Potassium Carbonate → HCID 83826394, compound

HRID 926379Notes

Reaction equation

HRID 926379 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[CH:5][C:6]([C:9]#[N:10])=[N:7][CH:8]=1.[CH3:11][Mg]Br.[BH4-].[Na+].[Cl-].[NH4+].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH3:1][O:2][C:3]1[N:4]=[CH:5][C:6]([CH:9]([NH2:10])[CH3:11])=[N:7][CH:8]=1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 534389935-Methoxypyrazine-2-carbonitrileHCID 178418573HCID 178418573, compound

Product 1

HCID 83826394HCID 83826394, compoundYield 4.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 5-methoxy-pyrazine-2-carbonitrile (1.0 g, 7.4 mmol) in tetrahydrofuran at −78° C. was added dropwise 1 M methylmagnesium bromide (8.14 ml, 8.14 mmol) and the mixture was stirred for 1 h at 25° C. Sodium borohydride (250 mg, 6.62 mmol) was added at −78° C. and the mixture was allowed to warm to 25° C. Aqueous ammonium chloride was added and after addition of excess potassium carbonate the mixture was extracted 3 times with dichloromethane, solvents were evaporated to give 0.05 g (4%) of crude 1-(5-methoxy-pyrazin-2-yl)-ethylamine. LC/MS (method 5): Rt=1.26 min; m/z=154.15 (M+H+).

Workup

  1. temperatureto warm to 25° C
  2. extractionwas extracted 3 times with dichloromethane, solvents
  3. customwere evaporated

Sources & evidence

ORD record
ord-51cec6153e5848f694da46ba6046785f
Source dataset
uspto-grants-2016_03
Patent number
US09284333B2

Reaction notes

Loading…