Sodium Iodide → Rac-2-(methylamino)-1-pyrimidin-2-ylethanol

HRID 23698Notes

Reaction equation

HRID 23698 reaction equation
Cl[CH2:2][CH:3]([C:5]1[N:10]=[CH:9][CH:8]=[CH:7][N:6]=1)[OH:4].[I-].[Na+].[CH3:13][NH2:14]>CO>[CH3:13][NH:14][CH2:2][CH:3]([C:5]1[N:10]=[CH:9][CH:8]=[CH:7][N:6]=1)[OH:4]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6329MethylamineHCID 22563217HCID 22563217, compound

Product 1

HCID 10171256Rac-2-(methylamino)-1-pyrimidin-2-ylethanolYield 47.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a pressure bottle was placed 2-chloro-1-pyrimidin-2-ylethanol (3.525 g, 22.24 mmol), sodium iodide (0.344 g, 2.29 mmol) and a 2M. methylamine solution (160 ml, 320 mmol) in methanol. The bottle was sealed and heated at 62° for 17 hr. The solvent was evaporated and the residue stirred with 10% MeOH—CHCl3. Filtration and evaporation gave a dark oil that was chromatographed over silica gel (90 g) eluting with 5-10% MeOH—CH2Cl2 containing 1% triethylamine The product was obtained as an amber oil (1.625 g).

Workup

  1. customThe bottle was sealed
  2. temperatureheated at 62° for 17 hr
  3. customThe solvent was evaporated
  4. filtrationFiltration and evaporation
  5. customgave a dark oil that
  6. customwas chromatographed over silica gel (90 g)
  7. washeluting with 5-10% MeOH—CH2Cl2 containing 1% triethylamine The product

Sources & evidence

ORD record
ord-db4df481182b4e45adbff5ce1c0d179a
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Reaction notes

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