Sodium Methoxide → HCID 86717591, compound

HRID 715530Notes

Reaction equation

HRID 715530 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]([NH:8][C:9](=[O:13])[O:10][CH2:11]C)=[N:6][CH:7]=1.[CH3:14][O-:15].[Na+]>CO>[CH3:14][O:15][C:2]1[N:3]=[CH:4][C:5]([NH:8][C:9](=[O:13])[O:10][CH3:11])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86717592HCID 86717592, compound

Product 1

HCID 86717591HCID 86717591, compoundYield 22.01%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A 20 mL microwave vial was charged with ethyl (5-chloropyrazin-2-yl)carbamate (500 mg, 2.480 mmol) and 22% sodium methoxide in MeOH (10 mL). The tube was sealed and heated to 100° C. for 6 h. The reaction mixture was then concentrated, diluted between DCM and 2N HCl. The layers were separated and the aqueous layer was extracted with DCM (2×). The combined organic layers were washed with 2N HCl, brine, eluted through a phase separator and concentrated to afford methyl (5-methoxypyrazin-2-yl)carbamate as a brown oil (100 mg, 22.01% yield). MS (m/z) 184 (M+H+).

Workup

  1. customThe tube was sealed
  2. concentrationThe reaction mixture was then concentrated
  3. additiondiluted between DCM and 2N HCl
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with DCM (2×)
  6. washThe combined organic layers were washed with 2N HCl, brine
  7. washeluted through a phase separator
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-73a95f7629764fae8cfbf8e2776c9d9b
Source dataset
uspto-grants-2015_11
Patent number
US09187464B2

Reaction notes

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