2-(Tributylstannyl)-1,3-thiazole → 2-[6-(1,3-Thiazol-2-yl)pyridin-2-yl]pyrimidine

HRID 705038Notes

Reaction equation

HRID 705038 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[S:7][CH:8]=[CH:9][N:10]=1)CCC.Br[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]2[N:31]=[CH:30][CH:29]=[CH:28][N:27]=2)[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:7]1[CH:8]=[CH:9][N:10]=[C:6]1[C:20]1[N:21]=[C:22]([C:26]2[N:27]=[CH:28][CH:29]=[CH:30][N:31]=2)[CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 158812582-(6-Bromopyridin-2-yl)pyrimidine

Product 1

HCID 675166562-[6-(1,3-Thiazol-2-yl)pyridin-2-yl]pyrimidine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Under argon, 2.69 g (7.18 mmol) of 2-tributylstannylthiazole, 1.69 g (7.18 mmol) of 2-bromo-6-pyrimidylpyridine and 0.49 g (0.43 mmol) of tetrakis(triphenylphosphine)palladium were stirred in 100 ml of toluene at 100° C. for 16 hours. For work-up, the solvent was removed under reduced pressure, the crude product was dissolved in dichloromethane and stirred with saturated potassium fluoride solution for 16 hours, the mixture was filtered through Celite and the organic phase was concentrated. Further purification by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate). This gave 0.93 g (54% of theory) of 2-[6-(1,3-thiazol-2-yl)pyridin-2-yl]pyrimidine which was used for subsequent reactions.

Workup

  1. customFor work-up, the solvent was removed under reduced pressure
  2. dissolutionthe crude product was dissolved in dichloromethane
  3. filtrationthe mixture was filtered through Celite
  4. concentrationthe organic phase was concentrated
  5. customFurther purification by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-1924ef0096434490b7e98eee02a45b28
Source dataset
uspto-grants-2015_11
Patent number
US09173396B2

Reaction notes

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