Bromotrimethylsilane → HCID 136068851, compound

HRID 373910Notes

Reaction equation

HRID 373910 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[O:11][CH:12]([CH2:23][OH:24])[CH2:13][CH2:14][P:15]([O:20]CC)([O:17]CC)=[O:16])=[C:4]([O:25]C)[N:3]=1.Br[Si](C)(C)C>CN(C)C=O>[OH:24][CH2:23][CH:12]([O:11][N:8]1[CH:7]=[N:6][C:5]2[C:4](=[O:25])[NH:3][C:2]([NH2:1])=[N:10][C:9]1=2)[CH2:13][CH2:14][P:15]([OH:20])([OH:17])=[O:16]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 19808603HCID 19808603, compound

Product 1

HCID 136068851HCID 136068851, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-amino-9-[3-(diethoxyphosphoryl)-1-(hydroxymethyl)propoxy]-6-methoxypurine and bromotrimethylsilane (1.98 ml, 15 mmol) in dry dimethylformamide (5ml) was stirred at ambient temperature for 4 hours. The solvent was evaporated and the residue was coevaporated with methanol (5 ml) and acetone:water (1:1) solution. The product was crystallised from acetone:water (1:1) to give the title compound (90 mg, 56%) m.p. 177°-178° C. UV: λmax (H2O) 254 (12400)nm. λsh(H2O) 268 (9365)nm. IR: max (KBr) 3393, 3388, 3347, 3196, 3125, 2929, 2763, 2357, 1700, 1641, 1534, 1474, 1443, 1394, 1317, 1257, 1219, 1162, 1101, 1075, 992, 958, 818, 792, 772 cm-1. 1H NMR δH [CD3)2SO] 1.67-1.94 (4H, m, CH2CH2P), 3.45-3.57 (2H, m, CH2OH), 4.25-4.31 (1H, m, NOCH), 6.59 (2H, br.s, D2O exchangeable NH2), 7.88 (1H, s, H-8), 10.65 (1H, br.s, D2O exchangeable NH), 2.75-6.25 (3H, broad, D2O exchangeable OH, PO(OH)2). Found: C, 33.21; H, 5.01; N, 21.42%. C9H14N5O6P 0.4 H2O requires: C, 33.11; H, 4.56; N, 21.45%. m/z (FAB+ve ion, thioglycerol) MH+ 320.

Workup

  1. customThe solvent was evaporated
  2. customThe product was crystallised from acetone:water (1:1)

Sources & evidence

ORD record
ord-3f3d88d3c5a546ca8d335a5020e58b0d
Source dataset
uspto-grants-1992_11
Patent number
US05166198

Reaction notes

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