Bromotrimethylsilane → HCID 135542258, compound

HRID 1463786Notes

Reaction equation

HRID 1463786 reaction equation
C([O:4][P:5]([CH2:11][O:12][C@@H:13]([CH2:26][OH:27])[CH2:14][N:15]1[CH:23]=[N:22][C:21]2[C:20](=[O:24])[NH:19][C:18]([NH2:25])=[N:17][C:16]1=2)([O:7]C(C)C)=[O:6])(C)C.C[Si](Br)(C)C>C(#N)C>[OH:27][CH2:26][C@H:13]([O:12][CH2:11][P:5]([OH:6])([OH:7])=[O:4])[CH2:14][N:15]1[CH:23]=[N:22][C:21]2[C:20](=[O:24])[NH:19][C:18]([NH2:25])=[N:17][C:16]1=2

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 135678256HCID 135678256, compound

Product 1

HCID 135542258HCID 135542258, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (R)9-[2-[(diisopropylphosphono)methoxy]3-hydroxypropyl]guanine (0.20 g, 0.50 mmol) in 5 mL of dry acetonitrile was treated with trimethylsilylbromide (0.99 g, 6.45 mmol) under nitrogen atmosphere. The resulting solution was protected from light and stirred at room temperature for 14 hours. The solvent was removed under reduced pressure, and the residue was dried under vacuum. To the residue, water (1 mL) and acetone (4 mL) were added. The mixture was stirred at room temperature overnight and then the solvent removed. The residue was triturated with methylene chloride and filtered. The collected solid was recrystallized from water-methanol to give 127 mg (80% yield) of the title compound as white crystals: mp 249° C. (dec.).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was dried under vacuum
  3. additionTo the residue, water (1 mL) and acetone (4 mL) were added
  4. stirringThe mixture was stirred at room temperature overnight
  5. customthe solvent removed
  6. customThe residue was triturated with methylene chloride
  7. filtrationfiltered
  8. customThe collected solid was recrystallized from water-methanol

Sources & evidence

ORD record
ord-677f7db0476e4a0cb33bbb721b8825fa
Source dataset
uspto-grants-1994_04
Patent number
US05302585

Reaction notes

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