Bromotrimethylsilane → HCID 131717652, compound

HRID 373908Notes

Reaction equation

HRID 373908 reaction equation
C([O:3][P:4]([CH2:9][CH2:10][CH2:11][O:12][N:13]1[CH:21]=[N:20][C:19]2[C:14]1=[N:15][CH:16]=[N:17][C:18]=2[NH2:22])([O:6]CC)=[O:5])C.[Br:23][Si](C)(C)C>ClCCl>[BrH:23].[P:4]([CH2:9][CH2:10][CH2:11][O:12][N:13]1[CH:21]=[N:20][C:19]2[C:14]1=[N:15][CH:16]=[N:17][C:18]=2[NH2:22])([OH:6])([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 19808662HCID 19808662, compound

Product 1

HCID 131717652HCID 131717652, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 9-[3-(diethoxyphosphoryl)propoxy]adenine (300 mg, 0.9 mmol) in dry dichloromethane (10 ml), was added bromotrimethylsilane (0.6 ml, 4.5 mmol). After 2 hours at ambient temperature, the solution was evaporated to dryness, the residue treated with methanol and the solution evaporated to dryness again. The solid residue was crystallised from methanol-acetone to afford 9-(3-phosphonopropoxy)adenine, hydrobromide salt, (80 mgs, 24%) m.p. 175°-180° C.. UV: λmax (MeOH) 259 (ε14,050) nm. IR: υmax (KBr) 1692, 1588, 1451, 1416, 1335, 1220, 1061, 1004, 952 cm-1. 1H NMR: δH [(CD3)2SO] 1.6-1.95 (4H, m, CH2CH2P), 4.47 (2H, t, J=6.5 Hz, N--OCH2), 8.46 (1H, s), 8.76 (1H, s), 7.0-10.0 (5H, broad, D2O exchangeable). Found: C, 27.29; H, 3.80; N, 19.64; Br, 21.52%. C8H13N5O4PBr requires: C, 27.13; H, 3.70; N, 19.78. Br, 22.50%.

Workup

  1. customthe solution was evaporated to dryness
  2. additionthe residue treated with methanol
  3. customthe solution evaporated to dryness again
  4. customThe solid residue was crystallised from methanol-acetone

Sources & evidence

ORD record
ord-9e6531ad4c1946838e28b83502ea1b99
Source dataset
uspto-grants-1992_11
Patent number
US05166198

Reaction notes

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