Ethanol → Ethyl 5-methylpyrazine-2-carboxylate

HRID 1832001Notes

Reaction equation

HRID 1832001 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.[CH2:11](O)[CH3:12]>>[CH3:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 702EthanolHCID 1228315-Methyl-2-pyrazinecarboxylic acid

Product 1

HCID 16114819Ethyl 5-methylpyrazine-2-carboxylateYield 67%

Procedure

A solution of 5-methylpyrazine-2-carboxylic acid (15.0 g, 0.109 mol) in ethanol (70.0 mL) containing (1.5 g, 0.0079 mol) was heated to reflux for 4 h under argon atmosphere. The dark colored solution was cooled, added sod.bicarbonate (1.0 g) and concentrated under reduced pressure. The residue was partitioned between water (50 mL) and EtOAc (100 mL). The organic layer was washed with water (2×25 mL), dried (Na2SO4), and concentrated under reduced pressure to afford ethyl 5-methylpyrazine-2-carboxylate (12.05 g, 67%) as an orange colored liquid: 1H NMR (CD3OD/400 MHz) δ 9.1 (d. 1H, J=1.2 Hz), 8.62 (d, 1H, J=1.2 Hz), 4.45 (q, 2H, J=7.2 Hz), 2.63 (s, 3H), and 1,41 (t, 3H, J=7.2 Hz); ES MS m/z 167 (M+H). Step 2 Ethyl 5-(bromomethyl)pyrazine-2-carboxylate

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h under argon atmosphere
  3. temperatureThe dark colored solution was cooled
  4. additionadded sod
  5. concentrationbicarbonate (1.0 g) and concentrated under reduced pressure
  6. customThe residue was partitioned between water (50 mL) and EtOAc (100 mL)
  7. washThe organic layer was washed with water (2×25 mL)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d78b16f446744252b8bcdd805cfd4575
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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