Bromotrimethylsilane → HCID 136403407, compound

HRID 373911Notes

Reaction equation

HRID 373911 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[O:11][CH2:12][CH:13]([OH:23])[CH2:14][P:15]([O:20]CC)([O:17]CC)=[O:16])=[C:4]([O:24]C)[N:3]=1.Br[Si](C)(C)C>CN(C)C=O>[OH:23][CH:13]([CH2:14][P:15]([OH:17])([OH:20])=[O:16])[CH2:12][O:11][N:8]1[CH:7]=[N:6][C:5]2[C:4](=[O:24])[NH:3][C:2]([NH2:1])=[N:10][C:9]1=2

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 19808656HCID 19808656, compound

Product 1

HCID 136403407HCID 136403407, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-amino-6-methoxy-9-[2-hydroxy-3-(diethoxyphosphoryl)propoxy]purine (70 mg, 0.182 mmol) and bromotrimethylsilane (0.4 ml, 3 mmol) in dimethylformamide (3 ml) was stirred at 23° C. for 3 hours. The solvent was evaporated and the residue was coevaporated with dimethylformamide (2×5 ml) and methanol:water (9.1) solution (1×5 ml). Crystallization from water:methanol (9:1) gave the title compound (34 mg, 62%); m.p. 258° C.-260° C. 1H NMR: δH [(CD3)2SO] 1.80 (2H, m, PCH2), 4.2 (3H, m, PCH2CHCH2), 6.62 (2H, br.s, D2O exchangeable NH2), 7.90 (1H, s, H-8), 10.64 (1H, br.s, D2O exchangeable NH). Found: C, 31.34; H, 4.05; N, 22.61%. C 8 H12N5O6P requires: C, 31.48; H, 3.96; N, 22.95%.

Workup

  1. customThe solvent was evaporated
  2. customCrystallization from water:methanol (9:1)

Sources & evidence

ORD record
ord-291c790bc4314582b2a0afa8dd52e4f7
Source dataset
uspto-grants-1992_11
Patent number
US05166198

Reaction notes

Loading…