyridine (see Example Ab), 20.0 g (0.051 mol) of 2-tri-n-butylstannylpyrimidine and 1.1 g (0.94 mmol) of tetrakistriphenylphosphinepalladium(0), dissolved in 70 ml of dimethylformamide and 50 ml of 1,4-dioxane, were kept at 110° C. for 10 h. After removal of the volatile components under reduced pressure, the product was purified on silica gel using cyclohexane/ethyl acetate. Yield 2.0 g of yellow crystals (m.p. 147° C.).

Workup

  1. customAfter removal of the volatile components under reduced pressure
  2. customthe product was purified on silica gel

Sources & evidence

ORD record
ord-393b0b96700b42c791c5774f86112790
Source dataset
uspto-grants-2010_04
Patent number
US07695728B2

Reaction notes

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