2,6-Lutidine → HCID 59289323, compound

HRID 2191055Notes

Reaction equation

HRID 2191055 reaction equation
[N:1]([C@@:4]1(/[CH:29]=[CH:30]/[P:31](=[O:38])([O:35]CC)[O:32]CC)[C@@H:8]([OH:9])[C@@H:7]([OH:10])[C@H:6]([N:11]2[CH:19]=[N:18][C:17]3[C:12]2=[N:13][CH:14]=[N:15][C:16]=3[NH:20][C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:5]1)=[N+:2]=[N-:3].N1C(C)=CC=CC=1C.[Si](I)(C)(C)C>CC#N>[N:1]([C@@:4]1(/[CH:29]=[CH:30]/[P:31](=[O:32])([OH:35])[OH:38])[C@@H:8]([OH:9])[C@@H:7]([OH:10])[C@H:6]([N:11]2[CH:19]=[N:18][C:17]3[C:12]2=[N:13][CH:14]=[N:15][C:16]=3[NH:20][C:21](=[O:28])[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[O:5]1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 85247Trimethylsilyl iodideHCID 86641127HCID 86641127, compound

Product 1

HCID 59289323HCID 59289323, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 36.5 (261 mg, 0.48 mmol) was dissovled in CH3CN (9.6 mL), treated with 2,6-lutidine (0.55 mL, 4.2 mmol) and TMSI (0.34 mL, 2.39 mmol). The mixture was stirred at r.t. for 30 min and concentrated under reduced pressure. Saturated NaHCO3 was added to the residue and the mixture was stirred for 5 min. The solvent was then removed under redued pressure and CH3CN was added, the mixture was filtered and concentrated under reduced pressure. The residue was used for the next step reaction without further purification.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionSaturated NaHCO3 was added to the residue
  3. stirringthe mixture was stirred for 5 min
  4. customThe solvent was then removed under redued pressure and CH3CN
  5. additionwas added
  6. filtrationthe mixture was filtered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was used for the next step reaction without further purification

Sources & evidence

ORD record
ord-00999698f0bf4cbcb5f002c9b38aa3bf
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

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