Sodium Iodide → HCID 13338395, compound

HRID 2417681Notes

Reaction equation

HRID 2417681 reaction equation
[CH2:1]([N:3]1[C:11]2[C:10]([N:12]3[CH2:14][CH:13]3[CH3:15])=[N:9][C:8]([CH3:16])=[N:7][C:6]=2[C:5]([CH3:17])=[N:4]1)[CH3:2].[I-].[Na+]>CC(C)=O>[CH2:1]([N:3]1[C:11]2[C:10]3[N:9]([CH2:15][CH:13]([CH3:14])[N:12]=3)[C:8]([CH3:16])=[N:7][C:6]=2[C:5]([CH3:17])=[N:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 14006570HCID 14006570, compound

Product 1

HCID 13338395HCID 13338395, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4.2 g (0.02 mol) of 7-chloro-3,5-dimethyl-1-ethyl-1H-pyrazolo[4,3-d]pyrimidine (Ex. 16), 3 ml of triethylamine and 5 ml of 2-methylaziridine in 100 ml of methylene dichloride is allowed to stand at room temperature 20 hours. The solution is washed with saturated sodium bicarbonate solution, dried (MgSO4), and evaporated in vacuo to give 4 g of 1-ethyl-3,5-dimethyl-7-(2-methylaziridinyl)pyrazolo[4,3-d]pyrimidine as an oil, characterized by IR and NMR. The aziridine (4 g, 0.017 mol) in 40 ml of acetone is refluxed 1.5 hours with 3 g (0.02 mol) of sodium iodide. The solution is evaporated in vacuo. The residue is partitioned in 100 ml of methylene dichloride and 30 ml of 20% sodium carbonate solution. The organic layer is separated, dried over magnesium sulfate, and the solvent is evaporated in vacuo to give 2.8 g (71%) of the title compound, mp 145°-147° C. from ethyl acetate-pet ether.

Workup

  1. customThe solution is evaporated in vacuo
  2. customThe residue is partitioned in 100 ml of methylene dichloride
  3. customThe organic layer is separated
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent is evaporated in vacuo

Sources & evidence

ORD record
ord-17613a3c6b5e411dbb59b1b870c16ba1
Source dataset
uspto-grants-1984_09
Patent number
US04469868

Reaction notes

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