Bromotrimethylsilane → 9-(2-(Phosphonomethoxy)ethoxy)adenine

HRID 6260

Reaction equation

HRID 6260 reaction equation
C([O:3][P:4]([CH2:9][O: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.C[Si](Br)(C)C>ClCCl>[P:4]([CH2:9][O: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 100431699-[2-(Diethoxyphosphorylmethoxy)ethoxy]adenine

Product 1

HCID 4731399-(2-(Phosphonomethoxy)ethoxy)adenine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 9-[2-(diethoxyphosphorylmethoxy)ethoxy]adenine (0.63 g, 1.83 mmol) in dry dichloromethane (10 ml) was added trimethylsilyl bromide (1.45 ml, 11 mmol) and the solution stirred at ambient temperature for 2 hours. The solvent was removed under reduced pressure and the residue dissolved in methanol (10 ml). The solvent was evaporated and the residue again dissolved in methanol and solvent evaporated to give a solid residue. Crystallisation from methanol: acetone gave the title compound which was recrystallised from methanol: water (0.24 g, 45%), m.p. 241°-244° C. UV: λmax (EtOH) 259 nm (ε 13,500); IR: νmax (KBr) 3428, 3312, 3084, 1685, 1644, 1612, 1484, 1462, 1455, 1336, 1294, 1278, 1255, 1215, 1195, 1104, 1060, 1046, 1033, 955, 934, 892 cm-1. 1H NMR: δH [(CD3)2SO]3.64 (2H,d,J=8.2 Hz, OCH2P), 3.82 (2H,m,N-OCH2CH2O), 4.50 (2H,m, N-OCH2CH2), 7.42 (2H, br.s, D2O exchangeable NH2), 8.15 (1H,s,H-8), 8.38 (1H,s,H-2) 10.0-4.5 (2H,broad, D2O exchangeable PO(OH )2). Found: C,32.84; H,4.41; N: 23.74%. C8H12N5O5P. H2O requires: C,33.01; H,4.19; N:24.06%.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in methanol (10 ml)
  3. customThe solvent was evaporated
  4. dissolutionthe residue again dissolved in methanol
  5. customsolvent evaporated
  6. customto give a solid residue
  7. customCrystallisation from methanol

Sources & evidence

ORD record
ord-5ee968f7cd244e5c82b70d125ecc7106
Source dataset
uspto-grants-1993_09
Patent number
US05247085

Linked notes

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