Potassium Carbonate → HCID 57629918, compound

HRID 1875899Notes

Reaction equation

HRID 1875899 reaction equation
Br[C:2]1[N:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[NH:9]1[CH2:13][CH2:12][CH2:11][C:10]1=[O:14].C(=O)([O-])[O-].[K+].[K+].[C@@H]1(N)CCCC[C@H]1N>O1CCOCC1.[Cu]I.CO.C(OCC)(=O)C>[NH2:8][C:5]1[N:6]=[CH:7][C:2]([N:9]2[CH2:13][CH2:12][CH2:11][C:10]2=[O:14])=[N:3][CH:4]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 120252-PyrrolidoneHCID 438061,2-Diaminocyclohexane, trans-HCID 5995392-Amino-5-bromopyrazine

Product 1

HCID 57629918HCID 57629918, compoundYield 30.7%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-bromopyrazin-2-amine (5 g, 29 mmol), pyrrolidin-2-one (11 mL, 144 mmol), copper (I) iodide (1.1 g, 5.75 mmol), potassium carbonate (7.94 g, 57.5 mmol), and (1R,2R)-cyclohexane-1,2-diamine (1.38 mL, 11.49 mmol) was refluxed under nitrogen in dioxane (100 mL) for 18 h. After cooling, 200 mL ethyl acetate and 20 mL methanol were added to the reaction. This was filtered through celite, concentrated, and absorbed onto sodium sulfate for purification by column chromatography (0-5% methanol/methylene chloride). The purified product was recrystallized from ether/ethyl acetate to afford 1-(5-aminopyrazin-2-yl)pyrrolidin-2-one (1.57 g, 8.81 mmol, 30.7% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.74 (1H, d, J=1.51 Hz), 7.69 (1H, d, J=1.51 Hz), 6.20 (2H, s), 3.84 (2H, t, J=7.05 Hz), 2.49 (2H, t, J=7.93 Hz), 2.04 (2H, dq, J=7.68, 7.51 Hz). MS (LC/MS) R.T.=0.48; [M+H]+=179.27.

Workup

  1. temperatureAfter cooling
  2. filtrationThis was filtered through celite,
  3. concentrationconcentrated
  4. customabsorbed onto sodium sulfate for purification by column chromatography (0-5% methanol/methylene chloride)
  5. customThe purified product was recrystallized from ether/ethyl acetate

Sources & evidence

ORD record
ord-07b3bd0c71244cbb9465fc88bccba4ff
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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