Bromotrimethylsilane → Tenofovir

HRID 1890236

Reaction equation

HRID 1890236 reaction equation
C([O:3][P:4]([CH2:9][O:10][C@H:11]([CH3:23])[CH2:12][N:13]1[CH:21]=[N:20][C:19]2[C:14]1=[N:15][CH:16]=[N:17][C:18]=2[NH2:22])([O:6]CC)=[O:5])C.Br[Si](C)(C)C>C(#N)C>[P:4]([CH2:9][O:10][C@H:11]([CH3:23])[CH2:12][N:13]1[CH:21]=[N:20][C:19]2[C:14]1=[N:15][CH:16]=[N:17][C:18]=2[NH2:22])([OH:5])([OH:6])=[O:3]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 10947889Diethyl P-(((1R)-2-(6-amino-9H-purin-9-yl)-1-methylethoxy)methyl)phosphonate

Product 1

HCID 464205Tenofovir

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a reaction vessel was added stepwise the product (D) of step (4), acetonitrile and Bromotrimethylsilane, the mixture was refluxed while stirring until the completion of the reaction, volatile liquid was removed under vacuum, the resultant residue was then dissolved in a suitable amount of water, and the resulting solution was adjusted to pH 3.0˜3.5 to give the product 9-[(R)-2-(phosphonomethoxy)propyl]adenine (PMPA). Furthermore, dichloromethane or chloroform could be used as reaction solvent and iodotrimethylsilane or chlorotrimethylsilane/potassium iodide as the deprotection agent.

Workup

  1. temperaturethe mixture was refluxed
  2. customwas removed under vacuum
  3. dissolutionthe resultant residue was then dissolved in a suitable amount of water

Sources & evidence

ORD record
ord-8714acba1ab1429395fcb886b63619c7
Source dataset
uspto-grants-2013_08
Patent number
US08507463B2

Linked notes

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