Bromotrimethylsilane → HCID 6474552, compound

HRID 1708102Notes

Reaction equation

HRID 1708102 reaction equation
C([O:4][P:5](/[CH:11]=[CH:12]/[CH:13]([CH2:26][OH:27])[CH2:14][O:15][N:16]1[CH:24]=[N:23][C:22]2[C:17]1=[N:18][CH:19]=[N:20][C:21]=2[NH2:25])([O:7]C(C)C)=[O:6])(C)C.C[Si](Br)(C)C>CN(C)C=O>[OH:27][CH2:26][CH:13](/[CH:12]=[CH:11]/[P:5]([OH:6])([OH:7])=[O:4])[CH2:14][O:15][N:16]1[CH:24]=[N:23][C:22]2[C:17]1=[N:18][CH:19]=[N:20][C:21]=2[NH2:25]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 10318725HCID 10318725, compound

Product 1

HCID 6474552HCID 6474552, compoundYield 15,106.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (E)-9-[4-(diisopropoxyphosphoryl) -2(hydroxymethyl)but-3-enyloxy]adenine (0.25 g, 0.63 mmol) in anhydrous N,N-dimethylformamide (5 ml) under nitrogen was treated with trimethylsilylbromide (1.24 ml, 9.4 mmol) at 0° C. and the solution stirred for 18 h at room temperature. The solvent was removed in vacuo coevaporatng several times with methanol and toluene and the residue chromatographed on C18 reverse phase silica gel eluting with water to give (E)-9-(2-hydroxymethyl-4-phosphonobut-3-enyloxy) adenine as a solid (30 g, 17%); λmax (H2O) 260 nm (13711); υmax (KBr) 3434, 1717, 1690, 1653, 1640, 1472, and 1414 cm-1 ; δH [(CD3)2SO] 2.78 (1H, m, CH), 3.38 (3H, br.s, 3×OH, H2O), 3.60 (2H, m, CH2OH) , 4.48 (2H, m, CH2ON), 5.99 (1H, m, PCH=CH), 6.48 (1H, m, PCH=CH), 7.37 (2H, br.s, D2O exchangeable NH2), 8.14 (1H, s, H-2/H-8), 8.34 (1H, s, H-2/H-8) (Found: C, 36.50; H, 4.45; N, 20.49%. C10H14N5O5P.0.9H2O requires C, 36.24; H, 4.77; N, 21.13%).

Workup

  1. customThe solvent was removed in vacuo coevaporatng several times with methanol and toluene
  2. customthe residue chromatographed on C18 reverse phase silica gel eluting with water

Sources & evidence

ORD record
ord-bb4c91016c1e4458a342c8401ad79718
Source dataset
uspto-grants-1994_10
Patent number
US05356886

Reaction notes

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