Water → HCID 178418943, compound

HRID 11758Notes

Reaction equation

HRID 11758 reaction equation
[CH3:1][N:2]([CH3:25])[C:3]1[N:4]=[C:5]([C:20]2[O:21][CH:22]=[CH:23][CH:24]=2)[C:6]2[CH:11]=[CH:10][N:9](COCC[Si](C)(C)C)[C:7]=2[N:8]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[CH3:1][N:2]([CH3:25])[C:3]1[NH:8][C:7]2=[N:9][CH:10]=[CH:11][C:6]2=[C:5]([C:20]2[O:21][CH:22]=[CH:23][CH:24]=2)[N:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 21976419HCID 21976419, compound

Product 1

HCID 178418943HCID 178418943, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N,N-dimethyl4-(2-furyl)-7-(2-trimethylsilylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-amine (370 mg, 0.97 mmol) in THF (3 mL) was treated with tetrabutylammonium fluoride (1 ml, 1-M in THF, 1 mmol), refluxed for 36 h, poured into water, extracted with EtOAc, dried (MgSO4), concentrated in vacuo and purified by chromatography (EtOAc:Heptane, 1:9, alumina) to give the title compound (47 mg, 21%) as a yellow solid.

Workup

  1. temperaturerefluxed for 36 h
  2. extractionextracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by chromatography (EtOAc:Heptane, 1:9, alumina)

Sources & evidence

ORD record
ord-7c74cc044148410e80873354e55e0c9e
Source dataset
uspto-grants-2006_08
Patent number
US07098333B2

Reaction notes

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