Acetone → 9-((2-Phosphonylmethoxy)ethyl)guanine

HRID 266239Notes

Reaction equation

HRID 266239 reaction equation
Br[Si](C)(C)C.C([O:8][P:9]([CH2:14][O:15][CH2:16][CH2:17][N:18]1[CH:26]=[N:25][C:24]2[C:23](=[O:27])[NH:22][C:21]([NH2:28])=[N:20][C:19]1=2)([O:11]CC)=[O:10])C.O.CC(C)=O>CN(C=O)C>[P:9]([CH2:14][O:15][CH2:16][CH2:17][N:18]1[CH:26]=[N:25][C:24]2[C:23](=[O:27])[NH:22][C:21]([NH2:28])=[N:20][C:19]1=2)([OH:10])([OH:11])=[O:8]

Participants

6

Reactant 4

HCID 180AcetoneHCID 962Water2×HCID 76113BromotrimethylsilaneHCID 135404759HCID 135404759, compound

Product 1

HCID 1354094389-((2-Phosphonylmethoxy)ethyl)guanineYield 92.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Bromotrimethylsilane (2.77 g, 18.1 mmol) was added dropwise over 2 min to a solution of 9-(2'-(diethylphosphonomethoxy)ethyl)guanine (0.625 g, 1.80 mmol) in 15 mL of dry DMF at rt under argon in a foil-covered flask. The reaction mixture was stirred at rt for 4 h and then volatiles were removed in vacuo to give a viscous yellow oil. The residue was treated with 5 mL of water, giving immediate formation of a white solid. 5 mL more water was added, followed by 10 mL of acetone; the precipitate was collected by filtration. The crude product was purified by recrystallization from water/ethanol to give 0.483 g of 9-(2-(phosphonomethoxy)ethyl)guanine as white crystals, m.p. >260°.

Workup

  1. customvolatiles were removed in vacuo
  2. customto give a viscous yellow oil
  3. customgiving immediate formation of a white solid
  4. filtrationthe precipitate was collected by filtration
  5. customThe crude product was purified by recrystallization from water/ethanol

Sources & evidence

ORD record
ord-d6e7c801673c4a29a4aec83aa17ff4a2
Source dataset
uspto-grants-1997_07
Patent number
US05650510

Reaction notes

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