Bromotrimethylsilane → HCID 19993510, compound

HRID 345077Notes

Reaction equation

HRID 345077 reaction equation
Br[Si](C)(C)C.C([O:8][P:9]([CH2:14][O:15][CH2:16][CH2:17][CH2:18][O:19][N:20]1[CH:28]=[N:27][C:26]2[C:21]1=[N:22][CH:23]=[N:24][C:25]=2[NH2:29])([O:11]CC)=[O:10])C>ClCCl>[P:9]([CH2:14][O:15][CH2:16][CH2:17][CH2:18][O:19][N:20]1[CH:28]=[N:27][C:26]2[C:21]1=[N:22][CH:23]=[N:24][C:25]=2[NH2:29])([OH:11])([OH:10])=[O:8]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 19993526HCID 19993526, compound

Product 1

HCID 19993510HCID 19993510, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Bromotrimethylsilane (0.55 ml, 4.18 mmol) was added dropwise to a solution of 9-[3-(diethoxyphosphorylmethoxy)propoxy]adenine (0.25 g, 0.70 mmol) in dry dichloromethane (2 ml) and the reaction stirred under nitrogen at 25° C. for 3 h. After concentration in vacuo the residue was co-evaporated three times with methanol. Reverse-phase chromatography, eluting with 5% aqueous methanol gave 9-[3-(phosphonomethoxy)propoxy]adenine (152 mg, 71%) as a white solid; m.p. 246°-249° C. νmax (KBr) 3320, 3084, 1700, 1079 cm-1 ; δH [(CD3)2SO] 1.94(2H, t, J6.3 Hz, CH2CH2CH2), 3.56(2H, d, J8.5 Hz, CH2P), 3.70(2H, t, J6 Hz, CH2OCH2P), 4.43(2H, t, J6 Hz, NOCH2), 7.40(2H, br s, D2O exchangeable, NH2), 8.15(1H, s, H-2), 8.43(1H, s, H-8); Found: C, 34.15; H, 5.12; N, 21.89%; C9H14N5O5P.0.8H2O requires: C, 34.03; H, 4.95; N, 22.04%.

Workup

  1. concentrationAfter concentration in vacuo the residue
  2. washReverse-phase chromatography, eluting with 5% aqueous methanol

Sources & evidence

ORD record
ord-2e92c1d3192442ddbe011771d9960cba
Source dataset
uspto-grants-1991_10
Patent number
US05055458

Reaction notes

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