tert-Butyldimethylsilyl chloride → HCID 59289304, compound

HRID 2191038Notes

Reaction equation

HRID 2191038 reaction equation
[NH2:1][C:2]1[C:3]2[N:10]=[N:9][N:8]([C@H:11]3[C@:15]([CH3:17])([OH:16])[C@H:14]([OH:18])[C@@H:13]([CH2:19][OH:20])[O:12]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:21][C:22]([Si:25](Cl)([CH3:27])[CH3:26])([CH3:24])[CH3:23]>N1C=CC=CC=1>[NH2:1][C:2]1[C:3]2[N:10]=[N:9][N:8]([C@H:11]3[C@:15]([CH3:17])([OH:16])[C@H:14]([OH:18])[C@@H:13]([CH2:19][O:20][Si:25]([C:22]([CH3:24])([CH3:23])[CH3:21])([CH3:27])[CH3:26])[O:12]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 59289246HCID 59289246, compound

Product 1

HCID 59289304HCID 59289304, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Mixed compound 27.3 (969 mg, 3.4 mmol) with pyridine and concentrated under reduced pressure. The resulting solid was suspended in pyridine 5 mL, treated with TBSCl (615 mg, 4.1 mmol) and the mixture was stirred at r.t. for overnight. The mixture was concentrated down under reduced pressure and water was added to give solid. The suspension was stirred for 30 min, filtered and the solid was dried under reduced pressure to give compound 27.4 (1.33 g, 98% yield).

Workup

  1. concentrationconcentrated under reduced pressure
  2. concentrationThe mixture was concentrated down under reduced pressure and water
  3. additionwas added
  4. customto give solid
  5. stirringThe suspension was stirred for 30 min
  6. filtrationfiltered
  7. customthe solid was dried under reduced pressure

Sources & evidence

ORD record
ord-8cae907372ac41a19d5e544103ccc585
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

Loading…