5-Amino-3-chloropyrazine-2-carbonitrile → 5-Amino-3-methoxypyrazine-2-carbonitrile

HRID 556881

Reaction equation

HRID 556881 reaction equation
[NH2:1][C:2]1[N:3]=[C:4](Cl)[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[CH3:11][O-:12].[Na+].CO>CO.O>[NH2:1][C:2]1[N:3]=[C:4]([O:12][CH3:11])[C:5]([C:8]#[N:9])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 210753925-Amino-3-chloropyrazine-2-carbonitrileHCID 23694274Sodium methanolate methanol

Product 1

HCID 596133845-Amino-3-methoxypyrazine-2-carbonitrileYield 58%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

5-Amino-3-chloropyrazine-2-carbonitrile (52 mg, 0.34 mmol) was suspended in NaOMe/MeOH (2M, 2 mL). The reaction mixture was heated at 80° C. for 30 min using microwave irradiation. After cooling, the mixture was diluted with MeOH (3 mL) and water (2 mL). The solvents were concentrated and the resulting precipitate was filtered off, washed with water (3 mL) and dried in vacuo to give the title compound as a yellow solid (33 mg, 58%).

Workup

  1. custommicrowave irradiation
  2. temperatureAfter cooling
  3. concentrationThe solvents were concentrated
  4. filtrationthe resulting precipitate was filtered off
  5. washwashed with water (3 mL)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-3225739478654ae88199617ad3e4528c
Source dataset
uspto-grants-2011_11
Patent number
US08058045B2

Linked notes

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