5-Ethynylpyridin-3-amine → HCID 19911848, compound

HRID 1098590Notes

Reaction equation

HRID 1098590 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH2:9])[CH:6]=[N:7][CH:8]=1)#[CH:2]>CO.[Pd]>[CH2:1]([C:3]1[CH:4]=[C:5]([NH2:9])[CH:6]=[N:7][CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 210712745-Ethynylpyridin-3-amine

Product 1

HCID 19911848HCID 19911848, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-Ethynylpyridin-3-amine (0.122 g, 1.03 mmol) and 10% Pd/C (0.11 g, 0.102 mmol) were suspended in MeOH (15 mL). This was hydrogenated (42 psi) in a Parr hydrogenation apparatus overnight. The reaction was filtered through Celite® and washed forward with MeOH. The filtrate was concentrated to afford 5-ethylpyridin-3-amine (0.070 g, 56% yield) as a light yellow oil. 1H NMR (400 MHz, DMSO-d6): δ 7.72 (d, J=2.4 Hz, 1H), 7.58 (d, J=1.6 Hz, 1H), 6.71 (t, J=2.0 Hz, 1H), 5.16 (s, 2H), 2.43 (q, J=7.2 Hz, 2H), 1.11 (t, J=7.6 Hz, 3H).

Workup

  1. customin a Parr hydrogenation apparatus overnight
  2. filtrationThe reaction was filtered through Celite®
  3. washwashed forward with MeOH
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-c1d6eddd11ca47f49c5b0bfb477229a4
Source dataset
uspto-grants-2012_03
Patent number
US08143293B2

Reaction notes

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