2,2,2-Trifluoroethanol → 5-Cyclobutylaminomethyl-pyrazin-2-ylamine

HRID 1431129Notes

Reaction equation

HRID 1431129 reaction equation
[CH:1]1([NH:5][CH2:6][C:7]2[N:8]=[CH:9][C:10]([NH:13]C(=O)OC(C)(C)C)=[N:11][CH:12]=2)[CH2:4][CH2:3][CH2:2]1.FC(F)(F)CO>>[CH:1]1([NH:5][CH2:6][C:7]2[N:8]=[CH:9][C:10]([NH2:13])=[N:11][CH:12]=2)[CH2:2][CH2:3][CH2:4]1

Participants

3

Reactant 2

HCID 64092,2,2-TrifluoroethanolHCID 66742355Tert-butyl 5-((cyclobutylamino)methyl)pyrazin-2-ylcarbamate

Product 1

HCID 667422585-Cyclobutylaminomethyl-pyrazin-2-ylamineYield 95%

Conditions

Temperature
150 °C

Procedure

In a 15 mL microwave tube was dissolved tert-butyl 5-((cyclobutylamino)methyl)pyrazin-2-ylcarbamate (330 mg, 1.19 mmol, Eq: 1.00) in 2,2,2-trifluoroethanol (119 mg, 12 ml, 1.19 mmol, Eq: 1.00) and the resulting mixture was heated in seal tube at 150° C. for 3 hrs. The crude reaction mixture was concentrated in vacuo, treated with MeOH and re-concentrated to remove residual trifluoroethanol. The material was azeotroped with toluene to afford 200 mg (95%) of the title compound.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated in vacuo
  3. additiontreated with MeOH
  4. concentrationre-concentrated
  5. customto remove residual trifluoroethanol
  6. customThe material was azeotroped with toluene

Sources & evidence

ORD record
ord-3423904cb6fb469fb56a43f889b9a6c1
Source dataset
uspto-grants-2015_01
Patent number
US08940741B2

Reaction notes

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