Methanol → HCID 68650622, compound

HRID 646740Notes

Reaction equation

HRID 646740 reaction equation
Cl[C:2]1[C:3]([C:14]([O:16][CH3:17])=[O:15])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][N:7]=1.[CH3:18][NH2:19].CO>O1CCCC1.C(OCC)(=O)C>[CH3:18][NH:19][C:2]1[C:3]([C:14]([O:16][CH3:17])=[O:15])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 6329MethylamineHCID 57698532HCID 57698532, compound

Product 1

HCID 68650622HCID 68650622, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
92.5 °C

Procedure

To a solution of methyl 3-chloro-6-phenylpyrazine-2-carboxylate (0.13 g, 0.53 mmol) in tetrahydrofuran (3 mL) was added 0.65 mL of 2.0 N methylamine in THF (1.30 mmol). The reaction was heated in a sealed high-pressure test tube to 90-95° C. overnight. The reaction was cooled to room temperature and diluted with ethyl acetate (100 mL). The organic layer was washed 2.0 N aqueous hydrochloric acid (20 mL), saturated aqueous sodium bicarbonate (30 mL), and saturated aqueous sodium chloride (30 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated at reduced pressure to afford a yellowish product. Trituration with methanol (2 mL) gave a solid, which was filtered and washed with ether to afford afford methyl 3-(methylamino)-6-phenylpyrazine-2-carboxylate (31 mg, 24%) as yellow solid: MS (EI) for C13H13N3O2: 244 (MH+). This intermediate ester was directly used in the next step.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. washThe organic layer was washed 2.0 N aqueous hydrochloric acid (20 mL), saturated aqueous sodium bicarbonate (30 mL), and saturated aqueous sodium chloride (30 mL)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated at reduced pressure
  6. customto afford a yellowish product
  7. filtrationwas filtered
  8. washwashed with ether
  9. customto afford

Sources & evidence

ORD record
ord-f61be1c0f10a473994e117835d082ab4
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

Loading…