Bromotrimethylsilane → HCID 19808624, compound

HRID 373909Notes

Reaction equation

HRID 373909 reaction equation
[OH:1][CH:2]([CH2:15][CH2:16][P:17]([O:22]CC)([O:19]CC)=[O:18])[CH2:3][O:4][N:5]1[CH:13]=[N:12][C:11]2[C:6]1=[N:7][CH:8]=[N:9][C:10]=2[NH2:14].Br[Si](C)(C)C>CN(C)C=O>[OH:1][CH:2]([CH2:15][CH2:16][P:17]([OH:19])([OH:22])=[O:18])[CH2:3][O:4][N:5]1[CH:13]=[N:12][C:11]2[C:6]1=[N:7][CH:8]=[N:9][C:10]=2[NH2:14]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 19808644HCID 19808644, compound

Product 1

HCID 19808624HCID 19808624, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 9-[2-hydroxy-4-(diethoxyphosphoryl)butoxy]adenine (0.50 g, 0.14 mmol) and bromotrimethylsilane (0.184 ml, 1.4 mmol) in dry dimethylformamide (3 ml) was stirred at room temperature for 3 hours. The solvent was then evaporated and the residue was coevaporated with dimethylformamide (2×5 ml) and methanol:water (9:1) solution. The product crystallised from water:methanol (9:1) solution to give the title compound (35 mg, 83%); m.p. 265°-267° C. 1H NMR: δH [(CD3)2SO] 1.6 (4H, m, CH3CH2CH2P), 3.8 (1H, m, CHCH2CH2P) 4.25 (2H, m, OCH2) 7.41 (2H, br. s, D2O exchangeable, NH2), 8.16 (1H, s, H-2), 8.36 (1H, s, H-8). Found: C, 35.78; H, 4.52; N, 22.25%. C9H17N5PO5 requires: C, 35.65; H, 4.65; N, 23.1%.

Workup

  1. customThe solvent was then evaporated
  2. customThe product crystallised from water:methanol (9:1) solution

Sources & evidence

ORD record
ord-a7b60c1ef7834e038259dd1a48f1ba74
Source dataset
uspto-grants-1992_11
Patent number
US05166198

Reaction notes

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