Bromotrimethylsilane → HCID 461343, compound

HRID 373907Notes

Reaction equation

HRID 373907 reaction equation
C([O:3][P:4]([CH2:9][CH2:10][CH2:11][CH2:12][O:13][N:14]1[CH:22]=[N:21][C:20]2[C:15]1=[N:16][CH:17]=[N:18][C:19]=2[NH2:23])([O:6]CC)=[O:5])C.Br[Si](C)(C)C>CN(C)C=O>[P:4]([CH2:9][CH2:10][CH2:11][CH2:12][O:13][N:14]1[CH:22]=[N:21][C:20]2[C:15]1=[N:16][CH:17]=[N:18][C:19]=2[NH2:23])([OH:5])([OH:6])=[O:3]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 19808605HCID 19808605, compound

Product 1

HCID 461343HCID 461343, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

9-[4-(Diethoxyphosphoryl)butoxy]adenine (0.165 g, 0.48 mmol) and bromotrimethylsilane (0.62 ml, 4.8 mmol) were dissolved in dimethylformamide (5 ml) and the reaction mixture was stirred at 23° C. for 90 min. The solvent was evaporated and the residue dissolved in methanol-water solution (9:1). The material crystallised from the solution to give the title compound as colourless crystals (96 mg, 70%), m.p. 265°-268° C. 1H NMR: δH [CD3)2SO] 1.77 (6H, m, CH2CH2CH2P), 4.45 (2H, t, J=6 Hz, NOCH2), 7.46 (2H, br.s., D2O exchangeable, NH2), 8.24 (1H, s), 8.48 (1H, s).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in methanol-water solution (9:1)
  3. customThe material crystallised from the solution

Sources & evidence

ORD record
ord-a542ba71c4e24e658e22247df5cb9d46
Source dataset
uspto-grants-1992_11
Patent number
US05166198

Reaction notes

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