2-Propanol, sodium salt (1:1) → HCID 59273465, compound

HRID 2274040Notes

Reaction equation

HRID 2274040 reaction equation
Br[C:2]1[CH:7]=[N:6][C:5]([CH3:8])=[CH:4][N:3]=1.[CH3:9][CH:10]([O-:12])[CH3:11].[Na+]>CC(O)C>[CH:10]([O:12][C:2]1[CH:7]=[N:6][C:5]([CH3:8])=[CH:4][N:3]=1)([CH3:11])[CH3:9]

Participants

4

Reactant 2

HCID 109204432-Propanol, sodium salt (1:1)HCID 224193462-Bromo-5-methylpyrazine

Product 1

HCID 59273465HCID 59273465, compoundYield 37.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
115 °C

Procedure

To a solution of 2-bromo-5-methylpyrazine (3 g, 17.34 mmol) in 2-propanol (14 mL) was added sodium propan-2-olate (3.56 g, 43.3 mmol) and heated under microwave irradiation at 115° C. for 1.1 h. The organic solvent was evaporated before water was added to the residue. The mixture was extracted with dichloromethane (2×75 mL). The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a brown oil (1.0 g). LCMS m/z=153.4 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.27 (d, J=6.19 Hz, 6H), 2.39 (s, 3H), 5.10-5.20 (m, 1H), 7.84 (s, 1H), 7.99 (s, 1H).

Workup

  1. customThe organic solvent was evaporated before water
  2. additionwas added to the residue
  3. extractionThe mixture was extracted with dichloromethane (2×75 mL)
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d54c6e520c3d469a9409f1bf2326e9aa
Source dataset
uspto-grants-2015_09
Patent number
US09126932B2

Reaction notes

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