Potassium Carbonate → HCID 178504248, compound

HRID 545657Notes

Reaction equation

HRID 545657 reaction equation
[Cl:1][C:2]1[NH:10][CH:9]=[N:8][C:7]2[C:3]=1[N: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[NH:10][CH2:9][N:8]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:7]2[C:3]=1[N:4]=[CH:5][N:6]=2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178478416HCID 178478416, compound

Product 1

HCID 178504248HCID 178504248, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.31 g (2.0 mmol) of 6-chloro-1H-purine and 0.83 g (6.0 mmol) of potassium carbonate in 15 mL of DMF was stirred at 25° C. for 20 min. under argon. To it, 0.53 mL (3.0 mmol) of 1-(chloromethoxy)-2-(trimethylsilyl)ethane (SEM-Cl) was added via syringe, the solution was stirred for 9 h, filtered through Celite, and the filtrate was diluted with diethyl ether, washed with water, and brine, dried (MgSO4), concentrated, and column chromatographed on silica gel using a gradient mixture of hexane and ethyl acetate to give 0.35 g (61% yield) of 115 and 0.08 g (14% yield) of 6-chloro-3-[(2-trimethylsilylethoxy) methyl]-1H-purine (117). Compound 115: mp 33-34° C.; NMR δ 8.70 (s, 1H), 8.24 (s, 1H), 5.62 (s, 2H, NCH2O), 3.60 (t, J=8 Hz, 2H, CH2O), 0.94 (t, J=8 Hz, 2H, CH2Si), −0.12 (s, 9H, MeSi); 13C NMR δ 152.4, 152.2, 151.3, 145.4, 131.5, 72.7 (CN), 67.8 (CO), 17.8, 21.4 (CSi).

Workup

  1. filtrationfiltered through Celite
  2. additionthe filtrate was diluted with diethyl ether
  3. washwashed with water, and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customcolumn chromatographed on silica gel using
  7. additiona gradient mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-0ae8cb57c75b43a8975057bed9f9e6be
Source dataset
uspto-grants-2011_05
Patent number
US07935726B1

Reaction notes

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