Bromotrimethylsilane → HCID 3009294, compound

HRID 373906Notes

Reaction equation

HRID 373906 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[O:11][CH2:12][CH2:13][CH2:14][CH2:15][P:16]([O:21]CC)([O:18]CC)=[O:17])=[C:4]([NH2:24])[N:3]=1.Br[Si](C)(C)C>CN(C)C=O>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[O:11][CH2:12][CH2:13][CH2:14][CH2:15][P:16]([OH:21])([OH:18])=[O:17])=[C:4]([NH2:24])[N:3]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 19808659HCID 19808659, compound

Product 1

HCID 3009294HCID 3009294, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

2,6-Diamino-9-[4-(diethoxyphosphoryl)butoxy]purine (0.07 g, 0.2 mmol) and bromotrimethylsilane (0.26 ml, 2 mmol) were dissolved in dimethylformamide (3 ml) and the reaction mixture was stirred at 23° C. for 4 hr. The solvent was evaporated under vacuum and the residue dissolved in methanol-water solution (8:2). The material crystallised from the solution to give the title compound as colourless crystals (0.05 g, 84%), m.p. 295°-297° C. 1H NMR: δH [(CD3)2SO+D2O] 1.68 (6H, m, CH2CH2CH2P), 4.31 (2H, t, J=6 Hz, NOCH2), 8.35 (1H, s, H-8).

Workup

  1. customThe solvent was evaporated under vacuum
  2. dissolutionthe residue dissolved in methanol-water solution (8:2)
  3. customThe material crystallised from the solution

Sources & evidence

ORD record
ord-df262bece57d4135a81073b60d69bfe9
Source dataset
uspto-grants-1992_11
Patent number
US05166198

Reaction notes

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