Pyrrolidine → 5-(Pyrrolidin-1-yl)pyrazin-2-amine

HRID 250032Notes

Reaction equation

HRID 250032 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][CH2:10]1>C(OCC)(=O)C>[N:9]1([C:2]2[N:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 5995392-Amino-5-bromopyrazine

Product 1

HCID 250941545-(Pyrrolidin-1-yl)pyrazin-2-amineYield 43.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-bromopyrazin-2-amine (1.2 g, 6.9 mmol) and pyrrolidine (4 mL, 48 mmol) was microwaved at 180° C., 200 W for 2 h. The reaction was diluted into 125 mL ethyl acetate and extracted with water (3×50 mL) and brine (50 mL). It was dried over sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography (0 to 3% methanol/methylene chloride) to afford 5-(pyrrolidin-1-yl)pyrazin-2-amine (495 mg, 3. mmol, 43.7% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.52 (1 H, d, J=1.51 Hz), 7.36 (1 H, d, J=1.76 Hz), 5.21 (2H, s), 3.24-3.29 (4 H, m), 1.90 (4 H, ddd, J=6.48, 3.53, 3.34 Hz). MS (LC/MS) R.T.=0.52; [M+H]+=165.29.

Workup

  1. customwas microwaved at 180° C.
  2. extractionextracted with water (3×50 mL) and brine (50 mL)
  3. dry with materialIt was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (0 to 3% methanol/methylene chloride)

Sources & evidence

ORD record
ord-803fcb26aa49481396b3b1791be9648f
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Reaction notes

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