Bromotrimethylsilane → HCID 178496193, compound

HRID 2197463Notes

Reaction equation

HRID 2197463 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([OH:29])[N:6]2[CH2:16][C:17]1[CH:18]=[C:19]([P:23](=[O:28])([OH:27])[O:24]CC)[CH:20]=[CH:21][CH:22]=1.Br[Si](C)(C)C>C(#N)C>[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([OH:29])[N:6]2[CH2:16][C:17]1[CH:18]=[C:19]([P:23](=[O:24])([OH:28])[OH:27])[CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 178476931HCID 178476931, compound

Product 1

HCID 178496193HCID 178496193, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl hydrogen 3-((6-amino-8-hydroxy-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)phenylphosphonate (K) (10 mg, 0.0236 mmol) was suspended in anhydrous acetonitrile (3 mL). Bromotrimethylsilane (0.2 mL) was added. After stirring at room temperature overnight, the mixture was concentrated under vacuum and treated with water (2 mL). Acetonitrile (1 mL) was added and the product was purified by preparative reverse phase HPLC, yielding 3-((6-amino-8-hydroxy-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)phenylphosphonic acid (L) (1.5 mg) as a white solid. 1H-NMR (DMSO) δ: 10.0 (s, 1H), 7.64-7.35 (m, 5H), 6.48 (br, 2H), 4.86 (s, 2H), 4.25 (t, J=4.5 Hz, 2H), 3.57 (t, J=4.5 Hz, 2H), 3.25 (s, 3H). MS: 396 (MH+).

Workup

  1. concentrationthe mixture was concentrated under vacuum
  2. additiontreated with water (2 mL)
  3. additionAcetonitrile (1 mL) was added
  4. customthe product was purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-3d699b98bde4492eac763aa65950c657
Source dataset
uspto-grants-2012_12
Patent number
US08338593B2

Reaction notes

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