Bromotrimethylsilane → HCID 136051123, compound

HRID 373903Notes

Reaction equation

HRID 373903 reaction equation
C([O:3][P:4]([CH2:9][CH2:10][CH2:11][O:12][N:13]1[CH:21]=[N:20][C:19]2[C:18](=[O:22])[NH:17][C:16]([NH2:23])=[N:15][C:14]1=2)([O:6]CC)=[O:5])C.Br[Si](C)(C)C>CN(C=O)C>[P:4]([CH2:9][CH2:10][CH2:11][O:12][N:13]1[CH:21]=[N:20][C:19]2[C:18](=[O:22])[NH:17][C:16]([NH2:23])=[N:15][C:14]1=2)([OH:6])([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 136116075HCID 136116075, compound

Product 1

HCID 136051123HCID 136051123, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 9-[3-(diethoxyphosphoryl)propoxy]guanine (110 mg, 0.32 mmol) in dry DMF (2 ml) was added bromotrimethylsilane (0.25 ml, 1.91 mmol). The solution was left at ambient temperature for 24 hours, evaporated to dryness under reduced pressure, the residue dissolved in methanol and the solution evaporated to dryness again. The resulting solid was washed again with methanol. The solid was suspended in water (2 ml) and 0.880 NH3 added to obtain a solution. The solution was passed through a column of Dowex 50W-X8(H) ion-exchange resin (previously washed with water) and the column eluted with water. The UV absorbing fractions were collected and evaporated to dryness to give the title compound as a white solid (45 mg, 50%), m.p. >300° C. UV: λmax (EtOH) 255 mm. IR: υmax (KBr) 3700-2100 (broad), 1743, 1700, 1662, 1552, 1474, 1419, 1327, 1240, 1164, 1080, 1029, 1011, 969, 775, 694 cm-1 . 1H NMR: δH ((CD3)2SO) 1.6-1.9 (4H, m, CH2CH2P), 4.28 (2H, t, J=7 Hz, O--CH2), 6.59 (2H, bs, D2O exchangeable, NH2), 7.92 (1H, s, H-8), 10.63 (1H, bs, D2O exchangeable, NH), 2.5-4.5 (2H, broad, D2O exchangeable, PO(OH)2). C8H12N5O5P. 0.75 H2O requires C, 31.74; H, 4.34; N, 23.14%. Found: C, 31.96; H, 4.13; N, 23.01%.

Workup

  1. customevaporated to dryness under reduced pressure
  2. dissolutionthe residue dissolved in methanol
  3. customthe solution evaporated to dryness again
  4. washThe resulting solid was washed again with methanol
  5. addition0.880 NH3 added
  6. customto obtain a solution
  7. washpreviously washed with water) and the column
  8. washeluted with water
  9. customThe UV absorbing fractions
  10. customwere collected
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-a01b704fedf24cb7b7fc9ed80a477336
Source dataset
uspto-grants-1992_11
Patent number
US05166198

Reaction notes

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