Potassium Carbonate → 6-chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-purine

HRID 1894668Notes

Reaction equation

HRID 1894668 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23]>CN(C=O)C>[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 53592776-Chloropurine

Product 1

HCID 108698516-chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-purineYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Chloropurine (5.0 g, 32 mmol) in DMF (75 mL) was treated with potassium carbonate (9.0 g, 65 mmol) and [2-(chloromethoxy)ethyl]trimethylsilane (7.0 g, 42 mmol) and stirred for 2 h. The reaction mixture was partitioned between EtOAc and water. The organic layer was dried (MgSO4), concentrated in vacuo and purified by column chromatography (SiO2, 20% EtOAc in isohexane) to give the title compound (4.9 g, 54%) as an off-white solid. δH (CDCl3) 8.82 (1H, s), 8.32 (1H, s), 5.71 (2H, s), 3.71-3.61 (2H, m), 1.03-0.93 (2H, m), 0.00 (9H, s).

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. custompurified by column chromatography (SiO2, 20% EtOAc in isohexane)

Sources & evidence

ORD record
ord-830607af4a78429e83f58b137d8dbdfe
Source dataset
uspto-grants-2013_08
Patent number
US08513284B2

Reaction notes

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