Potassium Carbonate → Tert-butyl 5-((cyclobutylamino)methyl)pyrazin-2-ylcarbamate

HRID 1431128Notes

Reaction equation

HRID 1431128 reaction equation
[CH:1]1([NH2:5])[CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].[C:12]([O:16][C:17](=[O:27])[NH:18][C:19]1[CH:24]=[N:23][C:22]([CH2:25]Br)=[CH:21][N:20]=1)([CH3:15])([CH3:14])[CH3:13]>C1COCC1>[C:12]([O:16][C:17](=[O:27])[NH:18][C:19]1[CH:24]=[N:23][C:22]([CH2:25][NH:5][CH:1]2[CH2:4][CH2:3][CH2:2]2)=[CH:21][N:20]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 75645CyclobutylamineHCID 45073740tert-Butyl (5-(bromomethyl)pyrazin-2-yl)carbamate

Product 1

HCID 66742355Tert-butyl 5-((cyclobutylamino)methyl)pyrazin-2-ylcarbamateYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a dried 100 mL round bottom flask was added cyclobutylamine (740 mg, 889 μl, 10.4 mmol, Eq: 3), K2CO3 (480 mg, 3.47 mmol, Eq: 1.00) and THF at rt. under argon. To the mixture was added a solution of (5-Bromomethyl-pyrazin-2-yl)-carbamic acid tert-butyl ester (1 g, 3.47 mmol, Eq: 1.00) in THF dropwise. The resulting reaction mixture was stirred vigorously at room temperature under argon overnight. The reaction was concentrated, diluted with water/DCM and extracted with DCM (2×30 mL). Combined organic extracts were concentrated to give a solid. The crude product was purified by LC chromatography (50 g spherical silica column) eluting with 5 to 10% MeOH in 1/1 EtOAc/Hex to afford 348 mg (36%) of the title compound as a white solid.

Workup

  1. customThe resulting reaction mixture
  2. concentrationThe reaction was concentrated
  3. additiondiluted with water/DCM
  4. extractionextracted with DCM (2×30 mL)
  5. concentrationCombined organic extracts were concentrated
  6. customto give a solid
  7. customThe crude product was purified by LC chromatography (50 g spherical silica column)
  8. washeluting with 5 to 10% MeOH in 1/1 EtOAc/Hex

Sources & evidence

ORD record
ord-15e98547a19440a29e1ff677a7ec0a4a
Source dataset
uspto-grants-2015_01
Patent number
US08940741B2

Reaction notes

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