Bromotrimethylsilane → (S)-9-[3-Hydroxy-2-(phosphonomethoxy)propoxy]adenine

HRID 6274

Reaction equation

HRID 6274 reaction equation
C([O:3][P:4]([CH2:9][O:10][C@@H:11]([CH2:24][OH:25])[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.C[Si](Br)(C)C>ClCCl>[OH:25][CH2:24][C@H:11]([O:10][CH2:9][P:4]([OH:5])([OH:6])=[O:3])[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]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 54312422(S)-9-[2-(diethoxyphosphorylmethoxy)3-hydroxypropoxy]adenine

Product 1

HCID 54431837(S)-9-[3-Hydroxy-2-(phosphonomethoxy)propoxy]adenineYield 78.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-9-[2-(diethoxyphosphorylmethoxy)-3-hydroxypropoxy]adenine (0.09 g, 0.24 mmol) in dry dichloromethane (3 ml) was added trimethylsilyl bromide (0.31 ml, 2.4 mmol) and the solution stirred at ambient temperature for 4 hours. The solvent was removed under reduced pressure and the residue co-evaporated with acetone/water 1:1 (x3). Crystallisation of the residue from water/acetone gave the title compound as a white solid (0.06 g, 78%), mp. 93°-198° C.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customCrystallisation of the residue from water/acetone

Sources & evidence

ORD record
ord-1700e5b3912a4121a6882d243c1ca8a2
Source dataset
uspto-grants-1993_09
Patent number
US05247085

Linked notes

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