Bromotrimethylsilane → HCID 19819549, compound

HRID 1031073Notes

Reaction equation

HRID 1031073 reaction equation
[OH:1][CH2:2][CH:3]([S:16][CH2:17][P:18]([O:23]CC)([O:20]CC)=[O:19])[CH2:4][O:5][N:6]1[CH:14]=[N:13][C:12]2[C:7]1=[N:8][CH:9]=[N:10][C:11]=2[NH2:15].Br[Si](C)(C)C>ClCCl>[OH:1][CH2:2][CH:3]([S:16][CH2:17][P:18]([OH:20])([OH:23])=[O:19])[CH2:4][O:5][N:6]1[CH:14]=[N:13][C:12]2[C:7]1=[N:8][CH:9]=[N:10][C:11]=2[NH2:15]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 19819575HCID 19819575, compound

Product 1

HCID 19819549HCID 19819549, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 9-[3-hydroxy-2-(diethoxyphosphorylmethylthio)propoxy]adenine (0.265 g, 0.67 mmol) in dry dichloromethane (20 ml) was treated with bromotrimethylsilane (1.53 g, 10 mmol) at room temperature and allowed to stand for 6 hours. The solvent was removed under reduced pressure and the residue was dissolved in methanol, before being allowed to stand for 5 minutes. The solution was evaporated to dryness under reduced pressure, re-dissolved in methanol, neutralized with AMBERLITE IR 45 OH resin and filtered and evaporated in vacuo. The residue was crystallised from water to give the title compound (180mg, 80%) as colourless crystals, m.p. 195°-97° C. λmax (H 2 O) 260nm (ε 14,000) υmax (KBr) 3320, 3110, 2920, 1720, 1595, 1550, 1490, 1460, 1405, 1340 and 1300 cm-1 ; δH [(CD3)2SO] 2.70 (2H,d, J 13.5Hz, PCH2S), 3.3 (1 H, m, CH), 3.7 (1H, m, CH ofCH2OH), 3.8 (1H, m, CH of CH2OH), 4.6 (2H, m, CH2O), 7.6 (2H, br s, exchangeable with D2O, NH2), 8.2 (1H, s, 2-H), 8.46 (1H, s, 8-H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in methanol
  3. waitto stand for 5 minutes
  4. customThe solution was evaporated to dryness under reduced pressure
  5. dissolutionre-dissolved in methanol
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was crystallised from water

Sources & evidence

ORD record
ord-b6fc877fdacb4347b40f88c54a5ff9ad
Source dataset
uspto-grants-1992_04
Patent number
US05108994

Reaction notes

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