Bromotrimethylsilane → 9-[2-(Phosphonomethylthio)ethoxy)adenine

HRID 1031072Notes

Reaction equation

HRID 1031072 reaction equation
C([O:3][P:4]([CH2:9][S: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>ClCCl>[P:4]([CH2:9][S: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:6])([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 198195779-[2-(Diethoxyphosphorylmethylthio)-ethoxy]adenine

Product 1

HCID 198195489-[2-(Phosphonomethylthio)ethoxy)adenineYield 72.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 9-[2-(diethoxyphosphorylmethylthio)-ethoxy]adenine (0.1 g, 0.27 mmol) in dry dichloromethane at room temperature was treated with bromotrimethylsilane (0.46 g, 30 mmol) and allowed to stand for 3 hours. The solvent was evaporated under reduced pressure and the residue was dissolved in methanol and allowed to stand for 5 minutes. The solvent was removed in vacuo and the residue was crystallised from water to give the title compound (0.06 g, 71%) as colourless crystals, m.p. 211°-13° C.; υmax (KBr) 3060, 2960, 1695, 1600, 1555, 1470, 1450, 1400, 1350 and 1300 cm-1 ; 6H [(CD3)2SO] 2.7 (2H, d J 13Hz. PCH2S), 3.1 (2H, t J 6.5Hz, CH2O), 4.6 (2H, t J 6.5Hz CH2S), 7.4 (2H, br.s, exchangeable with D2O, NH2), 8.15 (1 H, s, 2-H), 8.4 (1H, s, 8-H). (Found: C, 31.58; H, 3.92; N, 23.26%. C8H12N5O4PS requires C, 31.47; H, 3.96; N, 22.95%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in methanol
  3. waitto stand for 5 minutes
  4. customThe solvent was removed in vacuo
  5. customthe residue was crystallised from water

Sources & evidence

ORD record
ord-afef4dc41315460eb9276d5f1250fbee
Source dataset
uspto-grants-1992_04
Patent number
US05108994

Reaction notes

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