Stannane, tributyl(1-ethoxyethenyl)- → 4-(1-Ethoxy-vinyl)-7-(toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 400559Notes

Reaction equation

HRID 400559 reaction equation
I[C:2]1[C:3]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:4]=2[N:5]=[CH:6][N:7]=1.C([Sn](CCCC)(CCCC)[C:26]([O:28][CH2:29][CH3:30])=[CH2:27])CCC>C1(C)C=CC=CC=1>[CH2:29]([O:28][C:26]([C:2]1[C:3]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:4]=2[N:5]=[CH:6][N:7]=1)=[CH2:27])[CH3:30]

Participants

4

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 586917404-iodo-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 586917324-(1-Ethoxy-vinyl)-7-(toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidineYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
90 °C

Procedure

[10 g, 25 mmol] of 4-Iodo-7-(toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidine was dissolved/suspended in 200 mL of dry toluene along with [2.0 g, 2.85 mmol] of palladium (II) bis-triphenylphosphine dichloride. The mixture was purged with nitrogen gas for ˜5 minutes before mixture was heated to 90° C. in an oil bath under an atmosphere of nitrogen gas. Added slowly dropwise over 2 hours, was [12.66 mL, 13.54 g, 37.5 mmol] of tri-n-butyl(1-ethoxyvinyl) tin in 100 mL of dry toluene. After completing the addition, the mixture was heated for an additional 6 hours under nitrogen. The reaction was cooled to ambient temperature and the solvent was removed under reduced pressure until the remaining volume was ⅕ the original. Added to this slurry was 160 mL of petroleum ether and the mixture was stirred for 1 hour, the solid being isolated via suction filtration and washed with petroleum ether. The damp solid was slurried in acetonitrile, stirred for one hour and the solid re-isolated via suction filtration and airdried. The resulting pale yellow solid, 7.2 g representing an 82% yield was utilized without further treatment.

Workup

  1. customThe mixture was purged with nitrogen gas for ˜5 minutes before mixture
  2. additionAdded slowly dropwise over 2 hours
  3. additionthe addition
  4. temperaturethe mixture was heated for an additional 6 hours under nitrogen
  5. temperatureThe reaction was cooled to ambient temperature
  6. customthe solvent was removed under reduced pressure until the remaining volume
  7. additionAdded to this slurry
  8. customthe solid being isolated via suction filtration
  9. washwashed with petroleum ether
  10. stirringstirred for one hour
  11. customthe solid re-isolated via suction filtration

Sources & evidence

ORD record
ord-e99c980c04234557a1bf3e87425ff43b
Source dataset
uspto-grants-2014_06
Patent number
US08741912B2

Reaction notes

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