Tetrabutylammonium Hydroxide → Tetrabutylammonium

HRID 363716Notes

Reaction equation

HRID 363716 reaction equation
[I:1][C:2]1[N:10]=[C:9]([NH2:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2.[OH-].[CH2:13]([N+:17]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH3:16]>ClCCl>[I:1][C:2]1[N:10]=[C:9]([NH2:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2.[CH2:26]([N+:17]([CH2:13][CH2:14][CH2:15][CH3:16])([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:22][CH2:23][CH2:24][CH3:25])[CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 2

HCID 2723671Tetrabutylammonium HydroxideHCID 178508570HCID 178508570, compound

Product 2

HCID 16028TetrabutylammoniumHCID 178508570HCID 178508570, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Iodo-9H-purin-2-amine (133 g., 510 mmole) ground up in a mortar and pestle was washed into a 2 liter pot with 1.5 liter dichloromethane. Aqueous tetrabutylammonium hydroxide (1.53M, 333 ml., 510 mmole) was added and the mixture was stirred mechanically for 30 minutes. The mixture was then filtered through Celite, washed five times with methylene chloride, and the methylene chloride layer was separated, dried (MgSO4), and evaporated. The residue was evaporated from toluene (300 ml.). The residue was taken up in 1 liter of ethyl acetate and heated briefly to form a two-phase mixture. This mixture was stirred mechanically at room temperature for 30 minutes. The resulting crystals were filtered, washed with ethyl acetate, and dried under vacuum overnight to give 213.5 g. of product. 20 g. of this material was dried further overnight at 50° C. under vacuum over phosphorus pentoxide to give 6-iodo-9H-purin-2-amine, ion (1-), tetrabutylammonium (1:1) salt; m.p. 114°-116° C.

Workup

  1. filtrationThe mixture was then filtered through Celite
  2. washwashed five times with methylene chloride
  3. customthe methylene chloride layer was separated
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was evaporated from toluene (300 ml.)
  7. temperatureheated briefly
  8. customto form a two-phase mixture
  9. stirringThis mixture was stirred mechanically at room temperature for 30 minutes
  10. filtrationThe resulting crystals were filtered
  11. washwashed with ethyl acetate
  12. customdried under vacuum overnight
  13. customto give 213.5 g
  14. dry with materialof this material was dried further overnight at 50° C. under vacuum over phosphorus pentoxide

Sources & evidence

ORD record
ord-26415019035c4094b8541df7067cc713
Source dataset
uspto-grants-1999_02
Patent number
US05874578

Reaction notes

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