2-Methylaziridine → HCID 14006570, compound

HRID 2417680Notes

Reaction equation

HRID 2417680 reaction equation
Cl[C:2]1[C:3]2[N:11]([CH2:12][CH3:13])[N:10]=[C:9]([CH3:14])[C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1.C([N:17]([CH2:20][CH3:21])[CH2:18]C)C.CC1CN1>C(Cl)Cl>[CH2:12]([N:11]1[C:3]2[C:2]([N:17]3[CH2:18][CH:20]3[CH3:21])=[N:7][C:6]([CH3:8])=[N:5][C:4]=2[C:9]([CH3:14])=[N:10]1)[CH3:13]

Participants

5

Reactant 3

HCID 63772-MethylaziridineHCID 8471TriethylamineHCID 133384097-Chloro-1-ethyl-3,5-dimethyl-1H-pyrazolo[4,3-d]pyrimidine

Product 1

HCID 14006570HCID 14006570, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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. washThe solution is washed with saturated sodium bicarbonate solution
  2. dry with materialdried (MgSO4)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-a99cc5e8ac5a4064b9ccfae85da0e469
Source dataset
uspto-grants-1984_09
Patent number
US04469868

Reaction notes

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