Water → HCID 178483026, compound

HRID 271255Notes

Reaction equation

HRID 271255 reaction equation
[CH3:1][N:2]([CH3:25])[C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2COCC[Si](C)(C)C)=[C:5]([C:20]2[O:21][CH:22]=[CH:23][CH:24]=2)[N:4]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[CH3:1][N:2]([CH3:25])[C:3]1[NH:4][C:5]([C:20]2[O:21][CH:22]=[CH:23][CH:24]=2)=[C:6]2[C:10]([N:11]=1)=[N:9][CH:8]=[N:7]2

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 59835007HCID 59835007, compound

Product 1

HCID 178483026HCID 178483026, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N,N-dimethyl-6-(2-furyl)-9-(2-trimethylsilylethoxymethyl)-9H-purine-2-amine (200 mg, 0.56 mmol) in THF (5 mL) was treated with tetra-n butylammonium fluoride (1-M in THF, 0.67 mL, 0.67 mmol), refluxed for 4 h, cooled, poured into water and extracted with EtOAc. The combined organic phase was dried (MgSO4), concentrated in vacuo and purified by chromatography (SiO2; EtOAc) to give the title compound (98 mg, 76%) as a pale yellow solid.

Workup

  1. temperaturerefluxed for 4 h
  2. temperaturecooled
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic phase was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. custompurified by chromatography (SiO2; EtOAc)

Sources & evidence

ORD record
ord-b918c25d4a1741a4b6f9856728e45684
Source dataset
uspto-grants-2008_11
Patent number
US07452894B2

Reaction notes

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