Water → 5-iodo-4-methyl-7-triisopropylsilanyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 509931Notes

Reaction equation

HRID 509931 reaction equation
[I:1][C:2]1[C:10]2[C:9]([CH3:11])=[N:8][CH:7]=[N:6][C:5]=2[NH:4][CH:3]=1.[H-].[Na+].[CH:14]([Si:17](Cl)([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])([CH3:16])[CH3:15].O>O1CCCC1>[I:1][C:2]1[C:10]2[C:9]([CH3:11])=[N:8][CH:7]=[N:6][C:5]=2[N:4]([Si:17]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[CH:14]([CH3:16])[CH3:15])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 139400Triisopropylsilyl chlorideHCID 582592995-iodo-4-methyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 582589665-iodo-4-methyl-7-triisopropylsilanyl-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 5-iodo-4-methyl-7H-pyrrolo[2,3-d]pyrimidine (19, 323.6 mg, 1.25 mmol) in 8 mL of tetrahydrofuran under nitrogen, sodium hydride (57.41 mg, 60% in mineral oil, 1.44 mmol) was added. The reaction was stirred at room temperature for 10 minutes, then triisopropysilyl chloride (3, 0.304 mL, 1.44 mmol) was added. The reaction was stirred at room temperature for 2 hours, then poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum to provide the desired compound.

Workup

  1. stirringThe reaction was stirred at room temperature for 2 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-898767a6d296432ba01713f3e587d277
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

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