5-(1-Azidoethyl)-2-methylpyrimidine → 1-(2-Methylpyrimidin-5-yl)ethanamine

HRID 241866Notes

Reaction equation

HRID 241866 reaction equation
[N:1]([CH:4]([C:6]1[CH:7]=[N:8][C:9]([CH3:12])=[N:10][CH:11]=1)[CH3:5])=[N+]=[N-]>[Pd].C(OCC)(=O)C>[CH3:12][C:9]1[N:10]=[CH:11][C:6]([CH:4]([NH2:1])[CH3:5])=[CH:7][N:8]=1

Participants

4

Reactant 1

HCID 581035925-(1-Azidoethyl)-2-methylpyrimidine

Product 1

HCID 552838311-(2-Methylpyrimidin-5-yl)ethanamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-(1-azidoethyl)-2-methylpyrimidine (2.20 g, 12.8 mmol), ethyl acetate (170 mL), and 10% palladium on carbon (1.32 g) was stirred under hydrogen (1 atm) overnight. The mixture was filtered and concentrated. The residue was purified by silica gel column (0-50% MeOH/EtOAc with 10% Et3N) to afford a colorless oil. 1H NMR (300 MHz, CD3OD): 8.71 (s, 2H), 4.12 (q, 1H, J=6.6 Hz), 2.67 (s, 3H), 1.44 (d, J=6.6 Hz, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel column (0-50% MeOH/EtOAc with 10% Et3N)
  4. customto afford a colorless oil

Sources & evidence

ORD record
ord-7c20bfa690624439a99bbe70cf1a6a31
Source dataset
uspto-grants-2014_02
Patent number
US08653091B2

Reaction notes

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